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

Reviews of Winslow's Bungalows - Key West Historic Inns This rating is a reflection of how the property compares to the industry standard when it comes to price, facilities and services available. It's based on a self-evaluation by the property. Use this rating to help choose your stay!

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

    7.9

  • Free Wifi

    8.5

Verified guest reviews from real Bookers

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Showing 1 - 25

  • Reviewed: September 5, 2025

    8.0
    We had a lovely time. Most likely we may return there.
    • Leisure trip
    • Group
    • Winslet
    • Stayed 4 nights
    • Submitted from a mobile device

    Pool. Small. Not enough chairs. Lol roosters at 5a.

    Ample parking. Clean manicured grounds. Music at bar was nice. The AM breakfast bar was nice. It was historic and i liked that. Our room was spacious and clean.

    Stayed in September 2025

  • Reviewed: September 4, 2025

    10
    amazing
    • Leisure trip
    • Couple
    • Key Lime
    • Stayed 2 nights

    nothing

    property was very cozy, very centrally located to Duval St. close to restaurants, bars, etc. Breakfast was good. private parking staff was very helpful i will comeback for sure.

    Stayed in August 2025

  • Reviewed: September 3, 2025

    10
    amazing!!
    • Leisure trip
    • Travelers with friends
    • Winslow
    • Stayed 3 nights
    • Submitted from a mobile device

    nothing, everything was perfect

    the breakfast was my favorite part and they did little events the whole time we were there

    Stayed in August 2025

  • Reviewed: September 2, 2025

    10
    Exceptional
    • Leisure trip
    • Group
    • Key Lime
    • Stayed 2 nights
    • Submitted from a mobile device

    Lovely feel, two pools.

    Stayed in July 2025

  • Reviewed: September 2, 2025

    9.0
    Excited to return for a 3rd time
    • Leisure trip
    • Couple
    • Treehouse Suite
    • Stayed 1 night
    • Submitted from a mobile device

    Breakfast and water pressure should be improved (very light shower and took 30-40 minutes to run a bath) but otherwise an excellent stay. Would be great to have the bar open until later.

    Excellent location, lovely staff, and cute rooms. Our second trip and it seems rooms gave been thoughtfully refreshed. Wonderful bed and pillows. Great vibe and lush older growth plants historic grounds.

    Stayed in September 2025

  • Reviewed: September 1, 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 from a mobile device

    To be honest the food I don’t eat cold food

    I love the location walkable and very relaxing

    Stayed in August 2025

  • Reviewed: August 29, 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Maloney King
    • Stayed 5 nights
    • Submitted from a mobile device

    Very relaxing 😎

    Very peaceful ☺️

    Stayed in August 2025

  • Reviewed: August 22, 2025

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

    Location

    Stayed in August 2025

  • Reviewed: August 22, 2025

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

    Nothing

    Everything was perfect

    Stayed in August 2025

  • Reviewed: August 18, 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Winslow
    • Stayed 4 nights
    • Submitted from a mobile device

    Location, common areas, room

    Stayed in August 2025

  • Reviewed: August 13, 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Key Lime
    • Stayed 2 nights
    • Submitted from a mobile device

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

    Stayed in August 2025

  • Reviewed: August 5, 2025

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

    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: July 31, 2025

    10
    ❤️
    • Leisure trip
    • Couple
    • Winslow
    • Stayed 4 nights
    • Submitted from a mobile device

    Beautiful place

    Stayed in July 2025

  • Reviewed: July 26, 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 from a mobile device

    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: July 23, 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Winslow
    • Stayed 1 night
    • Submitted from a mobile device

    Pet friendly

    Stayed in May 2025

  • Reviewed: July 23, 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: July 19, 2025

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

    Bar only open until 7

    Loved the pools

    Stayed in July 2025

  • Reviewed: July 18, 2025

    10
    Tranquility and peace
    • Leisure trip
    • Couple
    • Winslet
    • Stayed 2 nights
    • Submitted from a mobile device

    Nothing!

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

    Stayed in June 2025

  • Reviewed: July 18, 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: July 18, 2025

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

    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: July 16, 2025

    9.0
    Amazing
    • Leisure trip
    • Couple
    • Winslet
    • Stayed 3 nights
    • Submitted from a mobile device

    Just the bed was not so comfortable.

    Excellent location, incredible staff and very good facilities at the hotel.

    Stayed in July 2025

  • Reviewed: July 15, 2025

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

    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: July 14, 2025

    10
    Stay here. You will be amazed
    • Leisure trip
    • Travelers with friends
    • Winslow
    • Stayed 3 nights
    • Submitted from a mobile device

    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: July 11, 2025

    10
    A lovely oasis in Key West!!
    • Leisure trip
    • Solo traveler
    • Winslet
    • Stayed 7 nights
    • Submitted from a mobile device

    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

Showing 1 - 25

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