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 Marathon
4.97 out of 5 average rating, 119 reviewsMarathon one-level home on the Marina - with slip!
25 May – 1 Jun
Home in Cudjoe Key
4.89 out of 5 average rating, 193 reviewsNewly Renovated Oceanside House with Pool
26 Apr – 3 May
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
17–24 Aug
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
29 Mar – 5 Apr
Home in Marathon
5.0 out of 5 average rating, 17 reviewsHorizon
5–12 Apr
Home in Marathon
4.98 out of 5 average rating, 85 reviewsAnglers Terrace, Condé Nast Traveler's Best Airbnb
24–31 Aug
Home in Key Colony Beach
5.0 out of 5 average rating, 65 reviewsLa casa azul step 3 to a private pool
30 Nov – 7 Dec
Home in Duck Key
5.0 out of 5 average rating, 32 reviewsPrivate Pool Tropical Oasis - Centrally Located
10–17 Nov
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
27 Oct – 3 Nov
Apartment in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
28 Jan – 4 Feb
Apartment in Tavernier
4.99 out of 5 average rating, 102 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
6–13 Feb
Apartment in Tavernier
4.88 out of 5 average rating, 229 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
26 Sep – 3 Oct
Apartment in Fort Lauderdale
4.93 out of 5 average rating, 264 reviews*Marriott's BeachPlace Towers Luxury Guest Room Sl
30 Sep – 7 Oct
Apartment in Tavernier
4.93 out of 5 average rating, 136 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
30 Jan – 6 Feb
Apartment in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
26 Oct – 2 Nov
Apartment in Key West
4.86 out of 5 average rating, 130 reviewsA Perfect Getaway
7–14 Oct
Home rentals with a private pool
Home in Fort Lauderdale
5.0 out of 5 average rating, 10 reviewsCasa Sunset
20–27 Jun
Home in Marco Island
4.83 out of 5 average rating, 6 reviewsLighthouse 1124
20–27 Apr
Home in Fort Lauderdale
4.63 out of 5 average rating, 32 reviewsMid Century Modern Pool Home In the Best Location!
27 Dec – 3 Jan
Home in Marco Island
4.86 out of 5 average rating, 7 reviewsSandcastle of Marco Island Waterfront Private Pool
13–20 Aug
Home in Wilton Manors
4.64 out of 5 average rating, 14 reviewsTowering Palms, Wilton Manors - Heated Pool & Spa
23–30 Mar
Home in Fort Lauderdale
5.0 out of 5 average rating, 3 reviewsNew Listing! Lauderdale by the Sea
26 Feb – 5 Mar
Home in Dania Beach
New place to stayNew Listing! Private Villa with Pool and Sauna
29 Sep – 6 Oct
Home in Wilton Manors
4.43 out of 5 average rating, 7 reviewsShangri-La
9–16 Jul
Destinations to explore
- Miami Holiday rentals
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