Is There a Chrome Extension for Breezeway?

Yes. There is one Chrome extension built for Breezeway: RapidEye, which adds one-click AI damage detection to your turnover photos. Here is what it does and what Breezeway offers natively.

# Is there a Chrome extension for Breezeway?

There is one Chrome extension built specifically for Breezeway: RapidEye, which adds one-click AI damage detection to the turnover photos Breezeway already stores. Breezeway itself does not publish an official browser extension; it delivers its product through the Breezeway web platform and mobile app.

If you searched for this, you probably noticed the results are a mess. Most of them point to unrelated products named **"Breeze"** (website managers, task trackers, new-tab tools) that have nothing to do with Breezeway, the property operations platform used by [270,000 properties across 90 countries](https://www.breezeway.io/about). So let's answer the actual question cleanly.

## What Breezeway offers natively

Breezeway is a web-based property operations platform with a companion mobile app for cleaners and inspectors in the field. That is by design. According to Breezeway, the mobile app is where field staff work through checklists, capture photos, and mark tasks complete, while the web platform is where managers coordinate everything. There is no official Breezeway browser extension, and for most of what the platform does, you would not need one.

### Breezeway, natively

- Web platform for managers

- Mobile app for field staff

- Checklists with photo capture

- Task scheduling and tracking

### Added via Chrome extension

- AI analysis of turnover photos

- Damage and missing-item detection

- Itemized damage report

- One click, no workflow change

## The one extension built for Breezeway

The gap a browser extension fills is analysis. Breezeway captures and stores your turnover photos beautifully, but reviewing every image for damage across a portfolio is a manual job. That is exactly what the RapidEye extension automates.

Adds an "Analyze latest 5 tasks" button to your Breezeway properties page. According to RapidEye, one click analyzes the photos from your five most recently completed turnovers with AI and a damage report is emailed to you, typically within one business day. The extension is free to install and your first analysis is complimentary, with no API keys or setup required.

We wrote a full walkthrough of how it works in our [RapidEye Chrome extension for Breezeway](https://rapideyeinspections.com/blog/rapideye-chrome-extension-breezeway/) post, including screenshots of the one-click flow and what the report looks like.

**A note on the search confusion:** "Breeze" and "Breezeway" are different products. The Breeze extensions in the Chrome Web Store (website management, task management) are unrelated to Breezeway the vacation rental operations platform. If you use Breezeway for turnovers, the RapidEye extension is the one built for you.

## What about other AI tools for Breezeway?

A Chrome extension is one way to add capability. Most Breezeway users also layer in other specialized tools that connect via Breezeway's integrations rather than the browser. For the full picture, see our guide to [AI tools that work with Breezeway in 2026](https://rapideyeinspections.com/blog/ai-tools-that-work-with-breezeway/), which covers pricing, messaging, and damage detection. If you specifically want to understand the damage-analysis side, [adding AI damage detection to your Breezeway workflow](https://rapideyeinspections.com/blog/add-ai-damage-detection-breezeway-workflow/) goes deeper on the integration options beyond the extension.

## Frequently asked questions

## Sources

- [RapidEye Inspections - Chrome Web Store](https://chromewebstore.google.com/detail/rapideye-inspections/lpelonobdodfaapaejodmgacpgigfkoc)
https://chromewebstore.google.com/detail/rapideye-inspections/lpelonobdodfaapaejodmgacpgigfkoc

- [About Breezeway](https://www.breezeway.io/about)
https://www.breezeway.io/about


The Largest Short-Term Rental Management Companies (2026)

The ranked 2026 breakdown of the largest short-term rental property management companies by units managed. Casago-Vacasa combined, Evolve, Awaze, AvantStay, Grand Welcome. Every number cited to primary sources.

# The Largest Short-Term Rental Management Companies, 2026

A ranked, sourced account of who runs the most vacation rentals in 2026 — and why the list looks very different than it did eighteen months ago.

The largest short-term rental property manager in North America is **Casago**, which manages approximately 43,000 vacation homes after closing its acquisition of Vacasa on May 1, 2025. Evolve is second with more than 30,000 properties, followed by legacy regional operators and a small set of fast-growing urban apartment-hotel brands.

Globally, the largest vacation rental manager is **Awaze**, a Platinum Equity portfolio company that operates more than 110,000 units across 36 countries in Europe, built from Wyndham's 2018 divestiture of its vacation rental business for 1.3 billion dollars.

The list looks meaningfully different than it did in early 2024. Vacasa lost 97 percent of its public market value before being taken private at 47.4 million dollars. Sonder peaked at roughly 17,100 total units in 2023 and filed for Chapter 7 liquidation in November 2025, with approximately 9,000 units still operating when Marriott terminated its licensing agreement. Consolidation is now the dominant force in the industry.

This ranking counts **units managed by each operator under a property management or hospitality operator model**, based on the most recent publicly reported figure from each company. Every number is cited inline and at the bottom. Vacasa figures come from its final 10-K for FY2024 and the Casago-Vacasa closing press release; Sonder figures from the Q3 2023 investor update, the last reliable snapshot before the portfolio-optimization drawdown.

We separate **pure property managers** (Vacasa, Evolve, AvantStay) from **channel aggregators** (RedAwning). Both "manage listings" but do fundamentally different things for the owner, and we flag the distinction in the table.

## The Ranking

| # | Company | Units | Primary Geography | Archetype |
| --- | --- | --- | --- | --- |
| 1 | AwazeEurope's largest, from Wyndham spin-out | 110,000+ | 36 countries, Europe | European Multi-Brand |
| 2 | RedAwningAggregator / marketplace, not a traditional PM | 100,000+ | Global, US-based | Channel / Aggregator |
| 3 | Casago (incl. Vacasa)Largest North American property manager, post-May 2025 merger | ~43,000 | North America, Belize, Costa Rica | Full-Service Franchise |
| 4 | EvolveTech-enabled lean model, Denver-based, profitable | 30,000+ | US and Mexico, 750+ markets | Tech-Lean Platform |
| 5 | VTripsAcquisition roll-up, Florida-based | ~7,000 | 8 states, 35+ markets | Full-Service Regional |
| 6 | OnefinestayLuxury homes, Accor-owned, Exclusive Resorts partnership | 5,000 | Global luxury destinations | Luxury Specialist |
| 7 | AvantStayLuxury group travel focus, equity-backed | ~2,300 | 140+ US cities | Luxury Specialist |
| 8 | Grand WelcomeFranchise network, US-focused | 2,200+ | 50+ US cities, 18 states | Full-Service Franchise |
| 9 | SkyRunFranchise network, each location locally owned | 950–1,000+ | 30+ North American markets | Full-Service Franchise |
| 10 | KasaApart-hotel operator, revenue-share model | ~80 properties | Major US urban markets | Urban Apart-Hotel |
| 11 | PlacemakrApartment-hotel hybrid, Hilton partnership | Growing rapidly | US urban markets | Urban Apart-Hotel |
| — | SonderChapter 7 liquidation, November 2025 | 0 | Previously 40+ cities | Defunct |

## The Five Archetypes

Every operator fits one of five archetypes. The archetype matters more than the unit count because it determines how the company makes money and what it actually does for owners.

### Full-Service Property Manager

Operator takes full responsibility for pricing, cleaning, maintenance, guest communication, and owner accounting. Typically 20-35 percent of revenue. Thin margins; this is where the most consolidation has happened.

### Tech-Enabled Lean Platform

Software-forward. Operator handles pricing, distribution, and messaging; owners source local cleaning and maintenance. Lower fees (~10 percent), higher scale. Evolve is the only US operator in the top five publicly known to be profitable.

### Luxury Specialist

Curated high-end portfolios. Smaller unit counts (2,000-5,000), much higher nightly rates. AvantStay's reported $5B AUM on ~2,300 homes implies more than $2M per property in asset value.

### Urban Apart-Hotel

Operator leases or revenue-shares entire buildings and runs them as branded hospitality products. Placemakr's 2024 Hilton partnership under the Apartment Collection by Hilton brand signals that hotel majors now see this category as strategic.

### European Multi-Brand Federation

Holding company running a portfolio of distinct national brands. Dominates European vacation rentals by unit count but has minimal US presence. More hospitality conglomerate than traditional PM.

## The 2024-2026 Consolidation Timeline

The story is simple: the full-service model was structurally unprofitable at the venture-funded scale Vacasa and Sonder tried to reach, and the industry has been absorbing that reality.

UK-based Houst absorbs rival Hostmaker, becoming one of Europe's largest short-term rental managers outside of Awaze. An early sign that the model was consolidating.

According to the closing announcement, Vacasa paid approximately 45 million dollars in cash and 573.8 million dollars in stock. Post-acquisition, Vacasa managed approximately 30,000 homes and became the largest North American vacation rental manager.

Vacasa combines with TPG Pace Solutions and lists on the Nasdaq under the ticker VCSA. The deal raises approximately 340 million dollars in cash, below the 485 million originally targeted. Shares open at 10 dollars and close the first day at 9.84 dollars. Vacasa has never reported an annual profit.

Sonder closes its business combination with Gores Metropoulos II on January 18, 2022, and begins trading on the Nasdaq under the ticker SOND the next day. Gores Metropoulos II discloses 96 percent redemptions on the deal.

At Q3 2023, Sonder reports approximately 17,100 total portfolio units of which 11,800 are "live." Sonder announces it will exit or reduce rent on approximately 105 buildings and 4,300 units. By mid-2024 the optimization is complete; total portfolio shrinks by roughly 25 percent.

Sonder hotels are added to Marriott's Bonvoy distribution system. The deal is described internally and in the trade press as a "lifeline."

Casago offers 5.02 dollars per share for all outstanding Vacasa shares held by public stockholders. At the time of the announcement, Vacasa's self-reported home count was 38,000. A rival proposal from Davidson Kempner surfaces briefly.

The revised offer lifts the deal value to approximately 47.4 million dollars. Vacasa's board recommends it.

The combined company manages approximately 43,000 vacation homes across North America, Belize and Costa Rica. Vacasa's common stock ceases trading on the Nasdaq after 1,242 days as a public company. The transition to a franchise-led operating model begins.

Accor retains a stake but hands operational control of its luxury vacation rental brand to Exclusive Resorts, signaling that even the hotel majors are rethinking direct ownership of vacation rental operators.

Marriott cites integration delays and revenue decline from Bonvoy distribution issues. Sonder loses its distribution lifeline overnight.

Guests are told to vacate rooms with less than 24 hours of notice. Sonder's assets and liabilities are each estimated in the multi-billion-dollar range. The company has approximately 5,001 to 10,000 creditors.

Schwab moves from CEO to Chairman of the Board after completing the Vacasa integration's first phase. The transition positions Casago to operate as a post-founder franchise brand at scale.

## Deep-Dive Profiles

Short profiles on the operators that matter most for anyone benchmarking their own business.

Founded by Steve Schwab in 2001, Casago spent two decades as a regional franchise operation with roughly 5,000 properties across 72 destinations. The Vacasa acquisition was a step-change. According to the Casago press release, the combined company now manages approximately 43,000 vacation homes.

Casago is unusual among full-service operators in running a true franchise structure: local operators license the brand and technology stack, but run their own markets. Schwab told [PhocusWire](https://www.phocuswire.com/casago-vacasa-deal-closes-steve-schwab) this is why the deal worked where Vacasa's fully company-owned model had not: franchisees carry the ops cost and accountability, removing the structural margin problem that sunk Vacasa's public company.

Founded by Brian Egan and Adam Sherry in 2011, Evolve is the leanest operator in the top five and, per [VRM Intel's profile of Egan](https://vrmintel.com/how-brian-egan-built-evolve-into-a-profitable-short-term-rental-business-whats-next-for-vacation-rentals/), the only US-headquartered operator at scale publicly known to be profitable.

Evolve's structural advantage is that it does not own or manage the local cleaning and maintenance crews. Owners source their own vetted crews from a partner network, while Evolve centralizes listing distribution, dynamic pricing, guest messaging, and accounting. The ~10 percent fee (vs 25-35 percent at full-service peers) reflects this split.

Awaze was formed when Platinum Equity acquired Wyndham Worldwide's European vacation rental business for approximately $1.3 billion in 2018. The company operates a federation of national brands: cottages.com and Hoseasons in the UK, James Villa Holidays, Novasol in Denmark, and Landal GreenParks in the Netherlands.

Awaze is the clearest example of the multi-brand federation archetype: it got to the top of the global unit-count ranking by buying and operating existing brands rather than building a single consumer-facing monolith.

AvantStay is the US luxury leader by unit count. According to [a December 2021 announcement](https://www.finsmes.com/2021/12/avantstay-raises-160m-in-series-b-funding.html), the company closed a $160M Series B led by Tarsadia Investments and 3L Capital, followed by a separate $500M propco fund led by Saluda Grade in February 2022 — one of the first short-term rental propcos ever created.

The operating model combines traditional property management with group-travel product design: most homes are 4+ bedrooms, set up for families and corporate retreats, with curated interior fit-outs standardized across the portfolio. AvantStay's reported $5B AUM on ~2,300 homes works out to more than $2M per property in asset value.

VTrips is the clearest example of the roll-up model in US vacation rentals. Founder Steve Milo launched the company as Vacation Rental Pros around 2005 and grew it through acquisitions of regional operators in leisure markets (Florida, Gulf Coast, Blue Ridge, the Smokies). Per [a 2023 acquired-brand announcement](https://silversandsvacationrentals.com/news/vtrips-expands-portfolio-to-7000-vacation-rentals-1000-employees), VTrips reached ~7,000 rentals and ~1,000 employees. Milo stepped down as CEO in early 2025; Scott Seay, previously COO, succeeded him.

VTrips matters because its model — buying regional operators and integrating them — is what Casago is now attempting at larger scale post-Vacasa. Its track record will inform whether the Casago playbook works.

Operators in this category lease or revenue-share entire buildings and run them as branded hospitality products blending short-term, extended-stay, and hotel demand. Kasa operates ~80 properties, roughly 60 percent apartment-style and 40 percent boutique-hotel, and has raised ~$125M across three rounds.

In 2024, Hilton launched Apartment Collection by Hilton, combining ~3,000 units from Placemakr with 10,000 of Hilton's own. Placemakr [announced profitability in June 2024](https://www.prnewswire.com/news-releases/placemakr-announces-a-transition-to-profitability-in-june-2024-302220143.html), an unusual disclosure in this segment. The category is still small by units but bridges vacation rentals and hotels, and the Hilton partnership is a signal that the majors see it as strategic.

## Postmortem: How Sonder Collapsed

Sonder filed for Chapter 7 one day after Marriott terminated the Bonvoy licensing agreement that had been described as its lifeline. The interim CEO's court filing cited "unexpected challenges in aligning our technology frameworks" and a revenue decline when Sonder bookings moved through Bonvoy.

The deeper cause was structural. Sonder signed long-term leases on hotel and apartment buildings, fit them out under its brand, and filled them with nightly guests. When demand held up, the model worked; when demand softened, the leases did not flex. The November 2023 portfolio-optimization program (exiting or reducing rent on ~105 buildings and 4,300 units) was an attempt to fix this by renegotiating obligations downward, but the company couldn't shed leases fast enough.

**Same failure mode as WeWork.** A long-lease, urban-density, brand-forward model looks like hospitality during growth and real estate during contraction — and it's the real estate side of the ledger that kills the company. Kasa, Placemakr, and the other apart-hotel operators have structured around revenue-share rather than long leases, which is at least part of the bet behind Hilton's Apartment Collection partnership with Placemakr.

## What the Top Operators Have in Common

Three operational patterns are consistent across the top ten, and they matter more than the unit counts.

### Franchise or revenue-share beats fully-owned at scale

The fully company-owned, venture-funded, growth-at-all-costs model failed. Vacasa and Sonder both tried variants; neither produced an annual profit before being acquired or liquidated. The operators growing or profitable today (Casago, Evolve, SkyRun, Grand Welcome, Placemakr, Kasa) all push operational responsibility and cost to a layer they do not fully own — franchisees, local cleaning networks, owners, or building partners. The winning playbook isn't "raise capital and acquire units," it's "design a model where unit growth doesn't require proportional ops cost growth."

### Everyone scales past 5,000 units on in-house technology

Vacasa built proprietary dynamic pricing and a smart-home stack (locks, thermostats, noise monitors via Vacasa Connect), folding in TurnKey's technology after the 2021 acquisition. Evolve built centralized infrastructure for pricing, messaging, and distribution from the start. No one scales past ~5,000 units on off-the-shelf software alone.

### Turnover quality is the binding operational constraint

Across the top ten, turnover quality — clean, inspected, ready for the next guest — is consistently identified as the biggest variable in both guest scores and owner retention. Following the Casago acquisition, reviewers have flagged [service-quality variance during franchisee handovers](https://rapideyeinspections.com/blog/ai-damage-detection-accuracy-false-positives-trust/) as a real operational risk, which is why [AI turnover inspection](https://rapideyeinspections.com/blog/best-ai-turnover-inspection-short-term-rentals-2026/) is growing quickly among operators in the 200-unit-plus range.

## What This Means for Mid-Market Operators

For operators in the 100-to-1,000-unit range, three things follow from the above. First, **M&A in this segment will accelerate:** Casago now has a franchise infrastructure that can absorb an independent 500-unit regional operator in a way Vacasa's company-owned model could not, and the same is true of VTrips, Grand Welcome, and SkyRun. Second, **the lean-platform model (Evolve) is underrated:** most mid-market operators default to full-service because it's the legible model, but Evolve's 30,000+ profitable homes at a ~10 percent fee structure is proof that full-service is not the only scaling path. Third, **the operational premium is real:** AvantStay's $5B AUM on 2,300 homes is a concrete benchmark for what curation and operational excellence are worth, and the compounding effect on guest scores, ADR, repeat bookings, and owner retention over 24 months is larger than most operators budget for.

## Frequently Asked Questions

As of 2026, the largest short-term rental property manager in North America is Casago, which manages approximately 43,000 vacation homes following its May 1, 2025 acquisition of Vacasa. Evolve is second with more than 30,000 properties in the US and Mexico.

Vacasa is no longer an independent company. It operates under Casago ownership after the May 1, 2025 acquisition closed. The combined Casago-Vacasa entity manages approximately 43,000 vacation homes across North America, Belize and Costa Rica. Vacasa's last 10-K filing, for fiscal year 2024, reported 36,500 homes managed as of December 31, 2024.

Casago, an Arizona-based vacation rental franchise company founded in 2001 by Steve Schwab. Casago acquired Vacasa for approximately 47.4 million dollars in a merger that closed on May 1, 2025. Vacasa's common stock is no longer traded on the Nasdaq.

Sonder Holdings filed for Chapter 7 liquidation in November 2025 after Marriott International terminated their licensing agreement on November 9, 2025. Guests were given less than 24 hours to vacate their rooms. Sonder operated approximately 9,000 units across more than 40 cities at the time of collapse. The company had been public since January 2022 via a SPAC merger and had never reported an annual profit. The structural cause was a long-lease operating model that could not flex its cost base when demand softened.

By the time the Casago merger was announced in December 2024, Vacasa's public market value had fallen by approximately 97 percent from its December 2021 SPAC listing. The company had reported losses every year since inception (154 million dollars in 2021, 177 million in 2022, 299 million in 2023, 154.9 million in 2024) and was operating under structural cost pressure that the public market was no longer willing to underwrite. The final enterprise value at the Casago take-private was approximately 47.4 million dollars. The underlying business, with 36,500 homes and nearly 1 billion dollars of gross booking value, remained operationally significant; the public company structure did not.

According to public statements from Evolve CEO Brian Egan and reporting in VRM Intel, Evolve has been profitable and maintaining profitability was a deliberate strategic choice versus pursuing higher-growth-but-loss-making models. Evolve is the only US-headquartered vacation rental operator at scale (30,000+ homes) publicly known to be profitable.

The Skift Short-Term Rental 250 and the Comparent 100 are the industry's widely cited ranked lists of short-term rental operators, and both are useful references. This report focuses specifically on operator scale (units managed), organizes by operating archetype, and pairs each number with an inline primary source. Where our ranking differs from those lists, it is typically because we separate pure property managers from channel aggregators and marketplaces, which those lists sometimes combine.

### How the biggest operators handle turnover inspection

Damage and condition issues slip through manual inspection at scale. RapidEye automates this layer and plugs into Breezeway, Guesty, and Streamline PropertyCare. Built by Carnegie Mellon researchers.

## Sources

- [Casago Completes Acquisition of Vacasa — Vacasa press release](https://www.vacasa.com/news/casago-completes-vacasa-acquisition)https://www.vacasa.com/news/casago-completes-vacasa-acquisition

- [Vacasa Is Now a Casago Company After Acquisition Closes — Skift (May 1, 2025)](https://skift.com/2025/05/01/vacasa-is-now-a-casago-company-after-acquisition-closes/)https://skift.com/2025/05/01/vacasa-is-now-a-casago-company-after-acquisition-closes/

- [Vacasa Accepts Revised Acquisition Proposal from Casago at $5.30 Per Share — BusinessWire](https://www.businesswire.com/news/home/20250317051316/en/Vacasa-Accepts-Revised-Acquisition-Proposal-from-Casago-at-$5.30-Per-Share)https://www.businesswire.com/news/home/20250317051316/en/Vacasa-Accepts-Revised-Acquisition-Proposal-from-Casago-at-$5.30-Per-Share

- [Vacasa Inc. Form 10-K for fiscal year ended December 31, 2024 — SEC filing](https://www.sec.gov/Archives/edgar/data/1874944/000187494425000003/vcsa-20241231.htm)https://www.sec.gov/Archives/edgar/data/1874944/000187494425000003/vcsa-20241231.htm

- [STR management company Casago acquires much larger — but struggling — Vacasa — PhocusWire](https://www.phocuswire.com/str-management-casago-acquires-vacasa)https://www.phocuswire.com/str-management-casago-acquires-vacasa

- [Casago's Steve Schwab on finalizing Vacasa and what lies ahead — PhocusWire](https://www.phocuswire.com/casago-vacasa-deal-closes-steve-schwab)https://www.phocuswire.com/casago-vacasa-deal-closes-steve-schwab

- [Sonder Holdings Inc. To Complete Immediate Wind-Down of Operations — Sonder investor relations](https://investors.sonder.com/news-releases/news-release-details/sonder-holdings-inc-complete-immediate-wind-down-operations)https://investors.sonder.com/news-releases/news-release-details/sonder-holdings-inc-complete-immediate-wind-down-operations

- [Sonder announces bankruptcy plans; tells guests to vacate — CNBC (November 11, 2025)](https://www.cnbc.com/2025/11/11/sonder-to-file-for-bankruptcy-travelers-told-to-leave-hotels-next-day.html)https://www.cnbc.com/2025/11/11/sonder-to-file-for-bankruptcy-travelers-told-to-leave-hotels-next-day.html

- [Sonder Officially Shuts Down: What Went Wrong? — Skift](https://skift.com/2025/11/10/sonder-officially-shuts-down-what-went-wrong/)https://skift.com/2025/11/10/sonder-officially-shuts-down-what-went-wrong/

- [Marriott, Sonder implosion detailed in court filing — Hotel Dive](https://www.hoteldive.com/news/marriott-sonder-termination-bankruptcy-court-filing/805975/)https://www.hoteldive.com/news/marriott-sonder-termination-bankruptcy-court-filing/805975/

- [Vacasa Finalizes Acquisition of TurnKey Vacation Rentals — Vacasa press release (April 2021)](https://www.vacasa.com/news/vacasa-finalizes-acquisition-turnkey-vacation-rentals)https://www.vacasa.com/news/vacasa-finalizes-acquisition-turnkey-vacation-rentals

- [Vacasa Paid $619 Million for TurnKey Vacation Rentals in Mostly Stock — Skift](https://skift.com/2021/11/30/vacasa-paid-619-million-for-turnkey-vacation-rentals-in-mostly-stock/)https://skift.com/2021/11/30/vacasa-paid-619-million-for-turnkey-vacation-rentals-in-mostly-stock/

- [Vacasa just went public. Here are five things to know — OPB (December 2021)](https://www.opb.org/article/2021/12/07/vacasa-ipo-price-portland-oregon-based-companies-vacation-rentals-stock-market/)https://www.opb.org/article/2021/12/07/vacasa-ipo-price-portland-oregon-based-companies-vacation-rentals-stock-market/

- [Vacation-Rental SPAC Vacasa Restructures. Shares -97% in 2.5 Years as Public Company — Wolf Street](https://wolfstreet.com/2024/05/10/vacation-rental-spac-vacasa-restructures-shares-97-in-2-5-years-as-public-company/)https://wolfstreet.com/2024/05/10/vacation-rental-spac-vacasa-restructures-shares-97-in-2-5-years-as-public-company/

- [What the Largest Vacation Rental Companies in the U.S. Really Look Like in 2025 — Rental Scale-Up](https://www.rentalscaleup.com/largest-vacation-rental-companies-us-2025/)https://www.rentalscaleup.com/largest-vacation-rental-companies-us-2025/

- [How Brian Egan Built Evolve Into a Profitable Short-Term Rental Business — VRM Intel](https://vrmintel.com/how-brian-egan-built-evolve-into-a-profitable-short-term-rental-business-whats-next-for-vacation-rentals/)https://vrmintel.com/how-brian-egan-built-evolve-into-a-profitable-short-term-rental-business-whats-next-for-vacation-rentals/

- [Awaze, A Platinum Equity Portfolio Company — Platinum Equity](https://www.platinumequity.com/our-company/awaze/)https://www.platinumequity.com/our-company/awaze/

- [Europe's $1.3B vacation rental giant gets a new name (Awaze) — The Real Deal](https://therealdeal.com/new-york/2019/03/09/come-awaze-with-me-europes-1-3b-vacation-rental-giant-gets-a-new-name/)https://therealdeal.com/new-york/2019/03/09/come-awaze-with-me-europes-1-3b-vacation-rental-giant-gets-a-new-name/

- [Rental Company AvantStay Raises $160 Million — LA Business Journal](https://labusinessjournal.com/real-estate/rental-company-avantstay-raises-160-million/)https://labusinessjournal.com/real-estate/rental-company-avantstay-raises-160-million/

- [Short-Term Rental Company AvantStay Raises $500 Million (propco) — LA Business Journal](https://labusinessjournal.com/news/weekly-news/short-term-rental-company-avantstay-raises-500-million/)https://labusinessjournal.com/news/weekly-news/short-term-rental-company-avantstay-raises-500-million/

- [VTrips Expands Portfolio To 7,000 Vacation Rentals, 1,000 Employees — Silver Sands](https://silversandsvacationrentals.com/news/vtrips-expands-portfolio-to-7000-vacation-rentals-1000-employees)https://silversandsvacationrentals.com/news/vtrips-expands-portfolio-to-7000-vacation-rentals-1000-employees

- [Exclusive Resorts Takes Stake in Accor's Onefinestay — Skift (June 24, 2025)](https://skift.com/2025/06/24/exclusive-resorts-takes-stake-in-accors-onefinestay-exclusive/)https://skift.com/2025/06/24/exclusive-resorts-takes-stake-in-accors-onefinestay-exclusive/

- [Placemakr Announces a Transition to Profitability in June 2024 — PRNewswire](https://www.prnewswire.com/news-releases/placemakr-announces-a-transition-to-profitability-in-june-2024-302220143.html)https://www.prnewswire.com/news-releases/placemakr-announces-a-transition-to-profitability-in-june-2024-302220143.html

- [Hilton Launches Apt. Brand, Placemakr Partnership — Business Travel News](https://www.businesstravelnews.com/Lodging/Hilton-Launches-Apt-Brand-Placemakr-Partnership)https://www.businesstravelnews.com/Lodging/Hilton-Launches-Apt-Brand-Placemakr-Partnership

- [Kasa Living Raises $70M — AlleyWatch (November 2023)](https://www.alleywatch.com/2023/11/kasa-living-flexible-accommodations-hospitality-brand-tech-enabled-roman-pedan/)https://www.alleywatch.com/2023/11/kasa-living-flexible-accommodations-hospitality-brand-tech-enabled-roman-pedan/

- [Steve Schwab founder profile — Casago](https://casago.com/Steve-Schwab/)https://casago.com/Steve-Schwab/

- [Grand Welcome Announces it has Surpassed 750 Short-Term Vacation Rental Properties — Grand Welcome](https://www.grandwelcome.com/blog/press_links/grand-welcome-announces-it-has-surpassed-750-short-term-vacation-rental-properties-in-the-u-s/)https://www.grandwelcome.com/blog/press_links/grand-welcome-announces-it-has-surpassed-750-short-term-vacation-rental-properties-in-the-u-s/

- [SkyRun Vacation Rentals Franchising page — SkyRun](https://skyrun.com/franchising/)https://skyrun.com/franchising/

## Related Reading


The Largest Vacation Rental Management Companies in Florida (2026)

A sourced 2026 ranking of the largest vacation rental management companies in Florida, by region, with unit counts. Casago-Vacasa, VTrips, Prime Vacations, Panhandle Getaways, 360 Blue. Built on the VRMA member directory.

# The Largest Vacation Rental Management Companies in Florida, 2026

Florida has more professional vacation rental managers than any other state. Here is who runs the most homes, ranked and sourced, plus a region-by-region map of the country's biggest short-term rental market.

The largest vacation rental manager operating in Florida is **Casago**, the franchise company that acquired Vacasa in May 2025 and runs roughly 40,000 homes across North America. Vacasa built its Florida presence largely by acquiring the Gulf Coast operator Sterling Resorts in 2019, and still runs homes across Destin, 30A, Panama City Beach, and Orlando, while the tech-enabled platform **Evolve** lists homes throughout the state.

The largest vacation rental company headquartered in Florida is **VTrips**, based in Ponte Vedra near Jacksonville, with about 7,000 rentals across the Southeast. Among independent operators based in Florida, the largest are **Prime Vacations** (~1,000 homes on Anna Maria Island), **Panhandle Getaways** (900+ on the Emerald Coast), and **360 Blue** (~700 on 30A).

Florida is the most concentrated vacation rental management market in the United States: **718 management companies** name Florida as their home state in the VRMA directory, nearly double California's 443. The single densest region is not Orlando but the **Emerald Coast and 30A** Panhandle, which accounts for about 31 percent of all professionally managed units reported in the state.

This report separates two groups. **Tier 1** is national operators with significant Florida portfolios; their unit counts are company-wide totals from public sources, not Florida-only figures, because these companies do not publish per-state counts. **Tier 2** is the largest operators headquartered in Florida, ranked by the number of units they self-reported to the Vacation Rental Management Association (VRMA) member directory as of March 2026.

VRMA figures are operator self-reported and not independently audited; we corroborate the largest against company websites and press, and we use the operator's own published figure where one exists. We exclude companies headquartered outside Florida (for example Nocturne Luxury Villas, a Rhode Island holding company), brands owned by the national roll-ups (Jeeves is now a Casago brand; Distinctive Beach Rentals and Southern Vacation Rentals belong to VTrips), single-resort rental desks, HOA and timeshare programs, and software vendors, so the list reflects third-party vacation rental management. Founding years and PMS data also come from the VRMA directory. The directory snapshot is from March 2026; company-website figures were verified in June 2026. Every external number is cited inline and listed with its URL at the end.

## Florida is the country's biggest management market

Before ranking individual companies, it helps to see the scale of the field. According to the March 2026 VRMA member directory, no state comes close to Florida's count of professional vacation rental management companies.

VRMA member companies by home state, March 2026 directory. Counts members that list each state as their headquarters.

The takeaway is not just that Florida is big, it is that Florida's management market is **fragmented**. A median founding year of 2014 (among the 438 Florida members that reported one) and a long tail of small operators means there is no single dominant local brand the way there is in some smaller ski or beach markets. Hundreds of independent managers compete alongside the national platforms, which is exactly why a sourced ranking is useful.

## Florida is really eight markets

Vacation rental management in Florida does not behave as one statewide market. It is a set of distinct coastal and theme-park economies, each with its own leading operators. Grouping the 328 unit-reporting members by region reveals where the homes actually are.

Self-reported managed units among the 328 Florida VRMA members that reported a unit count, grouped by the region of their headquarters city. About 1,400 additional units sit with members in smaller or statewide markets not shown.

### The Panhandle, not Orlando, is Florida's management heartland

Most people assume Orlando and Disney drive Florida's vacation rental industry. By raw professional management concentration, they are wrong. The **Emerald Coast and 30A** corridor (Destin, Miramar Beach, Santa Rosa Beach, and Panama City Beach) holds about **8,900 self-reported managed units across 62 companies**, roughly 31 percent of the nearly 29,000 units reported statewide and more than the Orlando theme-park corridor.

The reason is structural. The Panhandle is overwhelmingly a whole-home beach market built for professional management, while Orlando's inventory skews toward owner-managed condos and large branded resort programs that do not all run through independent VRMs. For an operator deciding where to expand or who to benchmark against, the Panhandle is the most competitive professional arena in the state.

## Tier 1: National operators with major Florida portfolios

These are the largest companies running vacation rentals in Florida. Their unit counts are company-wide totals, not Florida-only figures, because none publish per-state breakdowns.

| # | Company | Total units | Florida footprint |
| --- | --- | --- | --- |
| 1 | Casago (incl. Vacasa) NationalLargest North American manager, post-2025 merger | ~40,000 | Entered via Sterling Resorts & ResortQuest (2019); Destin, 30A, PCB, Orlando |
| 2 | Evolve NationalTech-enabled lean platform, half-service model | 30,000+ | Florida markets within 750+ US and Mexico markets |
| 3 | VTrips FL HQLargest Florida-headquartered operator, a roll-up | ~7,000 | HQ Ponte Vedra; Gulf Coast, Panhandle, statewide |

## Tier 2: The largest Florida-headquartered operators

Independent operators that call Florida home, ranked by the units they self-reported to the VRMA member directory in March 2026. These are the regional brands that, together, manage the bulk of Florida's professionally run inventory.

| # | Company | Unitsself-reported | Region / HQ |
| --- | --- | --- | --- |
| 1 | Prime VacationsAnna Maria Island, founded 2017 | ~1,000company | SW Gulf Coast / Anna Maria |
| 2 | Panhandle GetawaysBeach rentals, 30-plus years on the coast | 900+company | Emerald Coast / Panama City Beach |
| 3 | 360 BlueLuxury 30A homes, founded 2008, part of Natural Retreats | ~700company | Emerald Coast / Santa Rosa Beach |
| 4 | Royal Shell VacationsLargest in SW Florida, began 1996 | 500+on Sanibel | SW Gulf Coast / Sanibel Island |
| 5 | Ocean Reef Vacation RentalsFounded 1982 | ~528company | Emerald Coast / Destin |
| 6 | RoamiFormerly Sextant Stays, founded 2016 | ~500company | South Florida / Miami |
| 7 | Scenic StaysFounded 2018 | ~450VRMA | Emerald Coast / Destin |
| 8 | Benchmark ManagementFounded 2017 | ~420VRMA | Emerald Coast / Santa Rosa Beach |
| 9 | Luxury Coastal VacationsFounded 2007 | ~330VRMA | Emerald Coast / Pensacola |
| 10 | Cape & Coast Premier PropertiesFounded 2016 | ~290VRMA | Forgotten Coast / Port St. Joe |

## Who leads each Florida region

The statewide ranking hides the local reality: most Florida owners hire by region. Here is the leading independent operator picture in each major market, drawn from the same directory.

### Emerald Coast / 30A

**Panhandle Getaways**, **360 Blue**, **Ocean Reef**, **Scenic Stays**, and **Benchmark** lead the Panhandle, alongside Vacasa's Sterling Resorts brand. The densest professional market in the state.

### Orlando / Theme Parks

**Jeeves** (now a Casago brand) and a long tail of Disney-area villa managers in Davenport, Kissimmee, and Reunion. High volume, but more owner-managed condos than the beaches.

### SW Gulf Coast

**Prime Vacations** (Bradenton) and **Royal Shell** (Sanibel) anchor the Naples, Sarasota, Fort Myers, and Marco Island markets.

### Atlantic / NE Florida

**VTrips** is headquartered in Ponte Vedra in this region, which spans Jacksonville, Amelia Island, St. Augustine, and the Space Coast. It is more fragmented than the beaches, with no single dominant independent brand.

### South Florida

**Roami** (formerly Sextant Stays) and **Portoro** lead a Miami and Fort Lauderdale market that is more urban and condo-driven than the rest of the state.

### Forgotten Coast & the Keys

**Cape & Coast** and **Collins Vacation Rentals** on the quiet Forgotten Coast; a small, tightly held set of operators in the Florida Keys.

These cards cover the six largest regions by managed units; the remaining members report from Tampa Bay and smaller or statewide markets.

## Three operators that define the Florida market

VTrips is the largest vacation rental company headquartered in Florida and the clearest example of the roll-up model in US vacation rentals. Founder Steve Milo launched it as Vacation Rental Pros in 2002 and grew it by acquiring regional operators in Florida, the Gulf Coast, the Blue Ridge, and the Smokies. According to [VTrips](https://www.prnewswire.com/news-releases/vtrips-expands-portfolio-to-7-000-vacation-rentals-1-000-employees-301565493.html), the company now manages more than 7,000 rentals across 35 markets in 10 states with about 1,000 employees.

Its Florida growth came by acquisition: VTrips bought Southern Vacation Rentals (about 1,120 Panhandle and Alabama homes) in 2022, plus Resort Collection in Panama City Beach and Distinctive Beach Rentals in Fort Myers Beach. That playbook, buying local brands and integrating them onto a shared operations stack, is the consolidation pattern now reshaping the state.

Vacasa built its Florida footprint through acquisition. According to [ShortTermRentalz](https://shorttermrentalz.com/news/vacasa-sterling-resorts-purchase/), Vacasa acquired Sterling Resorts, a Gulf Coast operator running about 450 homes, on April 15, 2019, establishing its Northwest Florida presence, and still markets those homes across Destin, 30A, and Panama City Beach. Later in 2019 it acquired Wyndham Vacation Rentals, which brought the [ResortQuest](https://www.vacasa.com/partners/resortquest) brand long associated with the Florida Panhandle.

Vacasa was acquired by the Arizona franchise company Casago in May 2025; the combined company manages approximately 40,000 homes across North America. Its Florida operation spans the Panhandle and Orlando, making Casago-Vacasa the largest single manager of Florida vacation homes despite the absence of a published state-level count.

Panhandle Getaways is among the largest independent, family-owned managers on Florida's Emerald Coast, a market it has worked for more than 30 years. According to its website, it manages over 900 condos and beach homes across Panama City Beach, 30A, Destin, Fort Walton, and the Forgotten Coast. It is the kind of established regional operator, deep in one coastline rather than spread thin across the country, that defines how Florida's professional inventory is actually run, and the kind of brand the national roll-ups target for acquisition.

Its scale on a single stretch of coast is a reminder that in Florida, regional depth often beats national breadth: the operators who dominate a beach know its rental calendar, its repair vendors, and its owners better than any platform can.

## What the data says about Florida's market

### It is consolidating, but slowly

Florida's combination of 718 management companies and a median founding year of 2014 describes a young, fragmented field. National roll-ups (Casago-Vacasa, Evolve, VTrips) are buying their way in, but no single brand controls the state. The independents in Tier 2 still collectively manage far more homes than any one national platform's Florida slice, which is why local reputation and regional depth remain the currency of the market.

### Legacy software still runs the coast

Among Florida VRMA members that reported a property management system, **Streamline** is the most common (54 companies), followed by HomeAway and Vrbo software products (37), Ciirus (19), LiveRez (11), Guesty (10), and Hostaway (9). That legacy-heavy mix is notable: while the newest companies nationally lean toward Hostaway and Guesty, Florida's established beach operators still run older, deeply embedded systems. We unpack that generational split in our [analysis of the vacation rental PMS market](https://rapideyeinspections.com/blog/vacation-rental-pms-generational-shift/).

### Scale makes turnover quality the binding constraint

The operators on this list run hundreds to thousands of homes across multiple beaches and theme-park submarkets, which makes consistent turnover inspection the hardest operational problem they face. A 900-home Emerald Coast manager handling back-to-back summer Saturdays is reviewing tens of thousands of cleaning and condition photos a season. That volume is exactly where [AI turnover inspection](https://rapideyeinspections.com/blog/best-ai-turnover-inspection-short-term-rentals-2026/) is being adopted fastest among operators in the 200-home-plus range.

## Frequently asked questions

The largest manager operating in Florida is Casago, which acquired Vacasa in May 2025 and runs roughly 40,000 homes across North America. Vacasa entered Florida by acquiring the Gulf Coast operators Sterling Resorts and Wyndham Vacation Rentals (ResortQuest) in 2019. The largest company headquartered in Florida is VTrips, based in Ponte Vedra near Jacksonville, with about 7,000 rentals. Among independent Florida-based operators, the largest is Prime Vacations on Anna Maria Island, with about 1,000 homes.

As of the March 2026 VRMA member directory, 718 member companies list Florida as their home state, more than any other US state and nearly double California's 443. Of those, 328 reported a unit count, totaling roughly 29,000 self-reported managed homes. The true number of all Florida vacation rental managers is higher, since not every operator is a VRMA member.

The Emerald Coast and 30A region of the Panhandle (Destin, Miramar Beach, Santa Rosa Beach, and Panama City Beach) leads, with about 8,900 self-reported managed units across 62 companies, roughly 31 percent of the nearly 29,000 units reported statewide. That is more than the Orlando theme-park corridor, contradicting the common assumption that Orlando dominates Florida vacation rental management.

Yes. Vacasa, now owned by Casago, is one of the largest vacation rental managers in Florida. It acquired Sterling Resorts, a Gulf Coast operator with about 450 homes, on April 15, 2019, and still markets those homes across Destin, 30A, and Panama City Beach. Vacasa also operates in Orlando and other Florida markets.

VTrips, headquartered in Ponte Vedra near Jacksonville, is the largest. It was founded in 2002 by Steve Milo as Vacation Rental Pros and grew through acquisitions of regional operators in Florida, the Gulf Coast, the Blue Ridge, and the Smokies. VTrips says it now manages more than 7,000 rentals across 35 markets in 10 states with about 1,000 employees.

### How Florida's largest operators keep turnover quality consistent at scale

Across hundreds of beach and theme-park homes, damage and cleaning issues slip through manual photo review. RapidEye automates that inspection layer and plugs into Breezeway, Guesty, and Streamline PropertyCare. Built by Carnegie Mellon researchers.

## Sources

- [Vacation Rental Management Association (VRMA) public member directory, March 2026 compilation (state, units, founding year, PMS)](https://www.vrma.org/)https://www.vrma.org/

- [Why has Vacasa decided to purchase Sterling Resorts in Florida? - ShortTermRentalz (April 2019, 450 Gulf Coast homes)](https://shorttermrentalz.com/news/vacasa-sterling-resorts-purchase/)https://shorttermrentalz.com/news/vacasa-sterling-resorts-purchase/

- [ResortQuest is now managed by Vacasa - Vacasa (Northwest Florida)](https://www.vacasa.com/partners/resortquest)https://www.vacasa.com/partners/resortquest

- [Casago Completes Acquisition of Vacasa - Vacasa press release (May 2025, ~40,000 homes)](https://www.vacasa.com/news/casago-completes-vacasa-acquisition)https://www.vacasa.com/news/casago-completes-vacasa-acquisition

- [VTrips Expands Portfolio to 7,000 Vacation Rentals, 1,000 Employees - PR Newswire (HQ Ponte Vedra, founded 2002, 10 states)](https://www.prnewswire.com/news-releases/vtrips-expands-portfolio-to-7-000-vacation-rentals-1-000-employees-301565493.html)https://www.prnewswire.com/news-releases/vtrips-expands-portfolio-to-7-000-vacation-rentals-1-000-employees-301565493.html

- [VTrips Announces Acquisition of Southern Vacation Rentals - PR Newswire (April 2022, +1,120 properties; Resort Collection & Distinctive Beach Rentals)](https://www.prnewswire.com/news-releases/vtrips-announces-acquisition-of-southern-vacation-rentals-301533790.html)https://www.prnewswire.com/news-releases/vtrips-announces-acquisition-of-southern-vacation-rentals-301533790.html

- [About Us - Prime Vacations (founded 2017, Anna Maria Island, 1,000+ rentals)](https://primevacations.com/about-us/)https://primevacations.com/about-us/

- [Panhandle Getaways (900+ condos and beach homes, Emerald Coast)](https://www.panhandlegetaways.com/)https://www.panhandlegetaways.com/

- [Natural Retreats Acquires 360 Blue - PR Newswire (Sept 9, 2020, 700+ Gulf Coast properties)](https://www.prnewswire.com/news-releases/natural-retreats-acquires-360-blue-301126788.html)https://www.prnewswire.com/news-releases/natural-retreats-acquires-360-blue-301126788.html

- [Royal Shell Vacations (500+ Sanibel/Captiva homes, largest in Southwest Florida, since 1996)](https://www.royalshell.com/)https://www.royalshell.com/

- [Ocean Reef Vacation Rentals & Real Estate (528 properties, founded 1982, Destin/30A)](https://www.oceanreefresorts.com/)https://www.oceanreefresorts.com/

- [Sextant Stays becomes Roami - TechCrunch (March 2023, 500 units, founded 2016)](https://techcrunch.com/2023/03/07/sextant-stays-becomes-roami/)https://techcrunch.com/2023/03/07/sextant-stays-becomes-roami/

- [What the Largest Vacation Rental Companies in the U.S. Really Look Like - Rental Scale-Up (Evolve 30,000+)](https://www.rentalscaleup.com/largest-vacation-rental-companies-us-2025/)https://www.rentalscaleup.com/largest-vacation-rental-companies-us-2025/

## Related Reading


listo is a photo-verified turnover inspection app that gives cleaning teams room-by-room checklists with reference photos. Here is how it works, what the OK / Not OK flow looks like, and why structured photo capture is the natural input for AI damage detection like RapidEye.

# What Is listo? Photo-Verified Turnover Inspections for Short-Term Rentals

Getting consistent turnover photos out of cleaners is one of the hardest parts of running rentals remotely. [listo](https://checklis.to/) is a newer app built to fix exactly that, and the structured photo record it produces happens to be the perfect input for AI damage detection.

listo is a photo-verified turnover inspection app for short-term rental hosts and property managers. It gives cleaning teams room-by-room checklists with reference photos that show how each space should look before the next guest arrives, then captures a timestamped verification photo for every item, marked OK or Not OK. The result is a structured record tied to a property, room, item, timestamp, and status, instead of a pile of random photos in a text thread.

That structure is also why listo pairs naturally with AI damage detection. listo handles capture; a tool like RapidEye handles analysis, comparing those photos against a per-property baseline to flag damage, missing items, and cleanliness failures. Capture first, intelligence on top.

If you have ever tried to manage a short-term rental remotely, you know the photo problem. Cleaners walk the property and snap whatever they happen to think of that day, and they miss a lot. The photos end up scattered across text messages, WhatsApp groups, shared albums, and individual phones. According to listo, that is how most operators still document turnovers, and it makes three things hard at once: reviewing the right photos quickly, proving when damage actually happened, and knowing whether a property was genuinely guest-ready before check-in.

listo organizes that process so every inspection photo is tied to a property, a room, a checklist item, a timestamp, and a status. The headline framing on its own site, "Set 5-star standards. Get 5-star reviews," and "Your properties. Your rules. Your proof," points at the same idea: turn each changeover into a documented, verifiable record rather than a judgment call.

## What the OK / Not OK Flow Actually Looks Like

The core mechanic is simple. Each checklist item shows a reference photo of how that space or object is supposed to look. The cleaner frames their verification shot against it, then marks the item OK or Not OK and can leave a note. Here is a real checklist detail view from the app:

**Bathtub.** The verification photo matches the reference. The item passes, timestamped to the exact minute it was checked, so there is a record the bathtub was clean before arrival.

**Soap Container.** Flagged with a note straight from the cleaner: "we're out of hand soap. please buy more." The issue is logged against the item the moment it is found, not relayed three messages later in a group chat.

Source: listo app, Checklist Details screen. Each item carries a status, a photo, and a capture timestamp.

The value of this is not the checkbox. It is that the photo is captured *against a reference*. "Photo verification" stops meaning "snap something" and starts meaning "frame this shot like this one." A host can eyeball the difference in seconds, and every property ends up with a documented prep state for every single changeover.

## Two Layers of Turnover Documentation

It helps to think about turnover documentation as two distinct jobs. One job is **capturing** the right photos consistently. The other is **analyzing** those photos for problems a person scrolling quickly will miss. They are different problems, and they are best solved by different tools.

### listo prep verification, in the cleaner's hand

Reference-guided, room-by-room photo checklists. Every item gets a verification photo, an OK / Not OK status, an optional note, and a timestamp. The output is a consistent, organized photo record for each turnover.

### RapidEye condition analysis, after capture

Compares the captured photos against a per-property baseline built from listing photos, Matterport scans, reference images, and prior inspections, then surfaces damage, missing items, and cleanliness failures with severity, so the operator reviews a short list instead of a full album.

The two layers are genuinely complementary rather than competitive. listo captures the data in a consistent operational workflow; RapidEye analyzes that data. A host ends up with a verified "this is how the property looked before the guest arrived" record, and an AI read on what changed and what needs attention.

## Why Consistent Capture Makes AI Detection Work

This is the part operators tend to underrate. AI damage detection is only as good as the photos it receives. When a model has to compare a wide, evenly-lit shot of a living room from one turnover against a dark close-up of a couch cushion from the next, the comparison gets noisy and false positives climb. When the same item is photographed the same way every turnover, because the cleaner is framing against a fixed reference, the comparison gets clean and the real changes stand out.

That is the quiet reason a capture tool and an analysis tool belong together. RapidEye's approach is built on per-property baseline comparison, the same method we describe in [how baseline comparison catches what inspections miss](https://rapideyeinspections.com/blog/ai-baseline-comparison-catches-what-inspections-miss/). A baseline only works if new photos are comparable to it. listo's reference-photo workflow produces exactly that comparability. Better capture upstream means fewer false positives and more caught damage downstream. According to RapidEye's internal trial data, across more than 1.5 million turnover photos at a 500-plus unit property manager, the analysis surfaced an average of four missed damages per property, the kind of findings that only hold up when the photos feeding them are consistent.

## How the Combined Workflow Runs

### The cleaner opens listo and works the checklist

Each item shows a reference photo. The cleaner frames their shot to match it, room by room.

### Every item gets a status and a timestamp

OK or Not OK, with an optional note like "out of hand soap." The record is tied to the property, room, and item automatically.

### The turnover produces one organized photo set

Instead of photos scattered across phones and group chats, there is a single, reviewable prep record for that changeover.

### RapidEye compares the photos to the property's baseline

The analysis layer checks the captured images against listing photos, Matterport scans, and prior inspections for that exact unit.

### The operator reviews a short list of findings

Flagged damage, missing items, and cleanliness issues with severity, instead of eyeballing an entire album hoping to spot the one problem.

The two teams have discussed a direct integration so flagged items could flow from listo into RapidEye automatically. listo has published its own walkthrough of the pairing, [AI issue detection with RapidEye](https://checklis.to/blog/ai-issue-detection-rapideye), from the capture side. Even without a built integration, the workflow holds: consistent capture in one tool, automated condition analysis in the other.

## listo at a Glance

The details below come from [listo's own product site](https://checklis.to/) and overview. As always, confirm current specifics and pricing directly with the vendor.

#### Reference-guided capture

Side-by-side reference and verification photos, item by item, so cleaners frame the shot instead of guessing.

#### Six languages

The cleaner-facing app supports English, Spanish, French, German, Italian, and Portuguese.

#### Five-minute setup

No hardware and no implementation project, per listo. A property can be live the same morning.

#### Timestamped history

A complete inspection record per property, with each photo carrying its own capture time.

#### Multi-property dashboard

Built for managers overseeing multiple units and multilingual teams, not just single-listing hosts.

#### Issue and supply tracking

Failed items and supply replenishment (like that out-of-soap flag) are logged as they are found.

listo handles the capture problem well, and for operators who do not yet have a structured way to collect turnover photos, that alone is a meaningful upgrade over group chats. Where it stops, by design, is automated analysis: it organizes the evidence, but it does not tell you what changed since the last guest. That is the layer RapidEye adds. If you already capture turnover photos through [Breezeway](https://www.breezeway.io/), Guesty, or Streamline PropertyCare, the same analysis layer applies; the capture tool just changes.

### Already capturing turnover photos? See what RapidEye catches in them

RapidEye is AI-powered inspection intelligence built by two Carnegie Mellon researchers. It analyzes the turnover photos and video your team already captures and flags damage, missing items, and cleanliness failures, an average of four missed damages per property in one 1.5M-photo trial.

## Frequently Asked Questions

### What is listo?

listo is a photo-verified turnover inspection app for short-term rental hosts and property managers. It gives cleaning teams room-by-room checklists with reference photos that show how each space and item should look before the next guest arrives. As a team member completes each item, they capture a verification photo and mark it OK or Not OK, creating a timestamped record tied to a specific property, room, checklist item, and status. According to listo, setup takes about five minutes with no hardware, and the cleaner-facing app supports six languages: English, Spanish, French, German, Italian, and Portuguese.

### How does listo work with AI damage detection like RapidEye?

listo and RapidEye are complementary layers. listo handles capture: it standardizes how turnover photos are taken so every changeover produces a consistent, timestamped set of images instead of scattered shots in a group chat. RapidEye handles analysis: it compares those photos against a per-property baseline built from listing photos, Matterport scans, reference images, and prior inspections to flag damage, missing items, and cleanliness failures. Consistent capture is exactly what makes downstream AI analysis reliable, which is why the two stacks fit together: listo at turnover prep, RapidEye for post-stay condition analysis.

### Does listo do damage detection?

No. listo is a capture and prep-verification tool, not a damage-detection engine. It organizes turnover documentation so a host can eyeball the difference between a reference photo and a verification photo, and it lets a cleaner flag an item as Not OK with a note. It does not automatically compare photos against a learned baseline or surface missed damage and missing items. That analysis layer is what a tool like RapidEye adds on top of the photo record listo collects.

## Sources

- listo. [listo product site](https://checklis.to/). Photo-verified turnover checklists for vacation rental hosts and property managers: room-by-room reference photos, six-language cleaner app, five-minute setup. Taglines "Set 5-star standards. Get 5-star reviews." and "Your properties. Your rules. Your proof."
 https://checklis.to/

- listo product overview and app screenshot provided directly by founder Moshik Raccah, May 2026 (direct correspondence). Source of the OK / Not OK flagging flow, timestamped per-item records, and the scattered-photos problem the app is built to solve.

- listo. [AI issue detection with RapidEye](https://checklis.to/blog/ai-issue-detection-rapideye). listo's own write-up of how its photo capture pairs with RapidEye's analysis layer.
 https://checklis.to/blog/ai-issue-detection-rapideye

- RapidEye Inspections. Internal trial data from a 500-plus unit short-term rental property manager: over 1.5 million turnover photos analyzed, average of four missed damages per property. Per-property baseline built from listing photos, Matterport scans, reference images, and prior inspections. Available on request through a product demonstration.
 https://rapideyeinspections.com

## Related


We mapped 50 Massachusetts vacation rental management companies from the VRMA directory: the largest operators, top-5 concentration (65%), dominant software, and what the data means. Primary-source figures, cleaned.

# Massachusetts Vacation Rental Management Companies: The 2026 Market in Numbers

We pulled every Massachusetts member of the national vacation rental managers’ association and ranked the market by the numbers: how many companies, who manages the most units, how concentrated it is, and what software runs it.

**Massachusetts is home to 50 VRMA-member vacation rental management companies**, of which 20 disclosed a unit count totaling 3,115 managed units. The market is best described as a concentrated, operator-led market.

The largest reporting operator is **Sandpiper Rentals, Inc.** at roughly 650 units. The top five reporting operators control about 65 percent of all units disclosed, the most common property management system among members is Streamline, and the median member company was founded around 2005.

## 01Massachusetts at a glance

VRMA member companies headquartered in Massachusetts, March 2026.

## 02The largest operators

Ranked by self-reported units managed. Figures are disclosed by the operators themselves.

| # | Operator | Units (self-reported) |
| --- | --- | --- |
| 1 | Sandpiper Rentals, Inc.Edgartown | 650 |
| 2 | Kinlin Grover Compass Vacation RentalsBrewster | 501 |
| 3 | Del Mar VacationsOrleans | 350 |
| 4 | Point B Realty, LLCVineyard Haven | 275 |
| 5 | Martha Murray Vacation RentalsDennis Port | 250 |
| 6 | New England Vacation Rentals Inc.Chatham | 230 |
| 7 | South End HospitalityJamaica Plain | 225 |
| 8 | Pretty Picky PropertiesBrewster | 199 |
| 9 | oldCape Sotheby's International RealtyOrleans | 125 |
| 10 | Maverick SuitesBoston | 105 |

## 03How concentrated is the market?

The five largest reporting operators control about **65 percent** of every unit disclosed by Massachusetts members. That is unusually concentrated, the mark of a resort-anchored market.

## 04What software runs the market

Most-named property management systems among Massachusetts members.

According to the VRMA directory, the unit-heavy incumbents in Massachusetts still lean on Streamline and legacy HomeAway/Escapia systems, the same generational pattern we documented across the whole industry in [the PMS market analysis](https://rapideyeinspections.com/blog/vacation-rental-pms-generational-shift/).

## 05What the data says

According to the VRMA public member directory (compiled March 2026), Massachusetts has 50 member vacation rental management companies, of which 20 disclosed a unit count totaling 3,115 managed units. The largest reporting operator is Sandpiper Rentals, Inc. at roughly 650 units, and the top five reporting operators hold about 65 percent of disclosed units, making Massachusetts unusually concentrated for its size.

Most Massachusetts members are small independents rather than large portfolio operators; the median member company was founded around 2005. Among members that named a property management system, Streamline is the most common, consistent with the broader industry pattern in which Streamline and legacy HomeAway and Escapia systems still run most unit-heavy incumbents.

## 06Compare other states

Figures come from RapidEye's analysis of the **VRMA (Vacation Rental Management Association) public member directory**, compiled March 2026. Counts cover companies that list a Massachusetts headquarters. Unit counts are **self-reported**; only 20 of 50 Massachusetts members disclosed one, so the 3,115-unit total is a floor, not a census of every short-term rental in the state.

We de-duplicated companies that appear under multiple brand spellings (keeping the higher figure) and excluded entries whose self-reported totals reflect national franchise networks, timeshare or HOA portfolios, or brands since acquired and folded into a national operator. Massachusetts required only standard de-duplication; no national-franchise, timeshare, or HOA totals needed to be removed.

## 07Sources

- VRMA (Vacation Rental Management Association) — Public Member Directory, compiled March 2026 (primary data set).https://www.vrma.org/search/newsearch.asp

- RapidEye — The Largest Short-Term Rental Management Companies (2026).https://rapideyeinspections.com/blog/largest-short-term-rental-management-companies/

- RapidEye — The Vacation Rental PMS Market Just Flipped: 40 Years in One Chart.https://rapideyeinspections.com/blog/vacation-rental-pms-generational-shift/

## 08Frequently asked

### How many vacation rental management companies are in Massachusetts?

According to the VRMA public member directory compiled in March 2026, Massachusetts has 50 member vacation rental management companies. Of those, 20 disclosed a unit count, together reporting 3,115 managed units.

### Who is the largest vacation rental management company in Massachusetts?

Based on self-reported figures in the VRMA directory, the largest reporting operator in Massachusetts is Sandpiper Rentals, Inc. with approximately 650 units. The five largest reporting operators together account for about 65 percent of all units disclosed by Massachusetts members.

### What property management software do Massachusetts vacation rental companies use?

Among Massachusetts members that named a property management system, Streamline is the most common, consistent with the broader pattern in which Streamline and legacy HomeAway/Escapia systems still run most unit-heavy incumbents.


We mapped 61 Michigan vacation rental management companies from the VRMA directory: the largest operators, top-5 concentration (45%), dominant software, and what the data means. Primary-source figures, cleaned.

# Michigan Vacation Rental Management Companies: The 2026 Market in Numbers

We pulled every Michigan member of the national vacation rental managers’ association and ranked the market by the numbers: how many companies, who manages the most units, how concentrated it is, and what software runs it.

**Michigan is home to 61 VRMA-member vacation rental management companies**, of which 32 disclosed a unit count totaling 2,092 managed units. The market is best described as a moderately concentrated market.

The largest reporting operator is **Jaqua Vacation Rentals by Jaqua Realtors** at roughly 250 units. The top five reporting operators control about 45 percent of all units disclosed, the most common property management system among members is Guesty, and the median member company was founded around 2012.

## 01Michigan at a glance

VRMA member companies headquartered in Michigan, March 2026.

## 02The largest operators

Ranked by self-reported units managed. Figures are disclosed by the operators themselves.

| # | Operator | Units (self-reported) |
| --- | --- | --- |
| 1 | Jaqua Vacation Rentals by Jaqua RealtorsSouth Haven | 250 |
| 2 | Real Property Management Southwest MichiganSaint Joseph | 200 |
| 3 | Northern Michigan EscapesBoyne City | 180 |
| 4 | LiveSuitesGrand Rapids | 171 |
| 5 | Freshwater Vacation Rentals, LLCWyandotte | 149 |
| 6 | Juniper Holiday + HomeUnion Pier | 140 |
| 7 | Visit Up North Vacation Rentals, LLCTraverse City | 125 |
| 8 | Elevated Homes & HospitalityTraverse City | 96 |
| 9 | Shores Vacation RentalsSouth Haven | 85 |
| 10 | Unique Stays, LLCNiles | 85 |

## 03How concentrated is the market?

The five largest reporting operators control about **45 percent** of every unit disclosed by Michigan members. That is a middle-of-the-road split typical of established markets.

## 04What software runs the market

Most-named property management systems among Michigan members.

According to the VRMA directory, the unit-heavy incumbents in Michigan still lean on Streamline and legacy HomeAway/Escapia systems, the same generational pattern we documented across the whole industry in [the PMS market analysis](https://rapideyeinspections.com/blog/vacation-rental-pms-generational-shift/).

## 05What the data says

According to the VRMA public member directory (compiled March 2026), Michigan has 61 member vacation rental management companies, of which 32 disclosed a unit count totaling 2,092 managed units. The largest reporting operator is Jaqua Vacation Rentals by Jaqua Realtors at roughly 250 units, and the top five reporting operators hold about 45 percent of disclosed units, making Michigan a middle-of-the-road split.

Most Michigan members are small independents rather than large portfolio operators; the median member company was founded around 2012. Among members that named a property management system, Guesty is the most common, consistent with the broader industry pattern in which Streamline and legacy HomeAway and Escapia systems still run most unit-heavy incumbents.

## 06Compare other states

Figures come from RapidEye's analysis of the **VRMA (Vacation Rental Management Association) public member directory**, compiled March 2026. Counts cover companies that list a Michigan headquarters. Unit counts are **self-reported**; only 32 of 61 Michigan members disclosed one, so the 2,092-unit total is a floor, not a census of every short-term rental in the state.

We de-duplicated companies that appear under multiple brand spellings (keeping the higher figure) and excluded entries whose self-reported totals reflect national franchise networks, timeshare or HOA portfolios, or brands since acquired and folded into a national operator. Michigan required only standard de-duplication; no national-franchise, timeshare, or HOA totals needed to be removed.

## 07Sources

- VRMA (Vacation Rental Management Association) — Public Member Directory, compiled March 2026 (primary data set).https://www.vrma.org/search/newsearch.asp

- RapidEye — The Largest Short-Term Rental Management Companies (2026).https://rapideyeinspections.com/blog/largest-short-term-rental-management-companies/

- RapidEye — The Vacation Rental PMS Market Just Flipped: 40 Years in One Chart.https://rapideyeinspections.com/blog/vacation-rental-pms-generational-shift/

## 08Frequently asked

### How many vacation rental management companies are in Michigan?

According to the VRMA public member directory compiled in March 2026, Michigan has 61 member vacation rental management companies. Of those, 32 disclosed a unit count, together reporting 2,092 managed units.

### Who is the largest vacation rental management company in Michigan?

Based on self-reported figures in the VRMA directory, the largest reporting operator in Michigan is Jaqua Vacation Rentals by Jaqua Realtors with approximately 250 units. The five largest reporting operators together account for about 45 percent of all units disclosed by Michigan members.

### What property management software do Michigan vacation rental companies use?

Among Michigan members that named a property management system, Guesty is the most common, consistent with the broader pattern in which Streamline and legacy HomeAway/Escapia systems still run most unit-heavy incumbents.


When Is an Airbnb Damage Claim Worth Filing? Threshold Math for Multi-Unit Operators

The break-even math for filing an Airbnb damage claim at scale. Ops labor cost vs. expected recovery, scenario analysis at $100 to $2,500 claim amounts, and a filing threshold policy template for 100+ unit property managers.

## 01 / The hidden costEvery claim costs ops time, filed or not

Property managers who run 5 to 10 units file every claim. The ops cost is the owner's own time and there is no meaningful labor budget to protect. At 100-plus units, that logic breaks. A claim is no longer "free" because an ops coordinator has to document, file, and follow up on it instead of doing other work. Every claim draws from the same labor pool as turnover coordination, guest messaging, and maintenance dispatch.

A typical AirCover claim, start to finish, consumes one to two hours of ops coordinator time. That figure comes from our conversations with operators running 50 to 300 units; it matches the time estimates published by [The Host Report](https://www.thehostreport.com/articles/aircover-fine-print-what-every-airbnb-host-needs-to-know) and aligns with the documented claim process in the [Airbnb AirCover step-by-step guide](https://rapideyeinspections.com/blog/airbnb-aircover-damage-claim-guide/). Here is where the time goes on an average-complexity claim:

That is 90 minutes and $67.50 regardless of whether you recover $0 or $2,000. Complex claims with guest disputes or appeal processes can run to 3 or 4 hours. The $45 per hour rate is a fully loaded cost for a typical ops coordinator at a mid-sized STR management company, including benefits and overhead. Use your own number if you have one.

## 02 / Break-even mathThe filing threshold formula

The threshold question reduces to a single expected-value calculation. You file if expected net recovery is positive, skip if negative:

The 56.75 percent recovery rate comes from [Avada Properties' analysis of 20,000-plus bookings](https://avadaproperties.com/airbnb-vrbo-damage-claims-statistics-and-assumptions/), the only publicly available dataset on actual AirCover recovery ratios. Your operation may run higher or lower. Well-documented operations with tight baseline photography typically recover 65 to 75 percent. Operations that file reactively without baseline documentation run closer to 40 percent. Substitute your own recovery rate into the formula if you track it.

The resulting threshold at typical industry inputs lands at roughly $118. The $150 to $250 range we recommend in the header adds safety margin for inputs we cannot cleanly predict: claims that take longer than expected to resolve, adjuster follow-ups that drag into additional ops hours, and partial denials that reduce the realized recovery rate below 57 percent. Above $250, the math is clearly positive on every reasonable input. Below $150, the math is clearly negative.

## 03 / Scenario tableWhat the math looks like at real claim amounts

Here is the break-even calculation run across eight realistic claim amounts, using the baseline inputs (1.5 hours at $45, 57 percent recovery). Green rows are net-positive and clearly worth filing. Red rows are net-negative. Yellow rows are marginal and depend on the specifics.

| Scenario | Claimed | Expected recovery | Ops cost | Net | File? |
| --- | --- | --- | --- | --- | --- |
| Stained sheet set | $60 | $34 | $67 | −$33 | Skip |
| Broken lamp, scuffed wall | $120 | $68 | $67 | +$1 | Skip |
| Damaged bath towels + decor | $180 | $102 | $67 | +$35 | Judgment |
| Cracked TV, 2 years old | $380 | $216 | $67 | +$149 | File |
| Burn mark on mattress | $650 | $369 | $67 | +$302 | File |
| Upholstered sofa damage | $1,200 | $681 | $67 | +$614 | File |
| Multi-item guest party damage | $2,500 | $1,419 | $135 | +$1,284 | File |
| Major water damage | $8,000 | $4,540 | $270 | +$4,270 | File |

Two things jump out of the table. First, **small claims are genuinely net-negative or break-even**, even though filing feels like free money. The $120 broken-lamp scenario recovers $68 against $67 in ops labor. You "earned" a dollar for an hour and a half of coordinator time. Second, **the payoff curve is steep above $500**. Once a claim clears the threshold, every additional dollar flows through at the recovery rate, and the ops cost stays roughly constant. Claims over $1,000 are where your ops labor budget actually generates positive margin.

**Ops cost of an average Airbnb damage claim.** Combined with the 57 percent recovery rate, this creates a hard floor on the claim size that makes financial sense to file. Below $150, the math says replace the item and move on.

## 04 / Adjust for your operationWhen to use a different threshold

The $150 to $250 threshold is the starting point. Three factors should move your number up or down:

### Your recovery rate

If your ops team consistently documents baseline photos, itemizes labor, and follows up on adjuster questions, your recovery rate is probably closer to 70 percent. At that rate, the break-even drops to $96, and your filing threshold can drop to $125 or $150. If you file claims reactively without baseline documentation, your recovery is closer to 40 percent and your threshold should rise to $200 or $300.

### Your ops labor cost

A solo operator handling claims personally has an opportunity cost, not a labor cost. Their effective rate is whatever else they could be doing with that 90 minutes. For a founder whose time is worth $100 per hour in revenue-generating work, the threshold jumps to $264. For a dedicated claims coordinator at a $28 fully loaded rate, the threshold drops to $74.

### Your portfolio size

At 10 units, you are filing maybe 2 to 3 claims per year. The absolute ops hours involved are rounding error and the threshold can be set lower simply because the aggregate cost does not materially impact the operation. At 200 units and 14 claims per year at the 0.71 percent frequency rate, ops labor adds up fast. A $150 threshold at 200 units saves roughly 10 hours of coordinator time per year compared to filing everything.

## 05 / ExceptionsWhen to file below the threshold anyway

The math is a starting point, not a rule. Four situations justify filing a below-threshold claim regardless of the break-even calculation:

## 06 / Policy templateFiling threshold policy for your ops team

Once you have the threshold, write it down. The most common failure mode at scale is not the threshold being wrong, it is that different coordinators file different claims based on personal judgment and the policy drifts. Here is a template policy you can adapt and drop into your ops playbook.

## 07 / Next stepUnderstand what actually drives the recovery rate

The threshold math assumes a 57 percent recovery rate because that is the industry average. If your operation is running below that number, the filing threshold shifts higher and smaller claims become even less worthwhile. The fastest way to improve the math is to push your recovery rate up, which means understanding *why* Airbnb pays out the percentages it does.

That logic lives in our companion piece on [how Airbnb actually calculates damage payouts](https://rapideyeinspections.com/blog/how-much-does-airbnb-pay-damage-claims/), including the depreciation formula, the industry-standard rates adjusters use, and the four categories of deductions that account for the 43 percent average gap between claimed and paid amounts. If you want to get your recovery rate to 70 percent, the answer is in that page.

#### When the math says go

- Claimed damage clearly above $250

- Guest has pattern of prior damage

- Policy violation worth documenting

- Critical-path item blocking rebooking

- You have clean baseline photos of the item

#### When the math says no

- Claimed damage clearly below $150

- Linens, low-cost soft goods, consumables

- Item over 8 years old (near the 90% depreciation floor)

- No baseline photo, no documentation trail

- Would require 3+ hours of ops follow-up

### The rest of the series

## FAQCommon questions

For most multi-unit property managers, the break-even threshold lands between $150 and $250 in claimed damage. Below that amount, the ops labor cost to document, file, and follow up on the claim typically exceeds the expected net recovery, given the 56.75 percent average Airbnb recovery rate.

A typical claim consumes one to two hours of ops coordinator time: 20 to 30 minutes documenting, 15 to 20 minutes filing, 20 to 40 minutes on adjuster follow-ups, and 10 to 20 minutes on payout reconciliation. At a $45 fully loaded hourly rate, that is $45 to $90 of ops cost per claim regardless of outcome.

At scale, no. A $100 claim recovers $57 against $45 to $90 in ops labor. The net is between negative $33 and positive $12, which is rarely worth the team time. Operators running 100-plus units should set their filing threshold at or above $150.

Four cases: guest has pattern of damage across multiple stays, damage documents a policy violation relevant to future disputes, item is on the property's critical-path replacement list, or filing serves as a signal to the guest. In these situations, the claim value goes beyond immediate dollar recovery.

Use the formula: filing threshold equals ops hours per claim times hourly rate divided by recovery rate. For 1.5 hours at $45 against a 57 percent recovery, break-even is $118. Round up to $150 for margin. Document the threshold in your ops playbook so coordinators understand why the number is what it is.

### Sources & Primary References

- Avada Properties. [Airbnb and Vrbo Damage Claims Statistics and Assumptions](https://avadaproperties.com/airbnb-vrbo-damage-claims-statistics-and-assumptions/). Analysis of 20,000+ Smoky Mountain bookings showing 56.75% Airbnb recovery and 0.71% claim frequency.
 https://avadaproperties.com/airbnb-vrbo-damage-claims-statistics-and-assumptions/

- Airbnb. [Host Damage Protection Terms](https://www.airbnb.com/help/article/2869). Defines the 14-day filing window, Actual Cash Value calculation, and Resolution Center claim workflow.
 https://www.airbnb.com/help/article/2869

- The Host Report. [AirCover Fine Print: What Every Airbnb Host Needs to Know](https://www.thehostreport.com/articles/aircover-fine-print-what-every-airbnb-host-needs-to-know). Operator perspective on AirCover claim lifecycle and typical time investment.
 https://www.thehostreport.com/articles/aircover-fine-print-what-every-airbnb-host-needs-to-know

- ClaimsPages.com. [Property Depreciation Calculators](https://www.claimspages.com/tools/depreciation/). The industry-standard annual depreciation rates referenced throughout our companion piece on AirCover payouts.
 https://www.claimspages.com/tools/depreciation/