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
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 Cudjoe Key
4.97 out of 5 average rating, 121 reviewsCudjoe Key Home with a View
Oct 7 – 14
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Dec 14 – 21
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
Feb 13 – 20
Home in Marathon
5.0 out of 5 average rating, 17 reviewsGrouper Getaway @ Ocean Isles Fishing Village
May 8 – 15
Home in Cudjoe Key
4.86 out of 5 average rating, 43 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Oct 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
Apr 12 – 19
Home in Marathon
4.97 out of 5 average rating, 36 reviewsWaterfront Private Home w/Pool-Family&Pet Friendly
Nov 10 – 17
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 North Bay Village
4.86 out of 5 average rating, 236 reviewsGorgeous studio with water & downtown view.
Aug 22 – 29
Condo in Tavernier
4.88 out of 5 average rating, 228 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Aug 27 – Sep 3
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
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
Nov 8 – 15
Condo in Tavernier
4.93 out of 5 average rating, 133 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
Feb 14 – 21
Condo in Tavernier
4.99 out of 5 average rating, 101 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
Jan 12 – 19
Condo in Tavernier
4.97 out of 5 average rating, 158 reviewsSerenity In The Sun
Mar 23 – 30
Home rentals with a private pool
Home in Marco Island
4.83 out of 5 average rating, 6 reviewsLighthouse 1124
Apr 21 – 28
Home in Marco Island
4.83 out of 5 average rating, 6 reviewsSandcastle of Marco Island Waterfront Private Pool
Mar 1 – 8
Condo in Miami
Fontainebleau Sorrento Tower Private Pool View
Aug 1 – 8
Villa in Fort Lauderdale
Casa Lago
May 31 – Jun 7
Condo in Hollywood
Resort Condo Stunning White Sand Beaches
Aug 14 – 21
Condo in Hallandale Beach
Private Luxury Ocean View Condo Resort Lifestyle
Jun 5 – 12
Condo in Hollywood
Modern Condo Private Balcony and Resort Luxuries
Nov 7 – 14
Condo in Sunny Isles Beach
Luxury Beach Suite In a 4 Star Family Resort
Mar 24 – 31
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