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Kimpton Winslow's Bungalows

725 Truman Ave, Key West, FL 33040-6423
COVID-19 update: See the added health and safety measures this property is taking.Read more
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USD 511
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Prices are provided by our partners, and reflect total costs of the stay, including all taxes and fees known to our partners. Please see our partners for more details.
Payments made by partners impact the order of prices displayed. Room types may vary.
Traveller (269)
Panoramas (7)
Room & Suite (79)
What is Travellers’ Choice?
Tripadvisor gives a Travellers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.
Payments made by partners impact the order of prices displayed. Room types may vary.
Travel safe during COVID-19
Visit our Travel Safe hub to see how we're helping you make more informed travel decisions during COVID-19.
What you can expect during your stay
  • Hand sanitiser available to guests & staff
  • Regularly sanitised high-traffic areas
  • Staff required to regularly wash hands
Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.


#19 of 53 hotels in Key West
Travellers' Choice
Winslow's Bungalows spans a lush, landscaped campus in the heart of Old Town. Named for famous painter and summer resident Winslow Homer, this expansive haven boasts three private pools, an outdoor bar and vibrant gardens. It’s an idyllic scene for couples, families, groups and wedding parties. Key West is a one-of-a-kind island, and Kimpton Key West gives you five authentic ways to enjoy the carefree fun. Fanning across the heart of Old Town, our diverse collection of historic buildings each has its own tale to tell—and its own unique offerings. From the low-key luxury of Ridley House to the quiet, expansive experience of Winslow’s Bungalows, there’s truly something for every mood. Tying them all together are bohemian style, glimmering pools, lush gardens—and Kimpton hospitality that is as warm as sunshine on a palm frond. We invite you to discover the Kimpton Key West hotel that fits you best, and escape to this land (and sea) of pure enchantment.
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Property amenities
Paid private parking on-site
Free High Speed Internet (WiFi)
Free breakfast
Baggage storage
Pool / beach towels
Outdoor pool
Fence around pool
Breakfast buffet
Non-smoking hotel
Outdoor furniture
Picnic area
Sun loungers / beach chairs
Sun terrace
Sun umbrellas
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Room features
Air conditioning
Private balcony
Flatscreen TV
Bath / shower
Complimentary toiletries
Wake-up service / alarm clock
Hair dryer
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Room types
Non-smoking rooms
Good to know
Languages Spoken
English, Spanish
213Reviews39Q+A33Room tips
Traveller rating
  • 160
  • 24
  • 13
  • 7
  • 9
Time of year
Traveller type
Selected filters
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  • English
Popular mentions
mjrgnsn wrote a review 21 Jan
Ocala, Florida635 contributions61 helpful votes
Staff were super welcoming. Loved the paths that wound there way through the property. Smaller rooms. Ours was on a second florr in a older home with a balcony that over looked the street. If not familiar with Key West, the roosters do wake up around 2 AM and crow through the night for a fyi, but you get used to it. If you have issues with stairs or have special needs, be sure to call ahead. Everything was perfect for us and the rooms and property were well appointed. Loved our stay and walked everywhere from the Southern Most Point, to Mallory Square to take in the sunset, and points in-between.
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Date of stay: January 2022
Room Tip: Call ahead if you have special needs.
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vjack0887 wrote a review 17 Jan
Houston, Texas127 contributions79 helpful votes
This is a contemporary hotel and the design is awesome. The grounds, pools, and outdoor areas are beautiful. The hotel was slightly delayed in getting me checked in at 4pm, however, I was provided an opportunity to change in a common restroom, leave my luggage at the check-in office, and enjoy the bar or amenity areas. They did inform me upon check-in that the hotel was not offering cleaning services of the hotel room during the stay due to COVID. I did request additional towels during my stay and they were brought to my room within 10 minutes of my request. My room was on the 2nd floor of a building, room #44. The building had a common entry on the ground floor and an interior staircase that lead to the room. Room #44 was small, basically an efficiency, but worked perfect for me. The room was equipped with an HVAC unit, a door leading to a common area balcony and seating area, a small mini fridge, ice bucket, glasses, hair dryer, and two robes. The room also had shampoo, body wash, conditioner, soap, and body lotion. The bed was comfortable, the pillows were very soft. The TV had basic cable and the free internet did work well throughout my stay. The management area had small snacks for sale and bottles of wine for $15 each. The hotel bar was open from 12pm - 7pm daily. I had several great drinks at the hotel bar. They do not allow you to charge the drinks to the room. All drinks must be paid for and closed our daily. The hotel breakfast included bagels, hard boiled eggs, pastries, cereals, muffins, yogurt, bananas, oranges, coffee and tea. If you are looking for a "hot" breakfast you will need to go out to brunch. The location is great. I was able to walk to several really great restaurants. I did not rent a car, golf cart, or scooter, but there are plenty of options to do so around the hotel if you choose. I had no trouble getting an Uber to or from this location throughout my stay. The hotel does offer bikes, but I didn't use one during my stay. The pools were beautiful and the gardens throughout the property are really beautiful. I saw a review about the roosters. I wanted to address this as a guest as I was nervous about this when I booked. The chickens and roosters are EVERYWHERE on the island. No matter where you stay you will hear, and see, them. Yes, they did wake me up at 2am. Yes, they are annoying, but it seems there is no escape from them and it is no reason not to stay at this location. I walked a good portion of the island and went to all three beaches. Don't waste your money on an ocean view. You will have plenty of time to be on the water. This is a great spot with good service. Pluses: Location, grounds, and room design
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Date of stay: January 2022
Sleep Quality
MOHAMMED wrote a review 9 Jan
Miami, Florida12 contributions16 helpful votes
I booked a king room with patio for a birthday trip. A chair in front of the door facing a parking lot is not a patio. I asked for a nicer room and was told they all have "patios" in front or shared spaces with other rooms. There was constant noise from the room upstairs and trucks and cars in the morning. The property overall is a lush oasis but my room was very disappointing. Average size and no tub, only shower. On a positive note, staff was polite attentive through text and the property is well-kept. Great location within walking distance to everything, but the main street it's on is a bit busy and noisy. Pools are small but mostly quiet and well-stocked with towels, and there are three pools to choose from. Welcome drink was a nice touch and we were also offered complimentary sparkling wine for the birthday. Bed was comfortable as well. No turndown service due to "COVID" at this point is unacceptable for the price. You don't get COVID from cleaning an empty room.....enough already. Very disappointing room compared to my previous stay at the Kimpton Ella's Cottages. Normally love Kimpton properties but would not really recommend Bungalows. There are better options for this price point.
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Date of stay: January 2022
1 Helpful vote
beautifulamerica wrote a review 8 Jan
2 contributions
Absolutely gorgeous grounds & quintessential Key West property! Staff is wonderful! Huge shout out to Laura & another front desk girl that went above and beyond to make our stay wonderful. Rooms are eclectic and sweet. Bathroom is small, but there is a vanity in the room, which made the bathroom size non issue for us.
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Date of stay: January 2022Trip type: Travelled as a couple
pmckenney32 wrote a review 5 Jan
Charlotte, North Carolina3 contributions1 helpful vote
Kimpton has done a great job here. Everything about this place is fantastic. Beautiful property with updated rooms. Patrick at the front desk could not have been more helpful and professional. Bartenders were very friendly. I’ll be back to Winslow’s.
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Date of stay: January 2022Trip type: Travelled as a couple
1 Helpful vote
USD 204 - USD 515 (Based on Average Rates for a Standard Room)
chelsea house pool & gardens hotel key west, chelsea house pool and gardens
Key Lime Inn
United StatesFloridaFlorida KeysKey West
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Frequently Asked Questions about Kimpton Winslow's Bungalows
Which popular attractions are close to Kimpton Winslow's Bungalows?
Nearby attractions include Saint Mary Star of the Sea (0.1 km), Key West Firehouse Museum (0.3 km), and The Cabaret At La Te Da (0.4 km).
What are some of the property amenities at Kimpton Winslow's Bungalows?
Some of the more popular amenities offered include free wifi, free breakfast, and a pool.
Which room amenities are available at Kimpton Winslow's Bungalows?
Top room amenities include air conditioning, a flat screen TV, and a refrigerator.
What food & drink options are available at Kimpton Winslow's Bungalows?
Guests can enjoy free breakfast during their stay.
Is parking available at Kimpton Winslow's Bungalows?
Yes, paid private parking on-site is available to guests.
What are some restaurants close to Kimpton Winslow's Bungalows?
Conveniently located restaurants include Key West Cuban Coffee shop, Better Than Sex - A Dessert Restaurant Key West, and El Siboney Restaurant.
Are there opportunities to exercise at Kimpton Winslow's Bungalows?
Yes, guests have access to a pool during their stay.
Is Kimpton Winslow's Bungalows located near the city centre?
Yes, it is 0.5 km away from the centre of Key West.
Which languages are spoken by the staff at Kimpton Winslow's Bungalows?
The staff speaks multiple languages, including English and Spanish.
Are there any historical sites close to Kimpton Winslow's Bungalows?
Many travellers enjoy visiting Curry Mansion Inn (1.0 km), Key West Garden Club (1.3 km), and Harry S. Truman Little White House (1.1 km).
Is Kimpton Winslow's Bungalows accessible?
Yes, it offers reduced mobility rooms. For specific enquiries, we recommend calling ahead to confirm.