Search for Cheap Deals onHotels with Pools in Florida Keys
You choose what matters — star rating, location, amenities.
We pick the perfect hotel, packed with all your must-haves.
Your hotel is revealed right after booking!
Featured Florida Keys Hotels with a Pool
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...
Silver Palms Inn & Historic Homes
830 Truman Ave Key West FL
Fully refundableReserve now, pay when you stay
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular ...
Compass Hotel by Margaritaville Key West
2400 N Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool ...
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton
1996 Overseas Highway Marathon FL
Fully refundableReserve now, pay when you stay
Book a stay at this spa resort in Marathon. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...
The Southernmost Inn - Adults Only
525 United Street Key West FL
Fully refundableReserve now, pay when you stay
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3852 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the pool ...
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 Hotels by Star Rating
- More Hotel Types
- Other Hotel Accommodations
- Popular Neighborhoods
- Nearby Cities
- Top Hotels
Hotels by Star Rating
More Hotel Options in Florida Keys
- Beach Hotels in Florida Keys
- Family Hotels in Florida Keys
- Apartment Hotels in Florida Keys
- Hotels with Free Parking in Florida Keys
- Romantic Hotels in Florida Keys
- Historic Hotels in Florida Keys
- Luxury Hotels in Florida Keys
- Hotels with Hot Tubs in Florida Keys
- Resorts & Hotels with Spas in Florida Keys
- Hotel Wedding Venues in Florida Keys
Other Options
Top Neighborhoods in Florida Keys
Cities near Florida Keys
- Key West Hotels (43.43 mi)
- Miami Beach Hotels (94.1 mi)
- Marathon Hotels (7.5 mi)
- Key Largo Hotels (49.6 mi)
- Islamorada Hotels (34.7 mi)
- Coral Gables Hotels (86.62 mi)
- Tavernier Hotels (43.22 mi)
- Miami Springs Hotels (89.28 mi)
- Cudjoe Key Hotels (22.74 mi)
- Homestead Hotels (63.08 mi)
- Key Colony Beach Hotels (10.6 mi)
- Summerland Key Hotels (19.73 mi)
- Key Biscayne Hotels (87.9 mi)
- Stock Island Hotels (39.39 mi)
- Big Pine Key Hotels (14.88 mi)
- Hialeah Hotels (89.84 mi)
- South Florida Hotels (112.04 mi)
- Gulf of Mexico Hotels (574.61 mi)
- Long Key Hotels (21.51 mi)
- Florida City Hotels (61.97 mi)
Most Booked Hotels in Florida Keys
- Cheeca Lodge & Spa
- Isla Bella Beach Resort & Spa
- Reefhouse Resort & Marina
- Chesapeake Beach Resort
- Lime Tree Bay Resort
- Hawks Cay Resort
- Baker's Cay Resort Key Largo, Curio Collection by Hilton
- Amara Cay Resort
- Bayside Inn Key Largo
- The Pelican Key Largo Cottages
- Fairfield Inn & Suites by Marriott Marathon Florida Keys
- Islander Resort
- Kingsail Resort
- Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
- Waterside Suites & Marina