Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Sugarloaf Key on Hotels.com. These Sugarloaf Key hotels consistently deliver on quality, location and traveler experience. Last updated on September 19, 2026.
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.
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.
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.
Set along the Florida Keys shoreline, this peaceful hotel offers easy access to Duval Street and Smathers Beach. Enjoy complimentary WiFi and parking while unwinding in the hot tub after exploring nearby Ernest Hemingway's Home.
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.
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.
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 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.
Coastal luxury meets convenience at this vibrant aparthotel near Florida Keys beaches. Just minutes from Ernest Hemingway's Home and Museum, enjoy a peaceful garden setting with hiking trails nearby. Perfect for exploring Key West's legendary attractions.
Key West's coastal hideaway features the island's largest pool, complete with hot tub and poolside bar. Cuban flavors await at Floridita Food Truck, while Duval Street and beaches are just minutes away. In-room refrigerators and microwaves enhance your tropical 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.
Between mangrove tunnels and crystal waters, this Florida Keys paradise offers adventures without the Key West crowds. Kayak through natural channels where great blue herons stand sentinel and manatees might glide beneath your paddle. The underwater wonderland of Looe Key National Marine Sanctuary beckons with its kaleidoscope of coral and tropical fish just offshore. Sugarloaf Beach provides a quiet alternative to busier shores, while local bars serve conch fritters and key lime cocktails with zero pretension. For a perfect day, paddle Upper Sugarloaf Sound in the morning, snorkel after lunch, then claim a spot at a waterfront bar where locals swap fishing tales as the sun melts into the Gulf.
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.
Loved the place. Beautiful and large pool. Free Shuttle service to downtown . Trolly stops right at door. Tiki bar on site is great. Room is awesome. Easy parking views are amazing. 2 free drinks at bar per each nights stay. Concierge sevice booked my dive trip.
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.
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!
We traveled as a family with 3 small children, so we liked having a hotel away from Duval street. It was convenient being a 5 min shuttle drive from the airport to the hotel. The grounds are beautiful and the pool was a good size. We liked that the pool was heated too. We ate breakfast at the hotel most days, and the food was pretty good with attentive service. The shuttle to the downtown area was about 10-15 mins away and dropped off/picked up at a good location around a lot of good...
Great for a relaxing weekend, quiet hotel not too far from the main tourist center. We love the shuttle service provided by the hotel and his driver Gerry who guided us in every short trips. The only advice to the hotel is to provide the housekeeping service everyday without being requested by the guest, we expected this service to be included since the hotel charged an extra 51.00 usd per night!
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. ...
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.
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.
We stayed two nights in the 3-bedroom suite. Everything, from the moment of arrival, was top rate. The front desk attendant was in contact with me via text to ensure a smooth and efficient check in before arrival and was a great help with local recommendations at check in. Departure took 30 seconds yet the desk attendant took the time to ask how everything was, if I needed anything, wished me well, etc. The suite was beautiful appointed and the furniture very functional and comfortable. Our...
The Duval House was absolutely precious. The garden courtyard was beautifully taken care of with plenty of nooks to sit in. The pool is mostly shaded for the hottest part of the day, which seemed especially valuable in comparison to other BnBs. Our room was very comfortable with probably the best bed I’ve been in at a hotel or BnB. And all of the staff was very responsive, friendly, and helpful. Even KissKiss, the property cat, made the rounds to our room to make sure everything was in perfect...
Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Sugarloaf Key on Hotels.com. These Sugarloaf Key hotels consistently deliver on quality, location and traveler experience. Last updated on September 19, 2026.