Winslow's Bungalows

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Key West, Florida Keys

4 stars

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

Explore the local area

Located in Key West, Florida, 800 yards from Duval Street and 0.6 miles from the Southernmost Point.

Hotel Information

Room Information
Room Upgrade 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.

Hotel details

Resort Fees

There is an amenity fee of $45 plus tax per room per night (payable locally, fee subject to change).

Resort Fee Details

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.

Dining

Complimentary continental breakfast served daily. Bungalow Bar (outdoor pool bar with daily happy hour). Dogs and People food cart (serving light fare).

Fun and Games

3 outdoor swimming pools. Bicycle rental*. Discounted spa services available at Prana Spa*.

Handy Stuff

Complimentary WiFi access. Concierge. Self-parking $20 plus tax per day (payable locally, fee subject to change).

Additional Information

*Denotes local charge.Minimum Check in age 21 Years.

Trip advisor rating

4.3/5

520 reviews

Location
Sleep Quality
Rooms
Service
Value
Cleanliness

Excellent

69%

Very Good

Average

Poor

Terrible

“Spectacular”

Aug 01, 2026Jorge L

Quiet, beautiful, serene property. Great atmosphere and service. Highly recommend it, especially for couples.

“The best of Key West”

Jul 29, 2026Bill C

I went with 3 friends and it was the best stay we have ever had in Key West. The staff, resort and rooms were excellent. We will be back.

“Most Expensive Motel I’ve ever stayed in”

Jul 26, 2026Road15113859005

We only stayed here because it was a last-minute trip and this was the only place available. We wish we had stayed at the Best Western instead. The positives: the location is great, the front desk employee was friendly and genuinely tried to help with our complaints, and the three pools were nice and usually empty. However, we watched guests let their dog into the pool despite posted signs prohibiting it. Now for the reason this place deserves its rating. At nearly $1,500 for a weekend, calling this a "luxury stay" is laughable. If your idea of a resort breakfast is stale pastries, black coffee, and packets of instant oatmeal, you'll be thrilled. If you want something as basic as eggs, that'll be another $7. Housekeeping was even worse. For what they charge, you'd think they could manage to wipe down a sink. Instead, one of our robes disappeared after the first night and was never replaced. We called multiple times for towels and, after waiting over five hours, gave up and used pool towels. Room "cleaning" didn't happen until around 5:00 p.m., which completely defeats the purpose of having your room serviced during the day. Oh and don’t expect to have wifi during your stay, as our room appeared to be a “dead zone”. This property charges luxury resort prices while delivering motel-level service. You're paying for a name and getting almost nothing in return. Save your money and stay literally anywhere else.

ATOL protection for your entire holiday

Book with confidence knowing your holiday is financially protected

Protection for your Package Holiday

Some of the flights and flight-inclusive holidays on this website are financially protected by the ATOL scheme. However, ATOL protection does not apply to all holiday and travel services listed on this website. Please ask us to confirm what protection may apply to your booking. If you do not receive an ATOL Certificate then the booking will not be ATOL protected. If you do receive an ATOL Certificate but all the parts of your trip are not listed on it, those parts will not be ATOL protected. Please see our booking conditions for information, or for more information about financial protection and the ATOL Certificate go to: https://www.atol.org/about-atol/atol-certificates.

This product offers you combinations of a hotel and flights at an inclusive price. This product enjoys the protection of the Package Travel, Package Travel and Linked Arrangements Regulations 2018.

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