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 Cudjoe Key
4.89 out of 5 average rating, 196 reviewsNewly Renovated Oceanside House with Pool
Home in Marathon
4.99 out of 5 average rating, 111 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Home in Marathon
4.98 out of 5 average rating, 122 reviewsMarathon one-level home on the Marina - with slip!
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, 11 reviewsKey West Lighthouse Suite
Home in Key Colony Beach
5.0 out of 5 average rating, 67 reviews“La casa azul” step 3’ to a private pool
Home in Key West
4.9 out of 5 average rating, 88 reviewsMango Cottage, a charming Key West home ready for
Home in Marathon
4.97 out of 5 average rating, 36 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Condo rentals with a pool
Condo in Key Colony Beach
4.91 out of 5 average rating, 117 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Condo in Key West
4.91 out of 5 average rating, 103 reviewsTropical Escape at Sunrise
Condo in Tavernier
4.95 out of 5 average rating, 110 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Condo in Key West
4.83 out of 5 average rating, 247 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
Condo in Marathon
4.94 out of 5 average rating, 100 reviewsPool, Tiki Bar, Waterside, minutes from the beach!
Condo in Marathon
4.88 out of 5 average rating, 201 reviewsSombrero Beach Tropical Getaway
Condo in Tavernier
4.96 out of 5 average rating, 164 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Condo in Key West
4.99 out of 5 average rating, 83 reviews*2 Blocks to Duval, Private Deck, Pool, Parking*
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
$136 AUD before taxes and fees
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