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.
Based on 463 reviews
Rating summary
Location
Sleep Quality
Rooms
Service
Value
Cleanliness
Traveller rating
Excellent (322)
Very good (43)
Average (35)
Poor (26)
Terrible (37)
Depends on the room you are allocated !
May 14, 2025Karen 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
Great stay
May 11, 2025lindasG2340LJBad Vigaun, Austria
Great staff, lovely room, perfect location to explore Key West. We got great dinner recommendations. Fantastic bike rental cooperation with local company.
Pools a little small and breakfast choices could be better from our european point of view. But we would come back any time.
Paradise
May 9, 2025Colleen S
Very beautiful property. Staff friendly and helpful. Great breakfast and location. Plenty of things to do and see in Key West. Rooms were clean and housekeeping are outstanding. Atmosphere was wonderful and entertainment by the pool. Outstanding location.
Exactly what we needed.
May 7, 2025Elisa K
It was a last minute trip for our 20 year anniversary. The desk person was outstanding. She recommended some great places and was just a delight to talk with. Our room was perfect and the pool was really quiet and relaxing. We loved the breakfast and the bar. I plan on returning soon.
Return to Key West 30 years later, perfect return.
Apr 29, 2025Cecilia T
Highly recommend Winslow's Bungalows. Room was small but clean, bed very comfortable. Coffee every morning was fantastic. Bar and bartenders very satisfactory. Great location a few blocks from Duval. Very relaxing. An employee found and returned my wallet.
Depends on the room you are allocated !
