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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 417 reviews
Rating summary
Location
Sleep Quality
Rooms
Service
Value
Cleanliness
Traveller rating
Excellent (285)
Very good (42)
Average (31)
Poor (25)
Terrible (34)
Great find!
Oct 28, 2024Climber41640355295
Beautiful grounds tucked away from the chaos of Fantasy Fest, but close enough to comfortably walk to Duval St. Rooms were nice. Paid for parking on site which was not noted in our reservation. Continental breakfast was fabulous, not your commercial hotel spread. Pools and little sitting areas with hammocks and swinging chairs were awesome.
Would stay here again
Oct 12, 2024AM MToms River, New Jersey
The grounds are beautiful and well maintained. The bar area is comfortable and there are plenty of drinks to choose from and it even has a small menu with plenty variety. The continental breakfast is way more than continental. They truly go the extra mile for this.
The rooms are clean. However, housekeeping only came if we requested it. I…
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The grounds are beautiful and well maintained. The bar area is comfortable and there are plenty of drinks to choose from and it even has a small menu with plenty variety. The continental breakfast is way more than continental. They truly go the extra mile for this.
The rooms are clean. However, housekeeping only came if we requested it. I asked at the front desk if we were supposed to ask for housekeeping and they said no they are supposed to come daily.
We stayed in room 65 and were a little disappointed to not have a balcony. The bathroom was very tight. The shower reminded me of our tiny shower in our RV and the sink was so small every time I washed my face there was water all over the floor. There is a safe and small refrigerator in the room. The a/c worked great!
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Historic Key West
Oct 9, 2024Bob P
We were looking for a classic Key West Inn in a great location. We found it here! My wife thought it was our own tropical paradise. Loved the food, staff and the room. Our favorite meal was at the Cuban Coffee bodega two blocks from the hotel toward Duval Street
Highly Recommend
Sep 24, 2024scott2003Houston, Texas
This is our third time at Winslow and it did not disappoint. We were a little worried when it was no longer a Kimpton but you could barely notice the difference. Staff was wonderful and the patio room we had was perfect. Having lived in KW for a number of years we choose this property when we go back. Highly recommend.
Not good
Sep 21, 2024Jennifer J
The property is great, and normally the customer service is excellent, however, the customer service we experienced on our current visit makes me question whether we will stay here again. We were treated rudely at the front desk when we inquired about pool towels. Neck rolling and hand gestures were not necessary. Very sad for such a good…
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The property is great, and normally the customer service is excellent, however, the customer service we experienced on our current visit makes me question whether we will stay here again. We were treated rudely at the front desk when we inquired about pool towels. Neck rolling and hand gestures were not necessary. Very sad for such a good location. Oh well, mgmt doesn't seem too concerned with the situation so I guess I shouldn't be either.
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Great find!
Would stay here again
Not good
