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, 142 reviewsParadise at Cudjoe Bay
Home in Marathon
4.99 out of 5 average rating, 108 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Home in Cudjoe Key
4.97 out of 5 average rating, 124 reviewsCudjoe Key Home with a View
Home in Marathon
4.98 out of 5 average rating, 120 reviewsMarathon one-level home on the Marina - with slip!
Home in Key West
5.0 out of 5 average rating, 6 reviewsKey West Lighthouse Suite
Home in Key Largo
5.0 out of 5 average rating, 51 reviewsThe Paradise 2
Home in Key West
5.0 out of 5 average rating, 41 reviewsGorgeous Romantic Private Villa, Steps from Duval!
Home in Marathon
4.97 out of 5 average rating, 33 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, 114 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Condo in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
Condo in Key West
4.83 out of 5 average rating, 243 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
Condo in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
Condo in Marathon
4.87 out of 5 average rating, 193 reviewsSombrero Beach Tropical Getaway
Condo in Tavernier
4.88 out of 5 average rating, 229 reviewsSPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Condo in Key West
4.84 out of 5 average rating, 44 reviewsOcean front 1BR/1BA Suite w/ kitchen & living rm
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
€ 84 before taxes and fees
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