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  5. Reviews of Winslow's Bungalows - Key West Historic Inns

Reviews of Winslow's Bungalows - Key West Historic Inns 4 stars

725 Truman Avenue, Downtown Key West, Key West, FL 33040, United States

#34 of 51 B&Bs and Inns in Key West

Guests' Choice

Review score

Based on 872 hotel reviews

8.6

Score breakdown

  • Cleanliness

    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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Showing 1 – 25

  • Reviewed: 1 September 2025

    10
    My day at winds low was relaxing super fun thank you we definitely coming back
    • Leisure trip
    • Couple
    • Key Lime
    • Stayed 2 nights
    • Submitted via mobile

    To 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

    10
    Exceptional
    • Leisure trip
    • Couple
    • Maloney King
    • Stayed 5 nights
    • Submitted via mobile

    Very relaxing 😎

    Very peaceful ☺️

    Stayed in August 2025

  • Reviewed: 22 August 2025

    8.0
    Very relaxing, friendly & accommodating staff.
    • Leisure trip
    • Couple
    • Key Lime
    • Stayed 3 nights
    • Submitted via mobile

    Location

    Stayed in August 2025

  • Reviewed: 22 August 2025

    10
    Fantastic place to stay easy access to everything we loved it here x
    • Leisure trip
    • Couple
    • Winslet
    • Stayed 7 nights
    • Submitted via mobile

    Nothing

    Everything was perfect

    Stayed in August 2025

  • Reviewed: 18 August 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Winslow
    • Stayed 4 nights
    • Submitted via mobile

    Location, common areas, room

    Stayed in August 2025

  • Reviewed: 13 August 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Key Lime
    • Stayed 2 nights
    • Submitted via mobile

    Staff were unreal, could not have been more helpful, Buffett breakfast was amazing, great selection

    Stayed in August 2025

  • Reviewed: 5 August 2025

    10
    Beautiful Hotel for holiday in tropical paradise.
    • Leisure trip
    • Couple
    • Annex
    • Stayed 4 nights
    • Submitted via mobile

    Water 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

    10
    ❤️
    • Leisure trip
    • Couple
    • Winslow
    • Stayed 4 nights
    • Submitted via mobile

    Beautiful place

    Stayed in July 2025

  • Reviewed: 26 July 2025

    9.0
    facilities and location was convenient and had everything we wanted to make our stay fantastic!
    • Leisure trip
    • Couple
    • Winslow Mobility
    • Stayed 3 nights
    • Submitted via mobile

    Room 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

    10
    Exceptional
    • Leisure trip
    • Couple
    • Winslow
    • Stayed 1 night
    • Submitted via mobile

    Pet friendly

    Stayed in May 2025

  • Reviewed: 23 July 2025

    10
    Perfect! Will be back!
    • Business trip
    • Couple
    • Winslow
    • Stayed 3 nights

    N/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

    9.0
    Great stay! Close to town bit nice and quiet at the resort
    • Leisure trip
    • Couple
    • Winslet
    • Stayed 4 nights
    • Submitted via mobile

    Bar only open until 7

    Loved the pools

    Stayed in July 2025

  • Reviewed: 18 July 2025

    10
    Tranquility and peace
    • Leisure trip
    • Couple
    • Winslet
    • Stayed 2 nights
    • Submitted via mobile

    Nothing!

    It was peaceful and absolutely beautiful! The best place in the keys to stay!

    Stayed in June 2025

  • Reviewed: 18 July 2025

    10
    Can’t wait to go back
    • Leisure trip
    • Couple
    • Winslet
    • Stayed 4 nights

    Great location. Room was clean and comfortable. The patio was gorgeous. The staff were great

    Stayed in July 2025

  • Reviewed: 18 July 2025

    10
    Stylish, charming, and beautiful bungalows! Loved, loved, loved this place!
    • Leisure trip
    • Couple
    • Winslow
    • Stayed 1 night
    • Submitted via mobile

    Nothing!

    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

    9.0
    Amazing
    • Leisure trip
    • Couple
    • Winslet
    • Stayed 3 nights
    • Submitted via mobile

    Just 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

    9.0
    Beautiful, serene property designed for a romantic getaway, but locationally positive
    • Leisure trip
    • Couple
    • Bungalow
    • Stayed 3 nights
    • Submitted via mobile

    I 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

    10
    Stay here. You will be amazed
    • Leisure trip
    • People with friends
    • Winslow
    • Stayed 3 nights
    • Submitted via mobile

    There 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

    10
    A lovely oasis in Key West!!
    • Leisure trip
    • Solo traveller
    • Winslet
    • Stayed 7 nights
    • Submitted via mobile

    Room 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

    10
    I never stay the same place twice, however this may be the first time that I might change my mind!
    • Leisure trip
    • Couple
    • Winslow
    • Stayed 3 nights
    • Submitted via mobile

    Nothing 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

    10
    Superb.
    • Leisure trip
    • Family with young children
    • Truman King Patio
    • Stayed 1 night

    The 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

    10
    Winslow's Bungalows are magical.
    • Leisure trip
    • Couple
    • Annex
    • Stayed 7 nights

    The 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

    10
    We had three fabulous days at Winslow’s Bungalows, starting with a very healthy breakfast with vegan and vegetarian opti
    • Leisure trip
    • Couple
    • Key Lime
    • Stayed 3 nights
    • Submitted via mobile

    Absolutely 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

    10
    Exceptional
    • Leisure trip
    • Couple
    • Key Lime
    • Stayed 2 nights
    • Submitted via mobile

    The 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

Showing 1 – 25

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