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 469 reviews
Rating summary
Location
Sleep Quality
Rooms
Service
Value
Cleanliness
Traveller rating
Excellent (327)
Very good (44)
Average (35)
Poor (26)
Terrible (37)
Perfection
Jul 28, 2025cliffm928
This has to be our favourite hotel of all!
First the staff is phenomenal.
Jennifer is absolutely wonderful and so accomodating.
Sonya made our stay exquisite and couldn’t do enough to make it better.
Kya is a sweetheart from the reception on checking in to helping each day.
Keith at the bar and the entire housekeeping staff was fabulous and I…
Read more
This has to be our favourite hotel of all!
First the staff is phenomenal.
Jennifer is absolutely wonderful and so accomodating.
Sonya made our stay exquisite and couldn’t do enough to make it better.
Kya is a sweetheart from the reception on checking in to helping each day.
Keith at the bar and the entire housekeeping staff was fabulous and I can’t say enough about breakfast and the wonderful staff preparing and servicing you needs.
The property is a well oiled machine from the employees to maintenance.
It truly feels as though you’re in the Tropics.
Resorts should take a lesson on how they should treat guests on vacation.
A 5 doesn’t do it justice
Thank you
Read less
Our new favorite spot
Jul 25, 2025kristinadA9715DX
It’s such a cozy and peaceful and beautiful place. Love the atmosphere and the breakfast was amazing and all the people that work here are so nice. We will be back here again!!! Our new favorite place!! Pool is amazing too and also music is great!!
10/10 would come back here!
Jul 18, 2025daricegallBranford, 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.
Well needed Vacation and it was.... Amazing
Jul 10, 2025Claudia 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.
Cute but not Quiet
Jul 6, 2025Lindsey JFranklin, 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.
Perfection
