Find Hotels with a Pool in Florida Keys
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Our top choices for Florida Keys hotels with a pool
Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Windward Pointe, Key WestKey West
9.4 out of 10, Exceptional, (1,198 reviews)
- Oceanfront relaxation awaits with heated pool sanctuary and hot tub retreat, mere steps from Key West's beautiful Smathers Beach.
$295 nightly
The price is $332
Aug 13 - Aug 14
Total with taxes and fees
9.4 out of 10, Exceptional, (1,153 reviews)
- Bask in tropical bliss with a dip in the outdoor pool and hot tub near Smathers Beach.
$307 nightly
The price is $346
Aug 16 - Aug 17
Total with taxes and fees
9.0 out of 10, Wonderful, (1,440 reviews)
- Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.
$178 nightly
The price is $200
Aug 11 - Aug 12
Total with taxes and fees
9.4 out of 10, Exceptional, (1,738 reviews)
- Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
$184 nightly
The price is $207
Aug 17 - Aug 18
Total with taxes and fees
9.4 out of 10, Exceptional, (1,483 reviews)
- Dive into coastal bliss with a splashy pool scene and beachfront perks for aquatic adventures.
$259 nightly
The price is $286
Jul 19 - Jul 20
Total with taxes and fees
9.2 out of 10, Wonderful, (1,003 reviews)
- Splash into relaxation with indoor and outdoor pools surrounded by plush loungers and umbrellas at this waterfront retreat.
$184 nightly
The price is $207
Jul 19 - Jul 20
Total with taxes and fees
8.8 out of 10, Excellent, (1,022 reviews)
- Pool paradise awaits with breathtaking bay views and a pristine private beach just steps away.
$130 nightly
The price is $147
Aug 2 - Aug 3
Total with taxes and fees
9.2 out of 10, Wonderful, (1,393 reviews)
- A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
$179 nightly
The price is $201
Aug 16 - Aug 17
Total with taxes and fees
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.
Hotels with pools and free breakfast in Florida Keys
9.4 out of 10, Exceptional, (1738)
$184 nightly
The price is $207
Aug 17 - Aug 18
Total with taxes and fees
4-star hotels with pools in Florida Keys
8.8 out of 10, Excellent, (1800)
$238 nightly
The price is $268
Aug 11 - Aug 12
Total with taxes and fees
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 Florida Keys Hotel Reviews
Chesapeake Beach Resort
8/10 Good
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