
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

Waterfront Escape -VACA-23-408

Cancellation Deal: 08/02 thru 08/09

Cudjoe Key Home with a View

Waterfront Home 37.5-ft dock, Cabana Club Included

Beach House, Private Pool & Dock, Gulf Sunset view

Palm Breezes! Room for Everyone on the Ocean.

Private Pool! Luxury Paradise Pointe, Pet Friendly

Your clean and cosy family home in Key West
Condo rentals with a pool

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

Oceanfront Sunrise Condo Private Beach Heated Pool

Waterfront Getaway w/ Pool, Tiki Bar & Marina

Galleon Resort - Walk to Duval & Mallory Square!

Affordable Beachfront Luxury Condo Sleeps 6

The Palms

EYW Getaway

Waterfront 4-Bedroom 3-Bath Condo at Bayfront Suit
Quick stats about holiday rentals with a pool in Key West
Total rentals
1.7K properties
Nightly prices starting at
$15 AUD before taxes and fees
Total number of reviews
41K reviews
Family-friendly rentals
1.1K properties are a good fit for families
Pet-friendly rentals
540 properties allow pets
Rentals with dedicated workspaces
920 properties have a dedicated workspace
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