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, 195 reviewsNewly Renovated Oceanside House with Pool
Home in Marathon
4.95 out of 5 average rating, 118 reviewsParadise - Pool, Hot tub, Mini Golf, Dockage, Fish
Home in Marathon
4.98 out of 5 average rating, 122 reviewsMarathon one-level home on the Marina - with slip!
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
4.91 out of 5 average rating, 117 reviewsThe Snapper House 3/2.5 45' dock sleeps 8+ pets OK
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
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, 102 reviewsTropical Escape at Sunrise
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 Tavernier
4.95 out of 5 average rating, 110 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Condo in Marathon
4.88 out of 5 average rating, 200 reviewsSombrero Beach Tropical Getaway
Condo in Marathon
4.94 out of 5 average rating, 99 reviewsJune Discount! Marina, Pool, Tiki Bar, Waterside!
Condo in Tavernier
4.88 out of 5 average rating, 231 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Condo in Tavernier
4.96 out of 5 average rating, 163 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
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
$147 NZD before taxes and fees
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