Hotels with a Pool in Florida Keys

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Hotels with a Pool in Florida Keys

Chesapeake Beach Resort
Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1479)
$183 nightly
The price is $206
Aug 3 - Aug 4
Total includes taxes and fees
Chesapeake Beach Resort
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 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 $157 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 8,118 Florida Keys hotels with a pool and a space for your ride.
Are all taxes and fees included in the Florida Keys hotel prices shown on Hotels.com?
Hotels.com provide upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.