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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. Beautiful historic property in perfect location. Rooms were well appointed and very clean. Staff were friendly and helpful. A wonderful place to stay.
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.
Great location, only few minutes to Southernmost Point of the Continental U.S.A.
Mallory Square is about 20 min walk along Duval St, where most of restaurant are.
Staff at the Douglas House were exceptional, Jose is very friendly and helpful.
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. Wonderful resort right on the water, they have kayaks/paddle-boards/bikes available for use. We were able to snorkel right off the beach here and my son really enjoyed diving for seashells. The room was good with everything you might need in a kitchen. Very chilled out feeling, and beautiful sunsets. Cute little breakfast available.
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. Love the fact the apartment had a view and wash/dry machine, new furniture, lots of towels and all very clean and fresh The staff is very friendly too
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. We had a great time! Super kind and nice, clean and very comfortable. Great location.
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. Clean and easily to get around and the cabins were awesome
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. Everything, clean,calm,location,the nice staff,the lady in the office explained really good about it.
Islamorada
Situated in Islamorada, 3.1 km from Windley Key, Ragged Edge Resort & Marina features accommodation with free bikes, private parking, an outdoor swimming pool and a terrace. Located around 4 km from Theater Of The Sea On Islamorada, the resort with free WiFi is also 8.3 km away from Upper Matecumbe Key. Some units at the property have a balcony with a sea view. The property is perfect for staying on the Keys. It has everything you need to be comfortable and enjoy your stay. The room was super clean, the bed is very comfortable, the kitchen has all the gadgets, every building has a BBQ, and the common areas are beautiful. Great location, central and oceanfront. The staff was very kind. Definitely, I will return.
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
Couples travelling in Florida Keys loved staying at Happy in the Keys Tiny Home, Starfish Seas Key Largo Ocean Pointe 1302 and Your Happy Place ON THE BEACH!.
Similarly, these hotels with pools in Florida Keys are highly rated by couples: Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly, Villa Valbuena Ocean Pearl Key Largo Pool Restaurant Marina Pickleball and Villa Valbuena Aqua Vista Key Largo Marina Pickleball Remodeled 2025.
There are 917 hotels with pools in Florida Keys you can book on Booking.com.
The average price per night for a hotel with pools in Florida Keys for this weekend is US$767, based on current Booking.com prices.
Southernmost Point Guest House & Garden Bar, Simonton Court Historic Inn & Cottages and Douglas House are some 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.
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
Many families visiting Florida Keys loved staying at La Te Da - Adult Only, 21 or older, Gallego Deluxe Rental and Vacay Vibes-2 Pools, Pickleball, Coffee Bar, 2 Jacuzzis, Food Truck.
Similarly, Ocean View Treehouse Double King Suite 3403, Green Pineapple and Nauti Hideaway Ocean Pointe 2314 are also popular among family travellers.
Coconut Cay Marina & RV Park, The Gardens Hotel and Sugarloaf Key Hotel at KOA Resort have received great reviews from guests in Florida Keys regarding the views from these hotels with pools
Guests staying in Florida Keys also spoke highly of the views from these hotels with pools: Coconut Bay Resort - Key Largo, Pines & Palms Resort and Hyatt Vacation Club at Windward Pointe.
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