Winslow's Bungalows

Key West, Florida Keys

Star rating

2 Queen Essential Room
Bungalow Bar
Essential Room with Patio
1 King Premium with Sofa Bed
1 King Premium with Sofa Bed
2 Queen Essential Room
Bungalow Bar
Essential Room with Patio
1 King Premium with Sofa Bed
1 King Premium with Sofa Bed

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 (325)
  • Very good (44)
  • Average (35)
  • Poor (26)
  • Terrible (37)
Image of the Tripadvisor rating 10/10 would come back here!

Jul 18, 2025 daricegall Branford, Connecticut

This is such a beautiful property! Location is perfect, walkable to Duval Street and Mallory Square. Room was in a gorgeous mansion, spacious, adorable vanity with a huge shower! Loved the delicious breakfast with really unique offerings.
Image of the Tripadvisor rating Well needed Vacation and it was.... Amazing

Jul 10, 2025 Claudia M

We enjoyed everything about Winslow Bungalows, it was centrally located to everything ,so we could walk everywhere. Very clean, staff was welcoming throughout the property. Our Bungalow was very clean, bed was great. We used the pool by the bar, that was nice had local musicians playing thru out the day. Our Bartender Keith was great.
Image of the Tripadvisor rating Cute but not Quiet

Jul 6, 2025 Lindsey J Franklin, Tennessee

The Winslow's Bungalows are a super cute property and located in walking distance to many main attractions in Key West. It seems our room - a Winslet - had very thin walls and we could hear the conversations of the guests next to us. Housekeeping is done daily, which is very nice after a being out and about in the heat and humidity.
Image of the Tripadvisor rating FABULOUS

Jul 5, 2025 AnnMarie M

To start, Sonia at the front desk is not only super friendly and professional, she is so attentive and accommodating to the guests. I give a 5 Star to the Winslow. From the very clean room, pool area, fabulous breakfast (included), entertainment, landscaping and staff. Will make this my always future go to in Key West. Thank you so much 😊
Image of the Tripadvisor rating Depends on the room you are allocated !

May 14, 2025 Karen C

In the main the Winslow bungalows are lovely. The surrounding greenery and oasis feel was great. My biggest issue was the room (41) this room had no windows and no natural light. The air conditioning unit had seen better days and was extremely noisy. Making it hard to sleep. The only source of light was a glass door which had slatted thick wooden… Read more
In the main the Winslow bungalows are lovely. The surrounding greenery and oasis feel was great. My biggest issue was the room (41) this room had no windows and no natural light. The air conditioning unit had seen better days and was extremely noisy. Making it hard to sleep. The only source of light was a glass door which had slatted thick wooden blinds . The bathroom was so small it was hard to store any toiletries , we had to use the floor! A little disappointed as I feel that if you receive this room you have been short changed!!! Read less