Holiday rentals with a pool in Florida Keys
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Florida Keys
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Florida Keys rentals with a pool
House rentals with a pool
Home in Key Colony Beach
4.91 out of 5 average rating, 116 reviewsThe Snapper House 3/2.5 45' dock sleeps 8+ pets OK
Home in Cudjoe Key
4.89 out of 5 average rating, 194 reviewsNewly Renovated Oceanside House with Pool
Home in Marathon
5.0 out of 5 average rating, 18 reviewsHorizon
Home in Marathon
4.97 out of 5 average rating, 35 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Home in Marathon
4.98 out of 5 average rating, 85 reviewsAnglers Terrace, Condé Nast Traveler's Best Airbnb
Home in Key Colony Beach
5.0 out of 5 average rating, 65 reviewsLa casa azul step 3 to a private pool
Home in Marathon
5.0 out of 5 average rating, 4 reviewsP31 - 11785 5th Ave. Ocean
Home in Upper Sugarloaf Key
4.88 out of 5 average rating, 49 reviewsBungalows at Sugarloaf Beach - The Lighthouse
Apartment rentals with a pool
Apartment in Tavernier
4.88 out of 5 average rating, 229 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Apartment in Tavernier
4.96 out of 5 average rating, 161 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Apartment in Key Colony Beach
4.91 out of 5 average rating, 114 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Apartment in Tavernier
4.95 out of 5 average rating, 110 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Apartment in Tavernier
4.93 out of 5 average rating, 137 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
Apartment in Tavernier
4.98 out of 5 average rating, 145 reviewsOcean Views at Ocean Pointe
Apartment in Tavernier
4.99 out of 5 average rating, 103 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
Apartment in Tavernier
4.87 out of 5 average rating, 126 reviewsReel Large END Unit in Ocean Point Suites
Home rentals with a private pool
Home in Marco Island
4.83 out of 5 average rating, 6 reviewsLighthouse 1124
Home in Fort Lauderdale
4.63 out of 5 average rating, 32 reviewsMid Century Modern Pool Home In the Best Location!
Home in Marco Island
4.86 out of 5 average rating, 7 reviewsSandcastle of Marco Island Waterfront Private Pool
Home in Wilton Manors
4.67 out of 5 average rating, 15 reviewsTowering Palms, Wilton Manors - Heated Pool & Spa
Home in Dania Beach
New place to stayNew Listing! Private Villa with Pool and Sauna
Apartment in Miami
Fontainebleau Sorrento Tower Private Pool View
Home in Fort Lauderdale
A Snow Fort Iii - Poinsettia Heights Gem
Home in Fort Lauderdale
4.38 out of 5 average rating, 13 reviewsParadise W/ Private Pool! Close to Everything!
Destinations to explore
- Miami Holiday rentals
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