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