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 Marathon
4.97 out of 5 average rating, 117 reviewsMarathon one-level home on the Marina - with slip!
Jan 23 – 30
Home in Marathon
4.99 out of 5 average rating, 106 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Apr 5 – 12
Home in Key Colony Beach
4.96 out of 5 average rating, 134 reviewsBeautiful open plan remodeled home in Key Colony
Nov 5 – 12
Home in Cudjoe Key
4.97 out of 5 average rating, 119 reviewsCudjoe Key Home with a View
Sep 20 – 27
Home in Marathon
4.97 out of 5 average rating, 32 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Apr 19 – 26
Home in Marathon
5.0 out of 5 average rating, 10 reviewsMillion Dollar View
Dec 7 – 14
Home in Marathon
5.0 out of 5 average rating, 6 reviewsMermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!
May 5 – 12
Home in Key Largo
5.0 out of 5 average rating, 48 reviewsThe Paradise 2
Sep 17 – 24
Condo rentals with a pool
Condo in Tavernier
4.95 out of 5 average rating, 106 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Sep 12 – 19
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Aug 17 – 24
Condo in Tavernier
4.88 out of 5 average rating, 227 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Oct 31 – Nov 7
Condo in Hollywood
4.89 out of 5 average rating, 151 reviewsBeach view condo on Hollywood Beach
Sep 5 – 12
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Mar 21 – 28
Condo in Key West
4.86 out of 5 average rating, 129 reviewsA Perfect Getaway
Jul 3 – 10
Condo in Marco Island
4.93 out of 5 average rating, 188 reviewsMarco Island Beach Club 310 1 bed/1 bath Renovated
Aug 18 – 25
Condo in Tavernier
4.93 out of 5 average rating, 133 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
Feb 10 – 17
Home rentals with a private pool
Home in Fort Lauderdale
4.63 out of 5 average rating, 32 reviewsMid Century Modern Pool Home In the Best Location!
Dec 1 – 8
Home in Wilton Manors
4.64 out of 5 average rating, 14 reviewsTowering Palms, Wilton Manors - Heated Pool & Spa
Sep 13 – 20
Home in Marco Island
4.83 out of 5 average rating, 6 reviewsSandcastle of Marco Island Waterfront Private Pool
Jan 28 – Feb 4
Home in Wilton Manors
4.67 out of 5 average rating, 6 reviewsShangri-La
May 1 – 8
Villa in Fort Lauderdale
Casa Lago
May 12 – 17
Home in Fort Lauderdale
Luxurious Oasis In Fort Lauderdale's Heart
Apr 10 – 17
Home in Fort Lauderdale
A Snow Fort Iii - Poinsettia Heights Gem
Feb 10 – 17
Home in Fort Lauderdale
4.38 out of 5 average rating, 13 reviewsParadise W/ Private Pool! Close to Everything!
Mar 2 – 9
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