Vacation 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.
Vacation rentals for every style
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Popular amenities for Florida Keys rentals with a pool
House rentals with a pool
Home in Key Colony Beach
4.96 out of 5 average rating, 134 reviewsBeautiful open plan remodeled home in Key Colony
Oct 23 – 30
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Apr 26 – May 3
Home in Marathon
5.0 out of 5 average rating, 16 reviewsHorizon
Aug 31 – Sep 7
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
Mar 20 – 27
Home in Cudjoe Key
4.86 out of 5 average rating, 42 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Oct 10 – 17
Home in Marathon
4.97 out of 5 average rating, 36 reviewsWaterfront Private Home w/Pool-Family&Pet Friendly
Nov 10 – 17
Home in Key Colony Beach
5.0 out of 5 average rating, 65 reviews“La casa azul” step 3’ to a private pool
Jul 2 – 9
Home in Upper Sugarloaf Key
4.87 out of 5 average rating, 45 reviewsBungalows at Sugarloaf Beach - The Lighthouse
Feb 5 – 12
Condo rentals with a pool
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Aug 22 – 29
Condo in Tavernier
4.88 out of 5 average rating, 228 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Jan 12 – 19
Condo in North Bay Village
4.86 out of 5 average rating, 235 reviewsGorgeous studio with water & downtown view.
Aug 22 – 29
Condo in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
Jul 19 – 26
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Sep 29 – Oct 6
Condo in Tavernier
4.93 out of 5 average rating, 133 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
Dec 13 – 20
Condo in Key West
4.86 out of 5 average rating, 129 reviewsA Perfect Getaway
Dec 8 – 15
Condo in Tavernier
4.99 out of 5 average rating, 101 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
Dec 13 – 20
Home rentals with a private pool
Home in Marco Island
4.83 out of 5 average rating, 6 reviewsLighthouse 1124
Apr 19 – 26
Home in Marco Island
4.83 out of 5 average rating, 6 reviewsSandcastle of Marco Island Waterfront Private Pool
Nov 17 – 24
Condo in Miami
Fontainebleau Sorrento Tower Private Pool View
Jun 9 – 16
Villa in Fort Lauderdale
Casa Lago
Jun 20 – 27
Condo in Hollywood
Resort Condo Stunning White Sand Beaches
Nov 9 – 16
Condo in Hallandale Beach
Private Luxury Ocean View Condo Resort Lifestyle
Oct 7 – 14
Condo in Sunny Isles Beach
Luxury Beach Suite In a 4 Star Family Resort
Nov 12 – 19
Condo in Hollywood
Modern Condo Private Balcony and Resort Luxuries
Nov 3 – 10
Destinations to explore
- Miami Vacation rentals
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