Holiday rentals with a pool in Key West
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Key West
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 Key West rentals with a pool
House rentals with a pool
Home in Key Colony Beach
4.96 out of 5 average rating, 138 reviewsBeautiful open plan remodeled home in Key Colony
Home in Cudjoe Key
4.89 out of 5 average rating, 194 reviewsNewly Renovated Oceanside House with Pool
Home in Marathon
4.99 out of 5 average rating, 110 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Home in Key Colony Beach
4.81 out of 5 average rating, 134 reviewsWaterview from three sides, Cabana Club, 30' Docks
Home in Upper Sugarloaf Key
4.88 out of 5 average rating, 50 reviewsBungalows at Sugarloaf Beach - The Lighthouse
Home in Key West
5.0 out of 5 average rating, 8 reviewsKey West Lighthouse Suite
Home in Key Colony Beach
5.0 out of 5 average rating, 66 reviewsLa casa azul step 3 to a private pool
Home in Key Largo
5.0 out of 5 average rating, 55 reviewsThe Paradise 2
Apartment rentals with a pool
Apartment in Key West
4.91 out of 5 average rating, 101 reviewsTropical Escape at Sunrise
Apartment in Key West
4.83 out of 5 average rating, 247 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
Apartment in Marathon
4.87 out of 5 average rating, 199 reviewsSombrero Beach Tropical Getaway
Apartment in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
Apartment in Key Colony Beach
4.91 out of 5 average rating, 117 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Apartment in Tavernier
4.95 out of 5 average rating, 110 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Apartment in Tavernier
4.88 out of 5 average rating, 231 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Apartment in Key West
4.93 out of 5 average rating, 45 reviewsBright Condo in Paradise
Quick stats about holiday rentals with a pool in Key West
Total rentals
1.4K properties
Rentals with dedicated workspaces
710 properties have a dedicated workspace
Pet-friendly rentals
330 properties allow pets
Family-friendly rentals
930 properties are a good fit for families
Total number of reviews
34K reviews
Nightly prices starting at
€ 83 before taxes and fees
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