Kimpton Winslow's Bungalows

Key West, Florida Keys

Virgin rating

The hotel

Set less than a mile from the Southernmost Point of the US, you’ll feel at home in these fresh, beautifully landscaped bungalows in the heard of Old Key West. This sliver of an island is far far away from your daily schedule, delivering relaxation, open air bars, and cute vintage shopping – all on the hotels doorstep. Spend your days snorkelling off the idyllic coast, or relaxing with a famous Rum Runner from the poolside Bungalow bar – it won’t take you long to get into the pace of island life at all!

Amenities

  • Bicycle Rental
  • Free Breakfast
  • Bar
  • Internet Access
  • Safety Deposit Box
  • Swimming Pool

Where is it

Located in Key West, Florida, 800 yards from Duval Street and 0.6 miles from the Southernmost Point. 

Hotel information

85 guestrooms, all with air conditioning, mini fridge, HDTV, bathroom amenities, safe, hairdryer, bath robe, yoga mat, and complimentary WiFi access. 

Essential Rooms have either 1 king-size bed, 1 queen-size bed, or 2 queen-size beds, sleeping maximum 4 people. 

Essential Balcony rooms feature a patio or balcony, with 1 king-size bed, sleeping maximum 2 adults.

Premium Rooms with Sofa bed feature 1 king-size bed, plus a sofa bed, sleeping maximum 3 adults.

Premium Rooms with Soaking tub feature a separate walk-in shower and bath tube, with 1 king-size bed plus a sofa bed, sleeping maximum 3 adults.  

Complimentary continental breakfast served daily. Bungalow Bar (outdoor pool bar with daily happy hour). Dogs and People food cart (serving light fare). 

3 outdoor swimming pools. Bicycle rental*. Discounted spa services available at Prana Spa*. 

Complimentary WiFi access. Concierge. Self-parking $20 plus tax per day (payable locally, fee subject to change).

There is an amenity fee of $35 plus tax per room per night (payable locally, fee subject to change). 

Fee includes:- Complimentary continental breakfast, coffee and tea service – Complimentary WiFi access – Boozy welcome arrival drink – Snorkel kit with mask and snorkel – Boating towels – Afternoon poolside refresher – Complimentary local and toll free phone calls – Pool access and pool towels – Access to Press Reader on your smart device featuring over 7,000 newspapers and magazines. Resort fee and inclusions are subject to change and availability. 

*Denotes local charge. 

Rating summary

  • Location Image of the Tripadvisor rating
  • Sleep Quality Image of the Tripadvisor rating
  • Rooms Image of the Tripadvisor rating
  • Service Image of the Tripadvisor rating
  • Value Image of the Tripadvisor rating
  • Cleanliness Image of the Tripadvisor rating

Traveller rating

  • Excellent (254)
  • Very good (40)
  • Average (30)
  • Poor (23)
  • Terrible (33)
Image of the Tripadvisor rating I wish I had read the reviews first

Apr 13, 2024 Maude B

I wish I had read the reviews before we went to Winslow's Bungalows. So it's good that you are doing so now. We unfortunately had a very disappointing stay, and paid over $600/night. We booked a King Patio, and it's hard to describe how small the room was other than that my husband and I had to each step aside when the other wanted to walk… Read more
I wish I had read the reviews before we went to Winslow's Bungalows. So it's good that you are doing so now. We unfortunately had a very disappointing stay, and paid over $600/night. We booked a King Patio, and it's hard to describe how small the room was other than that my husband and I had to each step aside when the other wanted to walk anywhere in the room. There was not any drawers for clothing or even a luggage rack. So my suitcase went on the floor in the corner and had to be closed anytime we wanted to walk around the bed. And my husband had to keep his closed and upright in front of the door, and open it up on the bed anytime he wanted to access his clothes. So, TINY. The bathroom was similarly tiny. The sink was the size of a shoe box, no I'm not exaggerating. And again, no shelving to place anything, so we had to put our toothbrushes, etc on the back of the toilet. Aside from the room, housekeeping never came to our room, even though their supply cart, with a long dirty duster sticking out, had been sitting outside our room since 9:00am every morning. As for the grounds, they are pretty, but tired. We mistakenly thought that Kimpton still owned the property, as some of the online listings still had the Kimpton name and logo connected to the property. But it seems that since they sold the property, very little maintenance has been done. Honestly, a Hampton's Inn would have been nicer, bigger and cleaner, for about 1/4 of the price. Read less
Image of the Tripadvisor rating Key West hidden paradise

Apr 12, 2024 Nikki M

An absolute beautiful property in Key West. The grounds, the pools and the rooms are all fabulous. Breakfast was amazing and we loved the different smoothie options each day, the waffles are also to die for. Shoutout to Mike for the tasty breakfast options. The staff members are all nice and everyone smiles in passing. Lemi is amazing at her… Read more
An absolute beautiful property in Key West. The grounds, the pools and the rooms are all fabulous. Breakfast was amazing and we loved the different smoothie options each day, the waffles are also to die for. Shoutout to Mike for the tasty breakfast options. The staff members are all nice and everyone smiles in passing. Lemi is amazing at her job. She is so hospitable and helpful. You can tell she takes pride in how the property looks. It was our 2 year anniversary and the staff helped surprise me by putting the most gorgeous flowers I have ever seen in our room. The concierge Jenni perfectly organized this. From check in to check out with Sonia at the Front Desk everything here is an absolute dream. Thank you all for the wonderful week in paradise. Read less
Image of the Tripadvisor rating Amazing spot!

Apr 6, 2024 Toby B

5+ stars! One of the nicest places I've stayed! Loved ever minute! We stayed in April 2022. The grounds and facilities were amazing! Can't wait to go back! Very easily walkable to everything you works want to see in Key West! Breakfast was a great variety.
Image of the Tripadvisor rating Can’t recommend now has left IHG / dropped Kimpton

Mar 25, 2024 gilby_paul York, United Kingdom

Interesting hotel. Little huts for each room which was quite qwerky. Rooms had a little musty smell but assume that’s due to the wooden structure. Rooms clean and fresh. Felt slightly overpriced in general. Breakfast supplied is on the poor side, not much to say here because not much was offered. One good thing about this hotel is that it used to… Read more
Interesting hotel. Little huts for each room which was quite qwerky. Rooms had a little musty smell but assume that’s due to the wooden structure. Rooms clean and fresh. Felt slightly overpriced in general. Breakfast supplied is on the poor side, not much to say here because not much was offered. One good thing about this hotel is that it used to be a Kimpton and part of IHG but seems recently the owners have pulled it from the brand. Won’t be staying here again with dropping IHG as that was the only main appeal / pull to here for me for the perks and ability to use points etc for stay. Read less
Image of the Tripadvisor rating Great spot, but dont go for the breakfast

Mar 23, 2024 DanS123456789012 Las Vegas, Nevada

This hotel is definitely made for those travelling as a couple or solo. I would not stay here if this was a friend trip and you had to share a room. That said the rooms were very nicely kept. On the smaller size, so don't expect your typical hotel size room. The bathroom seemed cramped but workable. I don't say any of this with negative… Read more
This hotel is definitely made for those travelling as a couple or solo. I would not stay here if this was a friend trip and you had to share a room. That said the rooms were very nicely kept. On the smaller size, so don't expect your typical hotel size room. The bathroom seemed cramped but workable. I don't say any of this with negative connotations just something to be aware of. The breakfast was the worst part of stay, it was truly just bagels and hardboiled eggs. For the price of the stay I would have expected a little but more. The grounds were well-kept and orderly. I personally loved the hammock in a secluded area to read my book. The front desk attendant was very helpful in guiding me to some dining places. Read less