Florida Keys Hotels with Swimming Pool
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4 Sept - 6 SeptNext weekend
11 Sept - 13 SeptOur top choices for Florida Keys hotels with a pool
1. 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.
RM268
RM574 total
includes taxes & fees
2 Sept - 3 Sept
RM320
RM403 total
includes taxes & fees
27 Sept - 28 Sept
3. Beachside Resort & Residences
Beachside Resort & ResidencesKey West
- Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
RM387
RM820 total
includes taxes & fees
20 Sept - 21 Sept
4. Hampton Inn Key West FL
Hampton Inn Key West FLKey West
- Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.
RM561
RM632 total
includes taxes & fees
20 Sept - 21 Sept
5. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
- Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
RM480
RM767 total
includes taxes & fees
15 Sept - 16 Sept
6. 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.
RM459
RM757 total
includes taxes & fees
7 Sept - 8 Sept
7. 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.
RM765
RM1,042 total
includes taxes & fees
22 Sept - 23 Sept
8. Kingsail Resort
Kingsail ResortMarathon
- Sleek outdoor pool with marina views makes waterfront adventures a dream at Kingsail resort.
RM283
RM318 total
includes taxes & fees
17 Sept - 18 Sept
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Hotels with pools and free breakfast in Florida Keys
RM268
RM574 total
includes taxes & fees
2 Sept - 3 Sept
RM411
RM553 total
includes taxes & fees
29 Sept - 30 Sept
RM561
RM632 total
includes taxes & fees
20 Sept - 21 Sept
RM480
RM767 total
includes taxes & fees
15 Sept - 16 Sept
RM459
RM757 total
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys CollectionNew Town
RM442
RM610 total
includes taxes & fees
22 Sept - 23 Sept
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Alexanders Guesthouse - Adult Exclusive, LGBTQ FriendlyOld Town Key West
RM395
RM597 total
includes taxes & fees
8 Sept - 9 Sept
RM299
RM336 total
includes taxes & fees
14 Sept - 15 Sept
RM443
RM752 total
includes taxes & fees
22 Sept - 23 Sept
RM585
RM952 total
includes taxes & fees
9 Sept - 10 Sept
4-star hotels with pools in Florida Keys
RM320
RM403 total
includes taxes & fees
27 Sept - 28 Sept
RM585
RM952 total
includes taxes & fees
9 Sept - 10 Sept
RM459
RM757 total
includes taxes & fees
7 Sept - 8 Sept
RM561
RM1,140 total
includes taxes & fees
17 Sept - 18 Sept
RM656
RM969 total
includes taxes & fees
14 Sept - 15 Sept
RM443
RM752 total
includes taxes & fees
22 Sept - 23 Sept
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key WestKey West
RM459
RM652 total
includes taxes & fees
7 Sept - 8 Sept
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by HiltonOld Town Key West
RM743
RM1,107 total
includes taxes & fees
29 Sept - 30 Sept
Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West Resort and SpaKey West Historic District
RM813
RM1,196 total
includes taxes & fees
29 Sept - 30 Sept
RM581
RM847 total
includes taxes & fees
30 Sept - 1 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
Bayside Inn Key Largo
10/10 Excellent
"this is the 2nd time I have stayed here, and the staff is incredibly helpful and friendly."
Playa Largo Resort & Spa, Autograph Collection
10/10 Excellent
"Perfection!"
Amara Cay Resort
10/10 Excellent
"Wonderful resort, very friendly staff, would definitely stay again!"
Cheeca Lodge & Spa
8/10 Good
"Amenities and the property are absolutely beautiful. Mixed feelings about the staff. The bartenders and pool waitress get an A+. Everyone else could be friendlier :) No problems getting through the gate, which I've had issues with at other properties. Even when the night guard steps away, they will send security in less than a minute to open the gate for you so that was great. We enjoyed our stay and I would go back."
Baker's Cay Resort Key Largo, Curio Collection by Hilton
10/10 Excellent
"Nous n avons pas pris l option petit dej . Le parking devait être inclus mais il nous a été facturé ."
Waterside Suites & Marina
10/10 Excellent
"Rainbow Reef is next door. Huge patio to dry gear. Scuba divers perfect spot!"
Islander Resort
8/10 Good
"Great property with an amazing concept, especially in an area where there aren’t many high-end properties offering this style and experience. The facilities are excellent, and overall we really enjoyed our stay. My only negative feedback is that a few members of staff were constantly on their phones watching clips and videos, often with the volume turned up. We found this quite annoying, particularly when trying to relax quietly by the pool. It would be great if staff could be reminded to use headphones or keep phone use to a minimum in guest relaxation areas. Room maintaince could also be better."
Hampton Inn Key Largo Manatee Bay
10/10 Excellent
"The staff was amazing and very, very helpful! Amazing at trouble shooting and went over the top to help us out! The breakfast was very good, better than you would expect for a hotel and we really enjoyed the waterfront area."
Chesapeake Beach Resort
10/10 Excellent
"Lindo y acogedor lugar, cerca del sandbar con marina para poner tu bote. Nuestra eetancia fue excelente. El staff bien amable y atento. Volveremos Gracias"