AirROI ranking · 202660 companies ranked
Vacation Rental and Airbnb Management Companies in the Florida Keys (2026)
The vacation rental and Airbnb management companies across Marathon, Key Largo, Islamorada, Tavernier, Key Colony Beach, Big Pine Key, Cudjoe Key, Duck Key, Key West, Stock Island, and Summerland Key, ranked by the homes they run there. AirROI counts 140 active Airbnb homes run by Vacation Rentals Of The Fla in the Florida Keys, the most of any management company (12 months to October 2026). AirROI rates KeysCations Vacation Rentals the best-rated among Florida Keys companies with 25+ homes and 500+ reviews, at 4.94 over 580 reviews. No company runs more than 2.9% of the Florida Keys' Airbnb listings, and the ten largest together run 18%.
Updated monthly. Airbnb homes live at least 3 months in the 12 months to October 2026, each counted once; companies with fewer than 5 are not counted, so every count is a floor. Market data: Florida Keys Airbnb market.
- Ranked companies running 10+ listings
- 48
- Active Airbnb listings
- 4,802
- Listings run by companies
- 40%
Ranking
Who Are the Best Airbnb Management Companies in the Florida Keys?
By active Airbnb listings, the largest Airbnb management companies in the Florida Keys are Vacation Rentals Of The Fla (140), Casago (127), and Brightwild (108). By guest rating, KeysCations Vacation Rentals ranks first at 4.94 over 580 reviews, ahead of Last (4.91) and Historic Key West Vacation Rentals (4.90). The table ranks the 60 largest; switch the order to see the best rated and the most listings added.
Largest Airbnb management companies in Florida Keys
Ranked by active Airbnb homes run as host or co-host in Florida Keys; "All markets" is the company's homes everywhere and the markets they sit in.
| # | Company | In Florida Keys |
|---|---|---|
| Vacation Rentals Of The Fla, Marathon, Key Colony Beach, Duck Key · ★ 4.76, 6 markets · +25 in a year | 140 | |
| Casago, Key West, Marathon, Key Colony Beach, 585 markets · +41 in a year | 127 | |
| Brightwild, Key West, Stock Island, Summerland Key, 12 markets | 108 | |
| 4 | Florida Stays, Islamorada, Key West, Tavernier, 31 markets · +13 in a year | 95 |
| 5 | Rent Key West Hideaways, Key West, Big Pine Key · ★ 4.80, 2 markets | 83 |
| 6 | Last, Key West, Cudjoe Key, Stock Island · ★ 4.91, 4 markets | 75 |
| 7 | Colocada Vacation Rentals, Key West · ★ 4.82, 1 market · +10 in a year | 62 |
| 8 | Bluescape, Cudjoe Key, Summerland Key, Big Pine Key · ★ 4.78, 5 markets · +32 in a year | 60 |
| 9 | RoomPicks, Key West, Islamorada, Marathon, 353 markets · +32 in a year | 59 |
| 10 | BHHS Keys Vacation Rentals, Key West, Big Pine Key, Cudjoe Key · ★ 4.86, 9 markets | 50 |
| 11 | Vacasa, Marathon, Key Colony Beach, Key West, 815 markets | 49 |
| 12 | AvantStay, Key West, Stock Island · ★ 4.78, 218 markets | 42 |
| 13 | Largo, Tavernier, Islamorada · ★ 4.89, 2 markets | 39 |
| 14 | Barefeet Vacation, Key Largo, Tavernier · ★ 4.77, 2 markets | 38 |
| 15 | Historic Key West Vacation Rentals, Key West · ★ 4.90, 1 market | 36 |
| 16 | Rent Key West Vacations, Key West · ★ 4.79, 1 market | 35 |
| 17 | First Class Stays, Islamorada, 6 markets | 31 |
| 18 | iTrip, Marathon, Key West, Summerland Key · ★ 4.73, 275 markets | 30 |
| 19 | Island Breeze, Marathon, Key Colony Beach, Key Largo · ★ 4.74, 3 markets | 29 |
| 20 | The Key To The Keys Vacation Rentals, Marathon, Key Largo, Key Colony Beach · ★ 4.88, 3 markets | 29 |
| 21 | Kees, Key West, 1 market | 28 |
| 22 | KeysCations Vacation Rentals, Marathon, Key Colony Beach · ★ 4.94, 2 markets | 26 |
| 23 | Old Wooden Bridge, Big Pine Key, 1 market | 26 |
| 24 | Ocean Sunrise Vacation Rentals, Key Largo, Islamorada, Tavernier · ★ 4.89, 4 markets | 22 |
| 25 | Paraiso Vacation Rentals, Marathon, Key Colony Beach · ★ 4.91, 3 markets | 18 |
| 26 | Keys 2 Joy, Key Colony Beach, Marathon · ★ 4.80, 2 markets | 18 |
| 27 | KeysTime Vacation Rentals, Key West, Marathon · ★ 4.90, 2 markets | 17 |
| 28 | Kaleigh, Marathon, Key Colony Beach, 2 markets | 15 |
| 29 | Keys Ocean Vacation Rentals, Marathon, Key Colony Beach, Islamorada, 4 markets | 15 |
| 30 | Star Properties, Key Largo, Marathon, Tavernier, 5 markets | 15 |
| 31 | Evolve, Marathon, Key Largo, Key Colony Beach · ★ 4.77, 4,689 markets | 14 |
| 32 | Tesi, Marathon, Key Colony Beach · ★ 4.87, 3 markets | 14 |
| 33 | Newman Hospitality, Islamorada, Key Largo · ★ 4.94, 18 markets | 13 |
| 34 | Elite Alliance Hospitality, Marathon, 4 markets | 13 |
| 35 | Bodil, Marathon, Key Largo, Duck Key · ★ 4.75, 3 markets | 12 |
| 36 | Jossie, Key Largo · ★ 4.77, 1 market | 12 |
| 37 | Kwvpr, Key West, 1 market | 12 |
| 38 | Magen, Key West · ★ 4.93, 1 market | 12 |
| 39 | Marreros, Key West · ★ 4.94, 1 market | 12 |
| 40 | Waterfront Keys, Cudjoe Key, 1 market | 12 |
| 41 | Martin, Key Largo · ★ 4.78, 185 markets | 11 |
| 42 | Leavetown Vacations, Duck Key, Islamorada · ★ 4.73, 278 markets | 11 |
| 43 | PRO VRO Vacation Rentals, Marathon, Key Colony Beach · ★ 4.94, 2 markets | 11 |
| 44 | Roompicks By Victoria, Key Largo, Marathon · ★ 4.83, 74 markets | 10 |
| 45 | Largo, Key Largo · ★ 4.79, 1 market | 10 |
| 46 | Micheal, Key West, Cudjoe Key, Stock Island · ★ 4.78, 3 markets | 10 |
| 47 | Keezy Vacation, Cudjoe Key · ★ 4.91, 1 market | 9 |
| 48 | Chris, Key West, 37 markets | 8 |
| 49 | Dolphin Point Villas, Key Largo · ★ 4.77, 1 market | 8 |
| 50 | Infinity Keys Property Management, Cudjoe Key, Marathon, 2 markets | 8 |
| 51 | Latitude Key, Islamorada, 8 markets | 7 |
| 52 | Life In Paradise, Key Largo · ★ 4.91, 2 markets | 7 |
| 53 | Keys Holiday, Islamorada, 1 market | 7 |
| 54 | C’est La Vie, Key Largo · ★ 4.86, 7 markets | 6 |
| 55 | Rveedom, Stock Island, Key West · ★ 4.76, 6 markets | 6 |
| 56 | Walkabout Retreat, Cudjoe Key, Summerland Key, 3 markets | 6 |
| 57 | Subhodeep, Key West · ★ 4.95, 95 markets | 5 |
| 58 | Emperor Rentals, Marathon, Key Colony Beach, 30 markets | 5 |
| 59 | Chimera, Key West, 10 markets | 5 |
| 60 | Dolphin Vacations, Marathon, Key West, 2 markets | 5 |
Best-rated Airbnb management companies in Florida Keys
Average guest rating across each company's rated listings, weighted by reviews, among companies with 25 or more listings and 500 or more reviews.
| # | Company | Average rating |
|---|---|---|
| KeysCations Vacation Rentals, Marathon, 580 reviews | 4.94 | |
| Last, Key West, 1,906 reviews | 4.91 | |
| Historic Key West Vacation Rentals, Key West, 862 reviews | 4.90 | |
| 4 | Largo, Tavernier, 2,924 reviews | 4.89 |
| 5 | The Key To The Keys Vacation Rentals, Marathon, 894 reviews | 4.88 |
| 6 | BHHS Keys Vacation Rentals, Key West, 1,756 reviews | 4.86 |
| 7 | Colocada Vacation Rentals, Key West, 939 reviews | 4.82 |
| 8 | Rent Key West Hideaways, Key West, 4,548 reviews | 4.80 |
| 9 | Rent Key West Vacations, Key West, 3,224 reviews | 4.79 |
| 10 | AvantStay, Key West, 1,045 reviews | 4.78 |
| 11 | Vacation Rentals Of The Fla, Marathon, 2,016 reviews | 4.76 |
Airbnb management companies adding the most listings in Florida Keys
Listings added over the past 12 months on each company's own Airbnb accounts, among companies running 25 or more today.
| # | Company | Listings added |
|---|---|---|
| Casago, Key West, Marathon, Key Colony Beach, 585 markets | +41 | |
| Bluescape, Cudjoe Key, Summerland Key, Big Pine Key · ★ 4.78, 5 markets | +32 | |
| RoomPicks, Key West, Islamorada, Marathon, 353 markets | +32 | |
| 4 | Vacation Rentals Of The Fla, Marathon, Key Colony Beach, Duck Key · ★ 4.76, 6 markets | +25 |
| 5 | Florida Stays, Islamorada, Key West, Tavernier, 31 markets | +13 |
| 6 | Colocada Vacation Rentals, Key West · ★ 4.82, 1 market | +10 |
How to read this table
Largest individual hosts in the Florida Keys
| # | Host | In the Florida Keys |
|---|---|---|
| 1 | Leslie | 76 |
| 2 | Coco Plum | 73 |
| 3 | Julia | 51 |
| 4 | Lisa | 45 |
| 5 | Sean | 44 |
| 6 | Kim | 26 |
| 7 | Julia | 23 |
| 8 | Kata | 21 |
| 9 | Frank | 18 |
| 10 | Javier | 18 |
| 11 | Jessica | 18 |
| 12 | Vivian | 18 |
| 13 | Jenny | 17 |
| 14 | Aneta | 16 |
| 15 | Frank | 16 |
| 16 | Norman | 16 |
| 17 | Shawn | 16 |
| 18 | Cindy | 15 |
| 19 | John Carl | 15 |
| 20 | Julia | 15 |
| 21 | Lindsey | 15 |
| 22 | John | 14 |
| 23 | Allison | 14 |
| 24 | Jacqueline | 14 |
| 25 | Katie | 14 |
Accounts under a person's name running 10 or more homes. They are not management companies, so they are not ranked above and have no profile.
Download the ranking as a CSV file, with each company's listings, markets, rating and growth.
Where
Where in the Florida Keys Do Management Companies Run the Most Homes?
In the Florida Keys, companies run the most Airbnb listings in Key West, Marathon, and Key Largo. Each city below links to its Airbnb market data.
Companies run the most homes in Key West, Marathon, and Key Largo
Listings run by companies as host or co-host, 12 months to October 2026. Numbered pins match the rows.
| # | City | Share of listings | |
|---|---|---|---|
| Key West | 720 | 57% | |
| Marathon | 404 | 36% | |
| Key Largo | 178 | 20% | |
| 4 | Islamorada | 140 | 38% |
| 5 | Cudjoe Key | 100 | 51% |
| 6 | Key Colony Beach | 88 | 30% |
Fees
How Much Does an Airbnb Manager Charge in the Florida Keys?
AirROI does not publish or estimate any single company's fee, so ask for the rate card in writing. AirROI has not checked fees for any Florida Keys company, so these figures pool the 81 companies it checked in 6 US cities: 49 quote only on request, and the 9 that publish a rate charge 10% to 30% of booking revenue.
- Median starting fee, US
- 15%
- Published fee range
- 10%–30%
- Quote only on request
- 49 of 81
In Key West, the average Airbnb earned $97,100 over the 12 months to October 2026. A 15% fee on that is about $14,600 a year.
The fee a year on the average Airbnb in Key West
- At 15%
- $14,600
- At 20%
- $19,400
- At 25%
- $24,300
- At 30%
- $29,100
AirROI compares company-run and owner-run homes in the cities it has management pages for, none of them in the Florida Keys. See whether an Airbnb manager is worth it in Florida.
Before you sign
What Should You Ask Before You Sign?
Market
How Many Airbnb Management Companies Are There in the Florida Keys?
48 companies that manage homes for owners run 10 or more active Airbnb listings in the Florida Keys, and 62 run 5 or more, in AirROI's data for the 12 months to October 2026. Hosts with no business account run 60% of all listings.
The ten largest companies run 18% of Airbnb listings in the Florida Keys, and the largest runs 2.9%
Share of 4,802 active Airbnb listings by who runs them, 12 months to October 2026
- The largest company 2.9%
- The next nine largest 15%
- Other companies and business accounts 22%
- Hosts with no business account 60%
Questions
Questions About Airbnb Management in the Florida Keys
Who Is the Best Airbnb Management Company in the Florida Keys?
AirROI counts 140 active Airbnb homes run by Vacation Rentals Of The Fla in the Florida Keys, the most of any management company (12 months to October 2026). AirROI rates KeysCations Vacation Rentals the best-rated management company in the Florida Keys, at 4.94 over 580 guest reviews (12 months to October 2026). No single measure makes a company best for your home: check that it runs homes like yours, in your area, before you sign.
Which Vacation Rental Companies Have the Most Homes in the Florida Keys?
Vacation Rentals Of The Fla runs 140 active homes on Airbnb in the Florida Keys in the 12 months to October 2026, ahead of Casago (127) and Brightwild (108). A company that sells most of its calendar on Vrbo or its own site can show fewer homes here than it runs.
Why Does a Company Show Fewer Homes Here Than on Airbnb?
This page counts a home only when it was live in at least 3 of the 12 months, live in at least 1 of the last 3, and had 3 or more booked or blocked nights in its live months, and only in the Florida Keys. A company's Airbnb profile shows every listing it has ever published, including homes that have not opened yet, homes listed for a few weeks, and homes elsewhere. Open a row for the company's homes in its other markets, or its profile for every home tied to it and why each one is or is not counted.
Why Is a Company Ranked Differently in a Town and in Its Region?
Each page ranks companies by their homes in that place alone. A company with a few homes in one town and more in the towns around it ranks lower on the town's page than on the region or state page, where every town's homes count. The "All markets" column gives the company's homes everywhere, so the two rankings can be read together.
Method
About This Data
- Listings
- Active Airbnb listings over the 12 months to October 2026: open to bookings through the year, each counted once per company for its host and for every co-host. Airbnb only: homes listed only on Vrbo, Booking.com or a company's own site are not counted.
- Companies
- A company's Airbnb accounts with 5 or more active listings are joined into one company, so counts and shares are floors. Companies that manage homes for owners are ranked; hotels, resorts and booking platforms are counted in the totals but not ranked.
- Ratings
- Airbnb's guest rating, averaged across a company's listings and weighted by their reviews. Shown from 4.7 over 100 or more reviews; the best-rated order needs 25+ listings and 500+ reviews.
- Growth
- Listings added on a company's own Airbnb accounts over 12 months, for companies that ran 10 or more a year ago. Co-hosted listings from a year ago are not fully recorded, and a takeover or a rename shows as growth.
- Fees
- Published owner terms on company websites, checked September 29, 2026, pooled across the companies checked. No company's fee is shown.
- Independence
- No company can pay to be listed or ranked, and nothing is self-reported. The ranking is updated every month; this edition on November 4, 2026, the next in December 2026.