See the latest prices and deals by choosing your dates.
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 has a restaurant and a terrace. Guests can make use of a bar. Very clean, room was large and comfortable and view was amazing
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. Location, parking spot, cleanliness, excellent breakfast.
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.
Key west has a very good vibe with friendly folks and a feeling of inclusivity..
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 hotel and value for money. The location was perfect and the staff was very nice and helpful (especially Agostina, that showed us around and helped us with anything we needed).
Thank you!
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. The grounds were stunning and so well maintained - there were so many things provided for entertainment like pool, bikes, corn hole, table tennis, bikes and more. The staff were welcoming and it was a super relaxing place.
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 place, very clean and very well equipped.
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
Situated in Summerland Key, 32 km from Ernest Hemingway Home and Museum, Sugarloaf Key RV Resort & Cottages features air-conditioned rooms with free WiFi. With lake views, this accommodation provides a swimming pool. Key West Aquarium is 32 km from the holiday home and Mallory Dock is 32 km away. The cabin was one block from the best amenities I’ve ever stayed in!! It was absolutely beautiful with a great view, super comfy bed, amazing shower, big TV and wonderful little patio with water view!
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. Very well equipped too be a small place
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, Villa Valbuena Ocean Pearl Key Largo Pool Restaurant Marina Pickleball and Starfish Seas Key Largo Ocean Pointe 1302.
Similarly, these hotels with pools in Florida Keys are highly rated by couples: Villa Valbuena Aqua Vista Key Largo Marina Pickleball Remodeled 2025, Islamorada Paradise Overlooking the Fabulous Florida Bay. and Your Happy Place ON THE BEACH!.
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
There are 954 hotels with pools in Florida Keys you can book on Booking.com.
Many families visiting Florida Keys loved staying at Villa Valbuena Aqua Vista Key Largo Marina Pickleball Remodeled 2025, Green Pineapple and Modern and Coastal Ocean Pointe 2307.
Similarly, Your Happy Place ON THE BEACH!, Happy in the Keys Tiny Home and La Te Da - Adult Only, 21 or older are also popular among family travellers.
Most hotels with pools on Booking.com offer free cancellation.
The average price per night for a hotel with pools in Florida Keys for this weekend is US$601, based on current Booking.com prices.
Southernmost Point Guest House & Garden Bar, Simonton Court Historic Inn & Cottages and The Capitana Key West are some popular hotels with pools in Florida Keys.
In addition to these hotels with pools, Douglas House, Atlantic Bay Resort and Key West Villas are also popular in Florida Keys.
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, Hyatt Vacation Club at Windward Pointe and Coconut Palm Inn.
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