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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. This hotel was great . Everything about it . Starting with the blonde lady in front desk and the Argentinian waiter in the beach . Top service . Food and rooms amazing best hotel In Key west far down
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.
Everything as promised, partly even better. We had a very pleasant stay. Great Place.
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.
Great accommodation and the staff was super friendly. Nice breakfast and good facilities!
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. Great place, quiet with good facilities and great staff.
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. Great apartment in beautiful and quiet surroundings, all a short drive from Key West.
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 stayed 8 nights recently and had the absolute best experience we booked two more stays! The staff, especially John & I believe her name was Sabrina were top notch and so helpful! We cooked in most nights as everything we needed was there!! We had enough towels for our entire stay, and they even had pool towels for us to use! Will definitely help with packing next time! We used the kayaks, the grill, and the pool was nice and clean. During our stay they were constantly doing upkeep, and I heard they were even getting aqua lodges soon! 10/10 for sure!
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. The view was everything! The place was spotless and had all items we needed to make it comfortable for our 4 night stay. The beds were comfortable. This was a fantastic place to stay and we will be back!!
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 Your Happy Place ON THE BEACH!, Starfish Seas Key Largo Ocean Pointe 1302 and Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly.
Similarly, these hotels with pools in Florida Keys are highly rated by couples: Villa Valbuena Aqua Vista Key Largo Marina Pickleball Remodeled 2025, Key Largo Baha Penthouse Ocean Pointe 1416 and Villa Valbuena Ocean Pearl Key Largo Pool Restaurant Marina Pickleball.
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: Pines & Palms Resort, Coconut Bay Resort - Key Largo and Hyatt Vacation Club at Windward Pointe.
Most hotels with pools on Booking.com offer free cancellation.
Southernmost Point Guest House & Garden Bar, Douglas House and Simonton Court Historic Inn & Cottages 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.
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 Key Largo Baha Penthouse Ocean Pointe 1416, Vacay Vibes-2 Pools, Pickleball, Coffee Bar, 2 Jacuzzis, Food Truck and Happy in the Keys Tiny Home.
Similarly, Green Pineapple, Your Happy Place ON THE BEACH! and Modern and Coastal Ocean Pointe 2307 are also popular among family travellers.
The average price per night for a hotel with pools in Florida Keys for this weekend is US$820, based on current Booking.com prices.
There are 916 hotels with pools in Florida Keys you can book on Booking.com.
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