Experience Paradise: Kimpton Winslow’s Bungalows in Key West

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Kimpton Winslow’s Bungalows is the perfect place to stay for a relaxing getaway. Located in the heart of Old Town in Key West, Florida, this boutique hotel offers everything you need for an unforgettable vacation.

It’s part of the Kimpton Hotels & Restaurants group which is owned by IHG (Intercontinental Hotel Group). This unique property offers the perfect combination of paradise-like surroundings and world-class amenities. 

Palm trees in front of a white building and white picket fence.

Going to Key West for the first time, we wanted to stay in the center of Old Town Key West so that we could be close enough to walk to most of the top attractions.

Winslow’s Bungalows not only fit the bill but also provides so much more. The hotel is comprised of several historic properties that are surrounded by cute little picket fences. Overall, the property reflects a modern bohemian style while retaining the historic character surrounded by lush gardens.

Outdoor sofa beneath a large tree.
White and green swing beneath a large tree.

Guest Rooms

Bungalow number 86 surrounded by lush vegetation.

The guest rooms are equipped with all the comforts of home so that you can truly relax during your stay.

Bedroom and bathroom inside of a bungalow.

The accommodations at Kimpton Winslow’s Bungalows feature plush bedding with down pillows, stylish décor, and amenities such as flat-screen TVs with cable channels (you’ll appreciate not having to log into your apps to watch tv), free wi-fi, and refrigerators. The only thing we missed having in the room was a safe.

The bathrooms have plenty of space and come stocked with toiletries from Atelier Bloem.


There are three outdoor pools surrounded by tropical landscaping. 

Swimming pool with lounge chair and umbrellas.
Swimming pool with lounge chairs.

Other amenities include Turkish robes, in-room yoga mats, an umbrella (you never know when it might rain, right?), and an onsite concierge.

Guests of Kimpton Winslow’s Bungalows are also welcome to take advantage of some of the unique experiences the hotel offers. These include complimentary bike rentals (you will have to provide a credit card to use them), aqua yoga, absinthe tasting, and local live music.

The hotel offers a complimentary continental breakfast with fruit, yogurt, cereal, oatmeal, bagels, and coffee, and there are a variety of restaurants in the area for lunch and dinner. The on-site bar, Bungalow’s, is located by one of the pools and is open from noon until dusk, offering a selection of cocktails, wine, and beers, such as their famous Rum Runner.

Outdoor bar at a resort.

Guests of Kimpton Key West are charged a $35 (plus tax) per day guest amenity fee. While we’re not an advocate for additional fees, at least at this hotel you actually get something in return.

Cayo Hueso Passion Fruit Shandy cans.
Welcome drink.

The fee allows for complimentary breakfast, wifi, a boozy welcome arrival drink, an afternoon poolside refresher, pool access and towels, and the use of a snorkel kit.

Sign telling guests to let the hotel know if you need something.

Missing something? They’ve got you covered. We like to wake up early and enjoy a cup of freshly brewed coffee. Since breakfast is not served until 8:00 am, we were able to get a coffee maker placed in our room along with K-cups.

Keurig coffee maker, paper coffee cups, bottles of water, and K-cups.

Pet Friendly

Like all of the other Kimpton properties, Winslow’s Bungalow is a pet-friendly property. Let them know in advance about your special companion. Pets stay free at the hotel and are provided pet beds, water bowls, and custom Kimpton dog treats. 

Dog waste station with dog waste bags in front of a white building.

Nearby Points of Interest

The hotel, which gets its name from a summer resident and famous painter, is situated in a premier location, just minutes away from popular attractions such as Duval Street (3 blocks), Mallory Square (1.1 miles), and Fort Zachary Taylor State Park (0.8 miles). The nearby beach at the state park also provides an idyllic setting for many activities, whether you wish to spend your days sunbathing, swimming, or snorkeling. 

Sign with directions and distances to locations around the globe from Key West.

While being close to the main attractions of Key West, its location near St. Mary’s Basilica provides a quiet and peaceful atmosphere. This is further enhanced by the hotel’s tropical landscaping which adds to its charm. It truly is a slice of paradise. 

Man and woman standing in front of the Southernmost Point buoy.

Other nearby attractions include:

  • Ernest Hemingway House, 0.4 miles
  • Bahama Village, 0.4 miles
  • Butterfly Conservatory, 0.5 miles
  • Southernmost Point, 0.6 miles
  • Sloppy Joe’s, 0.9 miles
  • Mel Fisher Maritime Museum, 1.0. mile


The check-in time is 4:00 pm and check-out is 11:00 am. IHG One Rewards members have the possibility of having their check-out time extended to 2:00 pm, subject to availability.

Entrance to the lobby at Winslow's Bungalows.


Parking is limited all over the island, and the hotel is no exception. On-site parking is available at the rate of $30 + tax per day.

Overall, Kimpton Winslow’s Bungalows is an ideal destination for those seeking luxury accommodations with modern amenities and gorgeous surroundings. The property offers something for everyone, from the active traveler to those looking for some rest and relaxation. Whether you’re planning a romantic getaway or a family vacation, Kimpton Winslow’s Bungalows is sure to provide lasting memories. 

Kimpton Boutique Hotels

Kimpton has 5 boutique properties in Key West: 

  • Winslow’s Bungalow’s – The largest property in the collection, Winslow’s Bungalows is comprised of 85 rooms and is located on Truman Avenue and Elizabeth Street near the quieter end of Duval Street.
  • Ridley House – An adult-only property, there are 23 rooms at 601 Caroline Street, just 2 blocks from the harbor.
  • Ella’s Cottages – The smallest property in the group, there are 22 rooms at the location on Simonton Street, one block away from Duval. This property is conveniently located on a stop at the free Duval Loop.
  • Lighthouse Hotel – Located next to the Lighthouse Museum, this property is closest to the Hemingway House and Fort Zachary State Park. There are 45 rooms with accommodation options ranging from an essential queen room to their famous Hemingway Suite.
  • Fitch Lodge – Previously Albury Court, this location has 44 rooms and is close to the harbor and Harpoon Harry’s.


Winslow’s Bungalows is located at 725 Truman Avenue, Key West, Florida.

We enjoyed Kimpton’s Southern hospitality and how well they kept in touch with their guests (us!) via text. We would definitely consider staying at one of their Key West properties for future trips.

Leave us a comment below letting us know what your favorite Kimpton property is.

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  1. looking for 1 night. 3 adults possibly Jan 23rd.
    what do you have available.
    my wife and I have stayed several times in key west going back almost 50 years ago camping at Boyds but not familiar with your resorts
    thank you

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