Vacation 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.
Vacation 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
4.92 out of 5 average rating, 145 reviewsParadise and Cudjoe Bay
Home in Marathon
4.99 out of 5 average rating, 111 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Home in Key Colony Beach
4.81 out of 5 average rating, 135 reviewsWaterview from three sides, Cabana Club, 30' Docks
Home in Key West
5.0 out of 5 average rating, 11 reviewsKey West Lighthouse Suite
Home in Upper Sugarloaf Key
4.88 out of 5 average rating, 50 reviewsBungalows at Sugarloaf Beach - The Lighthouse
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 Marathon
4.97 out of 5 average rating, 36 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Home in Key West
4.98 out of 5 average rating, 48 reviewsPuerta Coralina @ Old Town - Cottage Near Duval
Condo rentals with a 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 Marathon
4.88 out of 5 average rating, 201 reviewsSombrero Beach Tropical Getaway
Condo in Key Colony Beach
4.81 out of 5 average rating, 109 reviewsBeachside Unit 28 - Private Beach, Pool & Paradise
Condo in Marathon
4.94 out of 5 average rating, 99 reviewsJune Discount! Marina, Pool, Tiki Bar, Waterside!
Condo in Tavernier
4.96 out of 5 average rating, 164 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Condo in Tavernier
4.88 out of 5 average rating, 231 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Condo in Key Largo
4.98 out of 5 average rating, 120 reviewsOceanfront Condo w/Lake, Kayak, Paddleboard & Bike
Quick stats about vacation 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
$90 before taxes and fees
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