Escape to this serene Florida Keys retreat featuring multiple outdoor pools and a relaxing hot tub. Located just minutes from stunning beaches, enjoy convenient amenities like free WiFi and parking while exploring nearby Upper Sugarloaf Key attractions.
Feel the coastal breeze at this Big Pine Key marina resort where adventure awaits. Hike scenic trails, kayak crystal waters, or lounge by the pool. Near Blue Hole and Bahia Honda State Park, with rooms featuring microwaves and free WiFi.
Dive into a tropical oasis at this Key West resort featuring a marina, poolside bar, and complimentary bicycles. Just minutes from Smathers Beach and Duval Street, guests love the 24-hour fitness center and helpful staff.
This garden hotel offers a relaxing escape with outdoor pool, jacuzzi, and poolside bar. Just minutes from Key West Airport with a free area shuttle to nearby attractions including Duval Street and Smathers Beach.
Experience oceanfront bliss at this peaceful retreat with stunning sunset views. Just a 5-minute drive from Smathers Beach and Florida Keys Beaches, enjoy the outdoor pool, poolside bar, and complimentary breakfast before exploring nearby Duval Street with the convenient shuttle service.
Soak up the sunshine at this Marathon beach hotel with cabanas and loungers. Just 10 minutes from Sombrero Beach, this resort offers 2 outdoor pools, a poolside bar, and The Bistro serving American cuisine. The full-service spa provides rejuvenating treatments.
This beachfront resort offers a full-service spa for ultimate relaxation after sun-filled days. Enjoy cuisine at El Farito, one of 4 restaurants, or drinks at multiple bars while marina views unfold. Just a short drive from Sombrero Beach and local art galleries.
Escape to this waterfront retreat with a marina, where 2 outdoor pools and poolside bars await. Feast on seafood at Matt's Stock Island, then explore nearby Duval Street and Smathers Beach. A 24-hour fitness center and free WiFi complete your Key West getaway.
Enjoy incredible views of the Atlantic from this Key West hotel with spacious accommodations featuring washers/dryers and refrigerators. The outdoor pool, hot tub, and snack bar create a relaxing atmosphere near Duval Street with free WiFi and parking.
Immerse in tropical living at this family-friendly resort near Duval Street and Smathers Beach. Enjoy 2 restaurants including the Toasted Coconut serving American cuisine, plus 2 poolside bars, a hot tub, and 24-hour fitness center, all with free WiFi.
Immerse yourself in Key West charm at this beachside retreat with an indoor pool. Located near iconic spots like Southernmost Point and Smathers Beach, the hotel offers easy access to kayaking, scuba diving, and snorkeling adventures with 24-hour service.
Escape to this Marathon aparthotel featuring an outdoor pool and apartments with premium bedding. Located within a 15-minute drive of Sombrero Beach and Vaca Key, guests enjoy free WiFi and parking. The helpful staff and clean rooms earn top marks.
Escape to this beachfront haven with 4 sparkling pools and onsite kayaking. The Grove Kitchen serves meals by the water, while a fitness center keeps you active. Just minutes from Duval Street and Smathers Beach, with easy airport access.
Enjoy serenity at this peaceful waterfront retreat with a private beach, outdoor pool, and water adventures like kayaking and sailing. Four Marlins restaurant serves local cuisine, while the spa offers rejuvenating massages just minutes from Duval Street.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Escape the tourist rush at Cutthroat Harbor Estates, a peaceful slice of paradise on Summerland Key. This residential waterfront neighborhood offers crystal-clear waters perfect for fishing, kayaking, and boating from your private dock. The low-rise coastal homes on stilts create a genuine Keys atmosphere where you can spot tropical birds and enjoy breathtaking sunset views.
You'll need to drive to nearby Cudjoe Key or Summerland Key for dining options featuring fresh seafood and Caribbean flavors. Vacation rental homes with waterfront views dominate accommodation choices. The neighborhood's layout prioritizes privacy and seclusion, making it ideal for travelers seeking the authentic Florida Keys lifestyle.
Sugarloaf Shores delivers waterfront paradise without the tourist crowds. Private canals weave between stilted homes where you can launch kayaks right from your rental's backyard dock. The crystal-clear backcountry waters beckon with world-class fishing, while gentle waves provide perfect spots for swimming and snorkeling.
Dining and shopping require a short drive, as this peaceful residential enclave focuses on natural beauty rather than commercial offerings. Most visitors stay in spacious vacation homes with private pools and boat docks. A rental car is essential for exploring the rest of the Florida Keys from this secluded waterfront haven.
Cudjoe Gardens offers a slice of authentic Florida Keys living with canal-front homes where you can park your boat right out back. This peaceful residential retreat lets you escape the crowds while still having easy access to the surrounding waters. Wildlife enthusiasts will spot herons stalking the shallows and fish jumping at sunrise while the gentle sound of water lapping against docks creates your vacation soundtrack.
Nearby restaurants in Summerland Key and Cudjoe Key serve up fresh seafood just a short drive away. Most homes feature private pools, boat docks, and tropical landscaping, all designed for relaxation and water activities. A rental car is essential for exploring the area, as this quiet community focuses on waterfront living rather than tourist amenities.
Breezeswept Beach Estates is a slice of Florida Keys paradise where private docks and waterfront homes replace tourist traps. You'll spend your days exploring crystal-clear waters, spotting marine life while kayaking, or casting a line into the Gulf. The surrounding Newfound Harbor Keys and nearby islands offer perfect day-trip adventures when you're ready to venture beyond your peaceful retreat.
Vacation rentals with tropical landscaping and breezy porches make up the accommodation options here. You'll need a car to reach restaurants on Ramrod Key or stock up on groceries for cooking. The quiet streets and gentle waves create the perfect soundtrack for stargazing and disconnecting from the everyday hustle.
Whether you want to collect beach glass or watch the sunset, Sugarloaf Beach is a spot you might want to check out, located 8.1 mi (13 km) from central Summerland Key. Catch the sunset by the shore at Florida Keys Beaches, just a short walk away.
Listen to the relaxing sound of the water and take some great vacation pics at Upper Sugarloaf Sound located 6.3 mi (10.2 km) from central Summerland Key.
Rooms were right on the water with great views, property had some nice amenities and the boat ramp and slips were exactly what I needed. Annette at the front desk was super friendly and knows the true meaning of Customer Service. Because of her, we will be back for sure and tell all our friends, this is the place to stay!
Upon our arrival, the sight of 2 iguanas on the lounging on the bridge by the pristine water at the back of the property had my entire family out of the minivan at lightning speed. They followed one, which lead them to trees full of these beautiful lizards. The front desk personnel, a very amiable gentleman, was very friendly and welcoming. Our room was in the middle of the 2nd floor, and had a fantastic view of the bay. And yes, there were more iguanas looking at us from the first floor, some...
The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food.
The service was over the top! From the front desk to the cleaning staff, everyone was friendly and always looking to do more. Room and hotel had a boutique feel that you don't see with the chain hotels. Also the location is ideal. One block off the action. Duval street is loud and crazy, but turn into the hotel and it suddenly becomes quite and comfortable. We will definitely be back
This was great place to stay and was in a great location. Every thing was in walking distance and was only about 100 yards off Duval Street yet on the hotel property the gardens made you feel like you were in the middle of nowhere. I would highly recommend this place and we stay there next time I am back in Key West.
The Douglas House served as a perfect home base while in Key West. The location allows for easy access to all Duval has to offer. Really enjoyed being able to hear the national anthem being played every morning at 8 from the Navy base..
My husband and I recently stayed at H2O Suites for 3 nights. The property was immaculate, the staff was extremely friendly and helpful, and our room was large and comfortable. We had a suite that had a plunge pool - this was amazing!! We used it several times daily. The location is perfect - one block from Duval, so everything is easily accessed, but it’s very quiet. We rented bikes from the hotel (easy parking right out back) and truly enjoyed our getaway. Cannot day enough good things about...
Absolutely wonderful destination fir a relaxing stay while in Key West. Can not say enough about the great staff— friendly, helpful, just happy to be working here. They could not be more accommodating!! Add to that complimentary wine in your room, daily happy hours by the pool, and full service cooked breakfasts that easily saves you hundreds of dollars on a 4- day stay. Can not give this place enough praise. We are already planning a return trip.
Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...
Beautiful property and amazing owners and staff. Very kind and generous. The property is perfectly located to Duval St. and lots of bars and restaurants. The pool is heated to a perfect temperature. The rooms are beautifully appointed and large. Just be aware that this is not an adult only property, so children can be a factor.
This was perfect for our family. We brought nanny, and got the two bedroom. Our young girls slept on the pull out couch. Pool is beautiful, cute bar. No beach… the pictures on the website trick you into thinking beach is right there. They also don’t clean your room everyday.
We had a fine stay. Our room was secluded. That is a good description. All the little balconies had a real secluded feel. Views to the other balconies were all obscured. Staff was game on. The cafe is recognized as one of the best restaurants on the island, get a dinner reservation well in advance of your stay.
The room was clean and neat, everyone is very friendly and helpful. So glad we booked this place last minute. The best time we've ever had in Key west. You will not get anything more authentic than this place. Loved it!
We stayed here for one night for my husband's 40th birthday. The hotel was aware we were celebrating an occasion and offered complimentary refreshment's in our room. We were able to check on early, got upgraded to pool view and also checked out late!
When we arrived we were amazed with how huge the suite was. It was the same size as a condo. The decor was beautiful and the entire place was immaculate, including the outside. What we liked most was how quiet and relaxing the place was (there...
If you're looking for the flexibility to change your travel plans to Summerland Key, most properties offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Summerland Key if I want a vacation rental instead of a traditional hotel?
If you're looking for a good alternative to a hotel, look over our selection of 488 vacation homes. You can also consider one of 8 villas or 48 cottages for your stay.
What will the weather in Summerland Key be like during my trip?
Summerland Key is a great place to visit any time of year with an average temperature of 73°F during the coldest months.
Why should I book my Summerland Key hotel with Hotels.com?
There are lots of reasons to book your Summerland Key trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.
