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 welcomes guests with a restaurant and a terrace. Guests can make use of a bar. The family room is beautiful and comfortable.
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. Great location, spacious room, free parking and daily drinks included.
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.
Very friendly , beautiful location, delicious breakfast
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. The facilities was very clean. Great value for money. Will definitely recommend.
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. 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 facility, location the staff attitude. The view from the room.
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
Southernmost Point Guest House & Garden Bar, Simonton Court Historic Inn & Cottages and Atlantic Bay Resort are some popular hotels with pools in Florida Keys.
In addition to these hotels with pools, The Capitana Key West, Douglas House and Key West Villas are also popular 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 Duval Street Suite w parking and heated pool.
Similarly, these hotels with pools in Florida Keys are highly rated by couples: Key Largo Sunrise Resort Style Ocean Pointe 5315, Key Largo Baha Penthouse Ocean Pointe 1416 and Villa Valbuena Aqua Vista Key Largo Marina Pickleball Remodeled 2025.
Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly, The Gardens Hotel and Pines & Palms 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, Sugarloaf Key Hotel at KOA Resort and Coconut Palm Inn.
The average price per night for a hotel with pools in Florida Keys for this weekend is US$862, based on current Booking.com prices.
Many families visiting Florida Keys loved staying at Key Largo Baha Penthouse Ocean Pointe 1416, Gallego Deluxe Rental and Your Happy Place ON THE BEACH!.
Similarly, Nauti Hideaway Ocean Pointe 2314, La Te Da - Adult Only, 21 or older and Green Pineapple are also popular among family travellers.
There are 980 hotels with pools in Florida Keys you can book on Booking.com.
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