Find Hotels with a Pool in Florida Keys
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Check availability on Florida Keys Hotels with a Pool
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2 Oct - 4 OctOur top choices for Florida Keys hotels with a pool
1. Beachside Resort & Residences
Beachside Resort & ResidencesKey West
- Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
AED 321
AED 712 total
includes taxes & fees
22 Sep - 23 Sep
2. Silver Palms Inn & Historic Homes
Silver Palms Inn & Historic HomesOld Town Key West
- Pristine waters in the outdoor pool offer relaxation after exploring Key West's vibrant attractions.
AED 294
AED 579 total
includes taxes & fees
22 Sep - 23 Sep
3. Hilton Key West Resort & Marina
Hilton Key West Resort & MarinaStock Island
- Float above the Florida Keys in a waterfront paradise with 6 serene pools, a private marina, and breathtaking sunset views.
AED 389
AED 657 total
includes taxes & fees
28 Sep - 29 Sep
4. Parrot Key Hotel & Villas
Parrot Key Hotel & VillasNorthside Resort
- Splash into paradise at four tropical pools with poolside dining and coastal shuttles.
AED 485
AED 756 total
includes taxes & fees
12 Oct - 13 Oct
5. Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Windward Pointe, Key WestKey West
- Oceanfront relaxation awaits with heated pool sanctuary and hot tub retreat, mere steps from Key West's beautiful Smathers Beach.
AED 618
AED 861 total
includes taxes & fees
4 Oct - 5 Oct
6. The Southernmost Inn - Adults Only
The Southernmost Inn - Adults OnlyOld Town Key West
- Dive into azure bliss at this Key West adults-only retreat with two pristine pools, hot tub sanctuary, and poolside loungers.
AED 262
AED 459 total
includes taxes & fees
23 Sep - 24 Sep
7. Havana Cabana at Key West
Havana Cabana at Key WestNew Town
- Poolside paradise awaits with hot tub, dining, and bar service at this vibrant Key West oasis.
AED 422
AED 707 total
includes taxes & fees
23 Sep - 24 Sep
8. Douglas House - Adults Only
Douglas House - Adults OnlyOld Town Key West
- Tropical poolside sanctuary just steps from Duval Street offers a heated outdoor pool surrounded by lush gardens and privacy.
AED 375
AED 464 total
includes taxes & fees
24 Sep - 25 Sep
View all properties
Hotels with pools and free breakfast in Florida Keys
AED 422
AED 707 total
includes taxes & fees
23 Sep - 24 Sep
AED 294
AED 579 total
includes taxes & fees
22 Sep - 23 Sep
AED 485
AED 756 total
includes taxes & fees
12 Oct - 13 Oct
AED 262
AED 459 total
includes taxes & fees
23 Sep - 24 Sep
AED 389
AED 657 total
includes taxes & fees
28 Sep - 29 Sep
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key WestKey West
AED 379
AED 550 total
includes taxes & fees
27 Sep - 28 Sep
AED 372
AED 538 total
includes taxes & fees
22 Sep - 23 Sep
AED 300
AED 338 total
includes taxes & fees
28 Sep - 29 Sep
AED 403
AED 660 total
includes taxes & fees
22 Sep - 23 Sep
4-star hotels with pools in Florida Keys
AED 804
AED 1,052 total
includes taxes & fees
24 Sep - 25 Sep
Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West Resort and SpaKey West Historic District
AED 856
AED 1,219 total
includes taxes & fees
5 Oct - 6 Oct
AED 951
AED 1,215 total
includes taxes & fees
22 Sep - 23 Sep
AED 422
AED 707 total
includes taxes & fees
23 Sep - 24 Sep
AED 389
AED 657 total
includes taxes & fees
28 Sep - 29 Sep
AED 1,025
AED 1,401 total
includes taxes & fees
22 Sep - 23 Sep
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key WestKey West
AED 379
AED 550 total
includes taxes & fees
27 Sep - 28 Sep
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
AED 966
AED 1,289 total
includes taxes & fees
4 Oct - 5 Oct
AED 403
AED 660 total
includes taxes & fees
22 Sep - 23 Sep
AED 485
AED 756 total
includes taxes & fees
12 Oct - 13 Oct
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.
View all propertiesTop Florida Keys Hotel Reviews
Cheeca Lodge & Spa
10/10 Excellent
"Loved the room, quiet vibe, designated parking, the water front area, and staff. Nice surrounding area. You need a car if you want to go to Key West or nearby cities. If you want activity recommend planning ahead. We were celebrating wedding anniversary and this fit the bill. Loved it and would come back. Things to be mindful of. Yes there is a resort fee and the property holds a fee per day for Incidentals. Having the ability to know it was negotiable would have been better than finding out when I checked out. Adult pool only was nice and relaxing. The other pools were nice but very lively, if you want to chill the other pools may not be your thing. We wanted to go to a night club with dancing but there were none in this area near the resort. We went to Hog heaven, live music was great but not a night club. The Cheeca Lodge and Spa was wonderful!"
Chesapeake Beach Resort
10/10 Excellent
"Todo"
Lime Tree Bay Resort
10/10 Excellent
"Location, amenities, staff was amazing, breakfast was incredible."
Parmer's Resort
10/10 Excellent
"Wonderful experience! We could walk out of our room to enjoy the water. Nice amenities too! Kayaks and more available, excellent breakfast every morning, way better than the standard breakfast. We would definitely stay there again."
Islander Resort
10/10 Excellent
"The property was well maintained and clean. All staff were friendly and helpful. Amenities were nice. Very relaxing atmosphere"