Hotels with a Pool in Florida Keys

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
Apr 19 - Apr 20
Tomorrow
Apr 20 - Apr 21
Next weekend
Apr 25 - Apr 27
In two weeks
May 2 - May 4

Hotels with a Pool in Florida Keys

Parrot Key Hotel & Villas
Waterfront King Guest Room | Exterior

Parrot Key Hotel & Villas

4.0 star property
9.0 out of 10, Wonderful, (1009)
The price is $272
includes taxes & fees
$242 per night
May 19 - May 20
Parrot Key Hotel & Villas
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top neighborhoods in Florida Keys

Get a lay of the land and find the perfect place to stay
Restaurant with a pool to dip in on a hot day.

Key West Historic District

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

See properties in Key West Historic District
Key West Historic District

Top landmarks in Florida Keys

Duval Street featuring signage

Duval Street

If you want to give your credit card some exercise, head out to Duval Street, a popular place for shoppers in Key West Historic District. Splash some more cash at We Cycle Key West and Mallory Dock.

See properties in Duval Street
Duval Street

Frequently asked questions

What are the best hotels with a pool in Florida Keys?
Make a splash on your next getaway at a Florida Keys hotel with a pool. Visitors love Almond Tree Inn Hotel - Adults Only in Key West, which has an electric car charging station and pillow top mattresses as part of the stay too. Alternatively, stay at Bay Harbor Lodge in Key Largo, another top-rated option where you can chill by the pool.
What are the cheapest hotels with a pool in Florida Keys?
If Key West is on your itinerary, base yourself at Travelers Palm. Featuring a furnished patio and a garden, this is one of the best-priced stays with a pool here. Coconut Palm Inn is a top pick in Key Largo. Book a cheap hotel in Florida Keys with a pool from $132 and have more fun for less.
What is the best time to stay in a hotel with a pool in Florida Keys?
When deciding when to stay in a Florida Keys hotel with a pool, take into account timing. Peak season and other busy periods are exciting times to go. But they can also bring higher prices and crowded spaces. Think about your personal preferences, including whether you prefer lively peak times or quieter off-seasons.
What hotels with a pool are closest to Key West Intl. Airport (EYW)?
Hyatt Vacation Club at Windward Pointe, Key West is around 0.2 miles east of Key West Intl. Airport (EYW). A pool, a jetted bathtub and a barbecue grill are the start of the things you can take advantage of here. Another Florida Keys hotel with a pool near the airport is Hampton Inn Key West FL.
Are there any hotels with a pool in Florida Keys with parking?
Go for a swim while your car stays parked close to your room at Almond Tree Inn Hotel - Adults Only. This Key West stay features an electric car charging station and pillow top mattresses. Located in Key Largo, Bay Harbor Lodge combines poolside perks and parking convenience as well. You can take your pick of 8,326 Florida Keys hotels with a pool and a space for your ride.