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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Sep 1 - Sep 2Tomorrow
Sep 2 - Sep 3This weekend
Sep 4 - Sep 6Next weekend
Sep 11 - Sep 13Our 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.
₩91,082
₩194,787 total
includes taxes & fees
Sep 2 - Sep 3
₩102,668
₩129,361 total
includes taxes & fees
Sep 28 - Sep 29
3. Beachside Resort & Residences
Beachside Resort & ResidencesKey West
- Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
₩131,358
₩278,554 total
includes taxes & fees
Sep 15 - Sep 16
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.
₩190,733
₩214,575 total
includes taxes & fees
Sep 20 - Sep 21
5. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
- Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
₩163,086
₩260,399 total
includes taxes & fees
Sep 2 - Sep 3
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.
₩155,879
₩257,119 total
includes taxes & fees
Sep 8 - Sep 9
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.
₩259,953
₩353,989 total
includes taxes & fees
Sep 15 - Sep 16
8. Kingsail Resort
Kingsail ResortMarathon
- Sleek outdoor pool with marina views makes waterfront adventures a dream at Kingsail resort.
₩95,009
₩106,884 total
includes taxes & fees
Sep 15 - Sep 16
View all properties
Hotels with pools and free breakfast in Florida Keys
₩91,082
₩194,787 total
includes taxes & fees
Sep 2 - Sep 3
₩139,725
₩187,962 total
includes taxes & fees
Sep 29 - Sep 30
₩190,733
₩214,575 total
includes taxes & fees
Sep 20 - Sep 21
₩163,086
₩260,399 total
includes taxes & fees
Sep 2 - Sep 3
₩155,879
₩257,119 total
includes taxes & fees
Sep 8 - Sep 9
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys CollectionNew Town
₩149,971
₩207,188 total
includes taxes & fees
Sep 22 - Sep 23
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Alexanders Guesthouse - Adult Exclusive, LGBTQ FriendlyOld Town Key West
₩134,162
₩202,583 total
includes taxes & fees
Sep 8 - Sep 9
₩101,544
₩114,235 total
includes taxes & fees
Sep 3 - Sep 4
₩150,436
₩255,549 total
includes taxes & fees
Sep 16 - Sep 17
₩198,671
₩323,518 total
includes taxes & fees
Sep 8 - Sep 9
4-star hotels with pools in Florida Keys
₩102,668
₩129,361 total
includes taxes & fees
Sep 28 - Sep 29
₩198,671
₩323,518 total
includes taxes & fees
Sep 8 - Sep 9
₩155,879
₩257,119 total
includes taxes & fees
Sep 8 - Sep 9
₩190,507
₩387,407 total
includes taxes & fees
Sep 20 - Sep 21
₩222,919
₩329,256 total
includes taxes & fees
Sep 15 - Sep 16
₩150,436
₩255,549 total
includes taxes & fees
Sep 16 - Sep 17
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key WestKey West
₩155,879
₩221,521 total
includes taxes & fees
Sep 8 - Sep 9
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by HiltonOld Town Key West
₩252,254
₩376,099 total
includes taxes & fees
Sep 29 - Sep 30
Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West Resort and SpaKey West Historic District
₩276,255
₩406,177 total
includes taxes & fees
Sep 29 - Sep 30
₩197,326
₩287,636 total
includes taxes & fees
Sep 30 - Oct 1
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
Amara Cay Resort
10/10 Excellent
"It was a wonderful experience all around!!"
Cheeca Lodge & Spa
10/10 Excellent
"This was our second stay at Cheeca Lodge, and while the property remains as beautiful as ever, the outstanding staff made this visit truly exceptional! At check-in, Lola at the front desk gave us an incredible welcome. She was not only warm and friendly, but incredibly helpful—making us feel genuinely valued despite having stayed here before. Later that evening, we dined at Atlantic Edge, where Soso took wonderful care of us. Her customer service was top-notch, and she went above and beyond by providing great recommendations for my vegetarian diet. We had a fantastic experience and are already planning to bring our entire family back for our next trip!"
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!"
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."
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
10/10 Excellent
"we loved it !!!"