725 Truman Avenue, Downtown Key West, Key West, FL 33040, United States
#34 of 51 B&Bs and Inns in Key West
Guests' ChoiceBased on 872 hotel reviews
8.6Cleanliness
8.9
Comfort
9.0
Location
9.4
Facilities
8.8
Staff
9.1
Value for money
7.8
Free WiFi
8.5
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End of dialog contentReviewed: 1 September 2025
Mariluz
United StatesTo be honest the food I don’t eat cold food
I love the location walkable and very relaxing
Stayed in August 2025
Reviewed: 29 August 2025
Nicole
United StatesVery relaxing 😎
Very peaceful ☺️
Stayed in August 2025
Reviewed: 22 August 2025
Pamela
United StatesLocation
Stayed in August 2025
Reviewed: 22 August 2025
Margaret
United KingdomNothing
Everything was perfect
Stayed in August 2025
Reviewed: 18 August 2025
John
United StatesLocation, common areas, room
Stayed in August 2025
Reviewed: 13 August 2025
Brian
United KingdomStaff were unreal, could not have been more helpful, Buffett breakfast was amazing, great selection
Stayed in August 2025
Reviewed: 5 August 2025
Ashley
United KingdomWater pressure in the shower but that is nit picking. 😂
The venue itself was incredibly lush and the split of the pools. Location was excellent but far enough away to be quiet. Bar amenities were available but we didn't use these too much.
Stayed in August 2025
Reviewed: 31 July 2025
Jamie
United StatesBeautiful place
Stayed in July 2025
Reviewed: 26 July 2025
Steven
United StatesRoom had no tables to use a laptop or computer. Bugs were present but may be unavoidable due to the extremely hot and humid climate.
Breakfast was good but it was mainly carbohydrates. I was hoping for more choices of warm eggs. Coffee was excellent.
Stayed in July 2025
Reviewed: 23 July 2025
Linda
United StatesPet friendly
Stayed in May 2025
Reviewed: 23 July 2025
Jacob
United StatesN/A!
The staff was very friendly and helpful with everything we needed. We were welcomed with a pirate token, good for any drink at the bar for each of us. The breakfast exceeded my expectations; it's not your typical hotel breakfast. It was fresh and actually satisfying, not the usual sugary mess. The 3 pools were well kept and a comfortable temperature with towels as needed. The room was clean and comfortable. The bed was extremely comfortable. Location was perfect, quick walk over to Duval street. Highly recommened!
Stayed in July 2025
Reviewed: 19 July 2025
Paula
United StatesBar only open until 7
Loved the pools
Stayed in July 2025
Reviewed: 18 July 2025
Elaine
United StatesNothing!
It was peaceful and absolutely beautiful! The best place in the keys to stay!
Stayed in June 2025
Reviewed: 18 July 2025
Elizabeth
United StatesGreat location. Room was clean and comfortable. The patio was gorgeous. The staff were great
Stayed in July 2025
Reviewed: 18 July 2025
Darice
United StatesNothing!
The room was spacious with high ceilings, a vanity, and gorgeous walk in shower. Bed was comfortable and decor stylish. The pool/bar area was so cute and the breakfast that was included was so delicious with unique options like cheesy grits and deviled eggs, the best Belgian waffles and even energy shots of ginger and turmeric. Staff was very courteous, especially the bartender. Included in our welcome folder was a pirates coin for two free drinks! The foliage around the bungalows was gorgeous, with jasmine trees in bloom and various palms and ferns, so lush and tropical! Our bungalow was in a cool, antique home that had a huge front verandah with wicker chairs and couches.
Stayed in July 2025
Reviewed: 16 July 2025
Matheus
BrazilJust the bed was not so comfortable.
Excellent location, incredible staff and very good facilities at the hotel.
Stayed in July 2025
Reviewed: 15 July 2025
Bryan
United StatesI wish the hotel bar could stay open later.
The serenity of the environment. As well, its location to multiple sites was a bonus.
Stayed in July 2025
Reviewed: 14 July 2025
Gary
United KingdomThere was nothing to not like
From the welcome in reception to the wonderful bungalow to Kirk who ran the bar and the guests around the bar everything was wonderful. Location two blocks from Duval Street so easy to walk to bars and restaurants and sights such as Hemingway’s.
Stayed in July 2025
Reviewed: 11 July 2025
Julius
United StatesRoom could really have used a comfortable chair in the corner
Great location! An oasis in Old Town Key West but walkable everywhere. Lovely, lush grounds. 3 pools. Wonderful staff! Beautiful room! Clean and spacious!
Stayed in June 2025
Reviewed: 8 July 2025
Rebecca
United StatesNothing was disliked. Maybe add some island drum music around the pool. Although it was peaceful and enjoyable.
Tropical, historic and tranquil. Just a few blocks walk from Duval Street. Several different parking lots. The resort feels large without being spread out too far getting around. We were very close to pools and breakfast.
Stayed in July 2025
Reviewed: 2 July 2025
John
United KingdomThe breakfast offering is limited but that is us being really picky.
The room, the feel of the hotel and staff made this hotel an ideal place to stay in Key West. The location is also ideal with a short everything being a short walk away, whilst being peaceful and quiet.
Stayed in July 2025
Reviewed: 1 July 2025
Crow
United StatesThe lights in the room are very pretty. It wasn't as bright as I would have liked at times. During the daytime, it is not a problem because the windows let in plenty of natural light.
The rooms are cozy, and they have everything you need. They are clean and modern with some vintage touches. There is under-bed storage instead of a traditional dresser. We were very comfortable with the room. Each room has a little sitting area outside the room or close by. It is beautiful and lush. The grounds of Winslow's Bungalows are like a movie. The various trees and plants are gorgeous. It is a tropical paradise. There are many iguanas and chameleons all over the property. It was magical. The entire island is four by two miles. The bungalows are in the center, so it is easy to get to everything on foot. We rented a golf cart for two days when we went to Fort Zachary beach- just so we wouldn't have to carry everything.
Stayed in June 2025
Reviewed: 29 June 2025
Elena
United KingdomAbsolutely nothing, everything is perfect.
These bungalows are absolutely fantastic! Super chic and located in a quiet and safe area, close to the high street. We couldn’t have found a better place.
Stayed in June 2025
Reviewed: 28 June 2025
Samantha
United KingdomThe main pool was closed and room albeit gorgeous, was quite dark.
Gorgeous hotel. Exceeded expectations. Loved that it was such an oasis of nature. The perfect Key West experience.
Stayed in June 2025
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