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.
Escape to this beachside haven with 5 outdoor pools, umbrella-dotted shores, and full spa offering facials and massages. Just minutes from Sombrero Beach, enjoy two bars, a poolside lounge, and Mahina restaurant after a workout in the fitness center.
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.
Experience Florida Keys laid-back charm at this waterfront hotel with a marina and outdoor pool. Grab seafood at Porky's Bayside restaurant, explore Marathon on complimentary bikes, or drive just minutes to Sombrero Beach's soft sands.
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.
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.
Breezy oceanfront getaway offering a refreshing pool and 24-hour fitness center. Just minutes from Duval Street and water activities like scuba diving. Enjoy restaurant dining and bar service with easy access to Key West's famous beaches.
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.
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 in Key West serenity with sunset vistas from this oceanfront haven. Just minutes from Smathers Beach and Duval Street, enjoy the private beach, outdoor pool, and hot tub after exploring nearby attractions via the complimentary shuttle.
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.
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.
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 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
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...
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!
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.
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..
The Grand Guesthouse is a gem in Key West! The host was outstanding and the facility was lovely. Breakfast was simple but nice, and the Happy Hour was an added bonus. We had a nice suite- a bedroom and a living/kitchen area.
The room was nicely appointed and it was straightened by the staff each day. The room was very clean! Overall, my wife and I were impressed!
Two small improvements... the mattress was too firm. Also, the wifi was not strong enough in our room to stream anything. ...
Love Love Loved this hotel. I rented the two level two BR model for just me and my wife b/c I snore. Rooms are well soundproofed :) Very comfy beds. Perfect for two couples or fam w kids. Pricier than other hotels but value was off the charts! Kitchen had everything...thoughtful yummy complimentary snacks were left for us every night when we rolled in. Front deck young ladies so helpful with tips for restaurants. They pulled no punches and if a place was a ripoff, they let us know. Walk up Cuban...
