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
4.81 out of 5 average rating, 132 reviewsWaterview from three sides, Cabana Club, 30' Docks
3–10 Aug
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
27 Feb – 6 Mar
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
14–21 Dec
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 Nov
Home in Marathon
4.97 out of 5 average rating, 36 reviewsWaterfront Private Home w/Pool-Family&Pet Friendly
6–13 Oct
Home in Duck Key
5.0 out of 5 average rating, 31 reviewsPrivate Pool Tropical Oasis - Centrally Located
20–27 Nov
Home in Marathon
4.98 out of 5 average rating, 84 reviewsAnglers Terrace, Condé Nast Traveler's Best Airbnb
6–13 Jul
Condo rentals with a pool
Condo in Tavernier
4.88 out of 5 average rating, 229 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
26 Sep – 3 Oct
Condo in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
18–25 Sep
Condo in Tavernier
4.99 out of 5 average rating, 102 reviewsOcean View Corner Penthouse | Ocean Pointe 5416
24–31 Aug
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
22–29 Aug
Condo in Fort Lauderdale
4.93 out of 5 average rating, 264 reviews*Marriott's BeachPlace Towers Luxury Guest Room Sl
30 Sep – 7 Oct
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
25 Apr – 2 May
Condo in Tavernier
4.93 out of 5 average rating, 134 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
19–26 Dec
Condo in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
24–31 Oct
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 Fort Lauderdale
4.63 out of 5 average rating, 32 reviewsMid Century Modern Pool Home In the Best Location!
17–24 Apr
Home in Wilton Manors
4.64 out of 5 average rating, 14 reviewsTowering Palms, Wilton Manors - Heated Pool & Spa
22–29 Sep
Home in Marco Island
4.83 out of 5 average rating, 6 reviewsSandcastle of Marco Island Waterfront Private Pool
5–12 Mar
Home in Wilton Manors
4.43 out of 5 average rating, 7 reviewsShangri-La
29 Sep – 6 Oct
Villa in Fort Lauderdale
Casa Lago
15–22 May
Home in Fort Lauderdale
A Snow Fort Iii - Poinsettia Heights Gem
9–16 Nov
Home in Fort Lauderdale
4.38 out of 5 average rating, 13 reviewsParadise W/ Private Pool! Close to Everything!
20–27 Oct
Destinations to explore
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