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Featured Florida Keys Hotels with Pool

Southernmost Beach Resort
Southernmost Beach Resort
4.0 out of 5.0 1319 Duval Street, Key West, FL
Free Cancellation
$215
4.4/5 (329 reviews)

Loved it was close to small beach and had the pier on the property. Did not enjoy my balcony view of the parking lot, not what I was expecting. The shower was VERY small in my “superior” room and I’m only 5’2”.

Reviewed on Oct 13, 2019
Guests of Southernmost Beach Resort have access to a full-service spa, 3 outdoor pools, and a fitness center. Self parking is available for USD 30.10 per day. ...
PoolBeachBar
Silver Palms Inn
Silver Palms Inn
3.5 out of 5.0 830 Truman Ave, Key West, FL
Free Cancellation
$139
4.4/5 (132 reviews)

We stayed only one night but it was pleasant. The room was clean, the staff friendly and the hotel is like 5 to 8 minutes walk from the action. Will stay again for sure. Having breakfast is also a great plus.

Reviewed on Oct 4, 2019
At Silver Palms Inn, guests have access to an outdoor pool, free WiFi in public areas, and coffee in a common area. If you decide to drive, there's free parking. ...
PoolOutdoor PoolBiking
Amara Cay Resort
Amara Cay Resort
3.5 out of 5.0 80001 Overseas Hwy, Islamorada, FL
Free Cancellation
$165
4.2/5 (47 reviews)

Such a perfect spot in a sleepy town! Grounds were perfect

Reviewed on Oct 11, 2019
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a fitness center. You can take advantage of free parking, along with a free area shuttle. ...
PoolOutdoor PoolBar
Sheraton Suites Key West
Sheraton Suites Key West
3.5 out of 5.0 2001 S Roosevelt Blvd, Key West, FL
Free Cancellation
$165
4.2/5 (178 reviews)

This hotel gives you access to all of Key West without ever having to move your car. We did book this hotel last minute; so expectations were low, but we were pleasantly surprised. The resort fee included so much more than parking and a pool. We received smoothies just after lunch, virgin mojitos, ...

Reviewed on Jul 8, 2019
Guests staying at Sheraton Suites Key West enjoy an outdoor pool, a 24-hour fitness center, and a spa tub. You can take advantage of free parking, along with ...
PoolTransportation ServicesOutdoor Pool
24 North Hotel Key West
24 North Hotel Key West
4.0 out of 5.0 3820 North Roosevelt Boulevard, Key West, FL
Free Cancellation
$127
4.1/5 (97 reviews)

Good pool, great staff, easy parking. Convenient shuttle.

Reviewed on Aug 28, 2019
Built in 2015, the brand new 24 North Hotel Key West offers an outdoor pool, a fitness center, and free WiFi in public areas. You can take advantage of free ...
PoolTransportation ServicesOutdoor Pool
Best Western Key Ambassador Resort Inn
Best Western Key Ambassador Resort Inn
2.5 out of 5.0 3755 S Roosevelt Blvd, Key West, FL
Free Cancellation
$139
4.1/5 (81 reviews)

Beautiful property- nice ocean and pool view from the room- comfortable bed- bar and pool on site. Close enough to downtown

Reviewed on Jun 25, 2019
Best Western Key Ambassador Resort Inn features an outdoor pool, free WiFi in public areas, and a 24-hour business center. There's free parking, as well as a ...
PoolOutdoor PoolBar
Parrot Key Hotel & Villas
Parrot Key Hotel & Villas
4.0 out of 5.0 2801 N Roosevelt Blvd, Key West, FL
Free Cancellation
$169
4.0/5 (195 reviews)

All the staff were wonderful and helpful. The location is good, minutes from downtown but away enough that it's quiet, across from a shopping center and next door to a Walgreen's if you need anything.

Reviewed on Aug 14, 2019
Guests staying at Parrot Key Hotel & Villas enjoy access to 4 outdoor pools, a fitness center, and free WiFi in public areas. Valet parking is available for ...
PoolSwimmingGardens
Fairfield Inn and Suites by Marriott Key West
Fairfield Inn and Suites by Marriott Key West
3.0 out of 5.0 2400 N Roosevelt Blvd, Key West, FL
Free Cancellation
$170
3.9/5 (141 reviews)

This property was truly more than I could have expected for the price. Wonderful pool with a bar, breakfast included, the hourly shuttle into town... all of it made for an incredible vacation.

Reviewed on Sep 10, 2019
At Fairfield Inn and Suites by Marriott Key West, guests enjoy an outdoor pool, a 24-hour fitness center, and free WiFi in public areas. There's free parking ...
PoolMicrowaveFree Parking
The Gates Hotel Key West
The Gates Hotel Key West
4.0 out of 5.0 3824 N Roosevelt Blvd, Key West, FL
Free Cancellation
$135
3.7/5 (96 reviews)

very nice, everything was great, clean and very confortable

Reviewed on Sep 30, 2019
Built in 2015, the brand new The Gates Hotel Key West offers an outdoor pool, a fitness center, and free WiFi in public areas. You can take advantage of free ...
PoolTransportation ServicesOutdoor Pool

Dive into These Florida Keys Hotels with Pools

Whether you're looking for a sunny spot to take the family for a refreshing dip, or just want to kick back by a chic rooftop pool with views of the city, Florida Keys hotels with pool amenities offer something for everyone.

Florida Keys hotels with indoor pools ensure you get your swim time without worrying about weather. You can still brag that you spent your vacation poolside—rain or shine. Many hotels even offer access to both indoor and outdoor pools, giving you the best of both worlds.

Fun features of Florida Keys hotels with pools
If you’re planning a family getaway, a pool provides the ideal place for the kids to burn off some energy. Many options have a resort feel, with water slides, splash pads, and poolside activities.

If you’re looking for a luxe getaway, check out the range of chic Florida Keys hotels offering trendy rooftop pools with stunning views and elegant cocktail bars.

Spas, saunas, and more
Imagine relaxing in a Jacuzzi for a spa experience, with warm water and soothing jets melting your stress away, before jumping in a sauna to loosen your tired muscles, and cooling down with a quick dip in the pool.

Keep up with your fitness routine doing laps in the morning, or just sit with your feet in the water while you watch the kids play. And of course, let’s not forget a romantic evening dip with your special someone. Whether it's reconnecting, rejuvenating, or reenergizing that’s on your mind, a hotel pool is a must for your Florida Keys vacation.


Recent Hotels with Pool Reviews

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.