Find Hotels with Pool in Florida Keys
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Florida Keys Hotels with Pool
Tonight
21 Sept - 22 SeptTomorrow
22 Sept - 23 SeptThis weekend
25 Sept - 27 SeptNext weekend
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.
£145
includes taxes & fees
22 Sept - 23 Sept
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.
£118
includes taxes & fees
22 Sept - 23 Sept
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.
£134
includes taxes & fees
28 Sept - 29 Sept
4. Parrot Key Hotel & Villas
Parrot Key Hotel & VillasNorthside Resort
- Splash into paradise at four tropical pools with poolside dining and coastal shuttles.
£154
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.
£176
includes taxes & fees
5 Oct - 6 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.
£93
includes taxes & fees
23 Sept - 24 Sept
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.
£144
includes taxes & fees
30 Sept - 1 Oct
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.
£83
includes taxes & fees
22 Sept - 23 Sept
View all properties
Hotels with pools and free breakfast in Florida Keys
£144
includes taxes & fees
30 Sept - 1 Oct
£118
includes taxes & fees
22 Sept - 23 Sept
£154
includes taxes & fees
12 Oct - 13 Oct
£93
includes taxes & fees
23 Sept - 24 Sept
£134
includes taxes & fees
28 Sept - 29 Sept
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key WestKey West
£112
includes taxes & fees
27 Sept - 28 Sept
£109
includes taxes & fees
22 Sept - 23 Sept
£69
includes taxes & fees
28 Sept - 29 Sept
£134
includes taxes & fees
22 Sept - 23 Sept
4-star hotels with pools in Florida Keys
£214
includes taxes & fees
22 Sept - 23 Sept
Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West Resort and SpaKey West Historic District
£248
includes taxes & fees
5 Oct - 6 Oct
£247
includes taxes & fees
22 Sept - 23 Sept
£144
includes taxes & fees
30 Sept - 1 Oct
£134
includes taxes & fees
28 Sept - 29 Sept
£285
includes taxes & fees
22 Sept - 23 Sept
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key WestKey West
£112
includes taxes & fees
27 Sept - 28 Sept
Playa Largo Resort & Spa, Autograph Collection
Playa Largo Resort & Spa, Autograph CollectionRock Harbor
£262
includes taxes & fees
4 Oct - 5 Oct
£134
includes taxes & fees
22 Sept - 23 Sept
£154
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"