
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

Waterfront Home 37.5-ft dock, Cabana Club Included

Oct. Special 50% off! Oceanfront, 4 Bikes 2 Kayaks

Rise And Shine On The Water

Truman's Trove at The Annex

Marathon one-level home on the Marina - with slip!

Waterfront Sanctuary in the Keys!

Anglers Terrace, Condé Nast Traveler's Best Airbnb

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 3 bed condo Ocean Edge w/ optional slip

Keys Escape | Pool, Marina & Tiki Bar

Tropical Escape at Sunrise

EYW Getaway

Hyatt Beach House-Quiet Key West Spot!

Fully renovated 2/2 bath condo w/ shared pool!

Coral Palms 1BR/King/Queen, Pool, block to Duval
Other vacation rentals with a pool

Harvey's Haven Studio at the Hollinsed House

Keys to Ohana. Ocean views. Private Pool, Hot Tub

Newly Renovated 2/2 Bath Condo, with shared pool

Robinson Crusoe Cottage~ Delight In Island Vibes

The Palms

Henry's Penthouse On The Ocean

Waterfront Condo FREE Slip & Pool 2B2B in Key West

Private Pool! Luxury Paradise Pointe, Pet Friendly
Quick stats about vacation rentals with a pool in Key West
Total rentals
1.7K properties
Nightly prices starting at
€ 9 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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- Rentals with pools Monroe County
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