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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 409 reviews
Rating summary
Location
Sleep Quality
Rooms
Service
Value
Cleanliness
Traveller rating
Excellent (279)
Very good (41)
Average (31)
Poor (24)
Terrible (34)
Charming Bungalow Resort!
Sep 7, 2024Carly I
Winslow’s feels like an oasis in the middle of Key West. The foliage throughout the property is lush and well kept, and is a great escape from the hustle and bustle of downtown Key West while still being walking distance to all the main sights! Breakfast was PHENOMENAL and the best I can remember having at a hotel- daily fresh smoothies, overnight…
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Winslow’s feels like an oasis in the middle of Key West. The foliage throughout the property is lush and well kept, and is a great escape from the hustle and bustle of downtown Key West while still being walking distance to all the main sights! Breakfast was PHENOMENAL and the best I can remember having at a hotel- daily fresh smoothies, overnight oats, cheesy grits, yummy coffee! I had a virgin pina colada for my welcome drink and it was so good, not too sugary with what tasted like fresh coconut. Only complaint was that our room was pretty noisy (39) and we were woken up by the footsteps of the folks in the room above us every morning. However, we booked the standard room class, so booking one of the standalone bungalows would remedy this. As other reviews mention, the AC was loud, but it was a constant drone so we slept through it easily. All in all, Winslow’s was delightful and I would highly recommend it!
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Key West Best
Sep 3, 2024cliffm928
We have stayed here numerous times over the years when it was an IHG property.
Well let me tell you that the best thing that has happened is that they’re independent now.
The entire the staff Joy(Director) Jennifer,Sonya, Lemi, Mike, Danny, Keith, Tequila and Kya were the best we have experienced in our travels, Friendly, warm, hospitable and…
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We have stayed here numerous times over the years when it was an IHG property.
Well let me tell you that the best thing that has happened is that they’re independent now.
The entire the staff Joy(Director) Jennifer,Sonya, Lemi, Mike, Danny, Keith, Tequila and Kya were the best we have experienced in our travels, Friendly, warm, hospitable and could not do enough enough for you to make your stay enjoyable.
The hotel is tropical and cozy just simply beautiful!!
Major Hotels take a lesson on how it should be done!!!
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Incredible hotel
Aug 25, 2024kate mlondon
Amazing hotel very stylish has an La feel too it
lovely staff and such a cool vibe so reasonable for what you get breakfasts are sensational five star
Beds so comfy and full of charm
They even hand out free ice creams thought of everything for a lovely stay
Lush landscape and great amenities
Aug 12, 2024Brandy C
A beautiful property with great amenities. We really enjoyed the lush landscape and crisp white, historic buildings. The staff was great and the breakfast and coffee bar every morning were such an added bonus. It had all of the bonuses of a big resort without the crowds. It had 3 pools to choose from with plenty of seating and towel service. We…
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A beautiful property with great amenities. We really enjoyed the lush landscape and crisp white, historic buildings. The staff was great and the breakfast and coffee bar every morning were such an added bonus. It had all of the bonuses of a big resort without the crowds. It had 3 pools to choose from with plenty of seating and towel service. We loved the welcome cocktail and the afternoon popsicles. The bar staff was very friendly and welcoming. We will be back!
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Amazing place
Aug 7, 2024Melanie J
Winslow’s Bungalows is a good place to stay. Staff are really nice. Good location, close to everything.
Charming Bungalow Resort!