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Key West
Situated in Key West, 2.1 km from Smathers Beach, The Capitana Key West features accommodation with an outdoor swimming pool, free private parking, a fitness centre and a private beach area. Boasting a 24-hour front desk, this property also welcomes guests with a restaurant and a terrace. Guests can make use of a bar. Super excellent service from check-in to check-out. Front Staff, pool team, cleaning.. all was great. We stayed in one of cottages, something we can recommend.
Duval, Key West
This Key West, Florida Southernmost Point Guest House & Garden Bar is located on Duval Street 110 metres from the Southernmost Point and 73 metres from the beach. Features include a free hot American breakfast and a hot tub.The property is located across 4 buildings. Amazing place - well kept, charming and great location!
Duval, Key West
Located just 2 minutes’ walk from the Ernest Hemingway Home and Museum, this adult-only inn features free parking and a shared outdoor swimming pool. Free Wi-Fi is also available.
A tropical garden and access to sun terraces can help guests enjoy the Florida scenery. Luggage storage, vending machines and non-smoking rooms are also available.
Cute, small still spacious house. Very good location, parking place included.
Duval, Key West
Located in Key West, this Florida adult-only inn offers complimentary, light continental breakfast and free Wi-Fi access. Duval Street is 2 minutes’ drive from the property and The Ernest Hemingway Home and Museum is 3 minutes’ drive away.
Guests can enjoy swimming any one of the 4 on-site outdoor pools, use the bicycle hire, or relax in the garden.
Pool is fantastic. Hotel got perfect atmosphere and is setup in beautiful garden.
Tavernier, Key Largo
Located in Tavernier, this beachfront Florida resort is 2 miles from Florida Keys Wild Bird Center. Guests will enjoy snorkeling near the hotel's private beach, an outdoor pool, and free property-wide Wi-Fi. Very nice close to the bay great landscaping
Summerland Key
Situated in Summerland Key, 32 km from Ernest Hemingway Home and Museum, Sugarloaf Key Hotel at KOA Resort features accommodation with an outdoor swimming pool, free private parking, a private beach area and a restaurant. This 3-star hotel offers a bar. Featuring free WiFi throughout the property, the non-smoking hotel has a hot tub and evening entertainment. Everything was amazing, high end new apartment with absolutely everything needed. Spacious bedroom and kitchennete with living room. Good thinking with providing dishwasher tablets and detergent so guest can maintain cleaners during stay. Great facility with swimming pool and jacuzzi sorounded by green so there is privacy. Kids had plenty activities Extra thank you for preventing place with mosquito spraying.
Islamorada
Situated in Islamorada, less than 1 km from Upper Matecumbe Key, Casa Morada features accommodation with free bikes, free private parking, an outdoor swimming pool and a garden. Featuring a terrace, the 5-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. The hotel has a hot tub and luggage storage space. The location is perfect. The property is lush and beautiful. Daily housekeeping is a plus. Hot breakfast was added this year (eggs & potatoes). Great food from the Thai Food truck located on the property. Sunset Sail was awesome (also located on the property). Free use of kayaks, paddleboards and bicycles.
Marathon
Situated in Marathon, 2.4 km from Sunset Park Beach, Cabins at Bonefish Bay features accommodation with free bikes, free private parking and an outdoor swimming pool. The property is set 46 km from Upper Matecumbe Key, 50 km from Theater Of The Sea On Islamorada and 600 metres from A Deep Blue Dive Center. Free WiFi is available throughout the property and Florida Keys Aquarium Encounters is 1.2 km away. super comfortable and well maintained, very clean
Summerland Key
Offering an outdoor swimming pool and lake view, Sugarloaf Key RV Resort & Cottages is situated in Summerland Key, 32 km from Ernest Hemingway Home and Museum and 32 km from Duval Street. The property is located 32 km from Southernmost Point, 32 km from Key West Aquarium and 32 km from Mallory Dock. Outdoor seating allows guests to sit outside and enjoy the good weather. Very clean, almost new cottage.
Marathon
Set in Marathon, 3.7 km from Florida Keys Aquarium Encounters, Coconut Cay Marina & RV Park offers accommodation with free bikes, free private parking, an outdoor swimming pool and a private beach area. The property is located 3.9 km from Captain Hook S Marina Dive Center, 5.1 km from A Deep Blue Dive Center and 6.7 km from Seven Mile Bridge. The hotel provides lake views, a terrace, and free WiFi is available throughout the property. It is such a unique and cool experience, made better with the free kayaks that you can use to go find manatees! It’s close (short drive/bike ride) to good restaurants, and has an amazing sundowner spot. Definitely recommended!
Hotel with Pools in Key West
Popular with guests booking hotels with pools in Florida Keys
Hotel with Pools in Key West
Popular with guests booking hotels with pools in Florida Keys
Hotel with Pools in Key West
Popular with guests booking hotels with pools in Florida Keys
Hotel with Pools in Key West
Popular with guests booking hotels with pools in Florida Keys
Hotel with Pools in Key West
Popular with guests booking hotels with pools in Florida Keys
Hotel with Pools in Key West
Popular with guests booking hotels with pools in Florida Keys
Many families visiting Florida Keys loved staying at Modern and Coastal Ocean Pointe 2307, La Te Da - Adult Only, 21 or older, and Your Happy Place ON THE BEACH!.
Similarly, Latitude Penthouse Key West, Vacay Vibes-2 Pools, Pickleball, Coffee Bar, 2 Jacuzzis, Food Truck, and Happy in the Keys Tiny Home are also popular among families.
There are 916 hotels with pools in Florida Keys you can book on Booking.com.
Couples traveling in Florida Keys loved staying at Happy in the Keys Tiny Home, Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly, and Starfish Seas Key Largo Ocean Pointe 1302.
Similarly, these hotels with pools in Florida Keys were also highly rated by couples: Villa Valbuena Aqua Vista Key Largo Marina Pickleball Remodeled 2025, Your Happy Place ON THE BEACH!, and Villa Valbuena Ocean Pearl Key Largo Pool Restaurant Marina Pickleball.
Southernmost Point Guest House & Garden Bar, Douglas House, and Simonton Court Historic Inn & Cottages are some of the popular hotels with pools in Florida Keys.
In addition to these hotels with pools, The Capitana Key West, Atlantic Bay Resort, and Key West Villas are also popular in Florida Keys.
The average price per night for a hotel with pools in Florida Keys for this weekend is $805, based on current Booking.com prices.
The Gardens Hotel, Sugarloaf Key Hotel at KOA Resort, and Pines & Palms Resort have received great reviews from guests in Florida Keys about the views from these hotels with pools
Guests staying in Florida Keys also loved the views from these hotels with pools: Coconut Bay Resort - Key Largo, Coconut Palm Inn, and Hyatt Vacation Club at Windward Pointe.
Most hotels with pools on Booking.com offer free cancellation.
We make it quick and easy to book a hotel with pools in Florida Keys. Here’s what we offer:
• Free cancellation on most stays
• We Price Match
• 24/7 customer support in 40+ languages
Extraordinary place with four swimming pools and wonderful atmosphere
Very nice appartement with a great view. There is a swimming pool and nice restaurants on the other side of the water with live music. Great to sit on your own balcony and enjoy the live music from the restaurant. Highly recommend snorkling tour which departs from the appartments.
loved the quirkiness of this place, right in the centre of the night life district although a quiet room great for night life and restaurants. Staff super friendly and breakfast was very good. Court yard swimming pool a bonus all the rooms are different and non corporate typical Key West Flair.
Swimming pool
The buildings are beautiful both indoors and outdoors. We loved the garden with its beautiful vegetation that provided delightful shade. We also had a lot of fun in the the pool, and it was so nice to have our own veranda/outdoor deck.
Location is good. Well situated within the keys. Good resort facilities for free hire. Swimming pool and tiki bar are nice. Reception and lounge area is nice.
Everything was great, we really appreciated using the kayaks, the swimming pool and the spa. The greenery in the surroundings makes the place very delightful.
The breakfast was very nice, service was friendly, location easily accessible by car, the hot tube was pleasant, swimming pool was also good
Outdoor patio is nice and the room has a great shower. The swimming pool is a great option after a long day. You can use a kayak and fishing rods. One hour drive to Key West. Breakfast is basic but fine and served in a ziplock bag. Restaurant in walking distance.
nice swimming pool! very friendly staff great picknick tables and other outdoor furniture