Winslow's Bungalows

Key West, Florida Keys

Star rating

2 Queen Essential Room
Bungalow Bar
Essential Room with Patio
1 King Premium with Sofa Bed
1 King Premium with Sofa Bed
2 Queen Essential Room
Bungalow Bar
Essential Room with Patio
1 King Premium with Sofa Bed
1 King Premium with Sofa Bed

The hotel

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 7000 newspapers and magazines. Resort fee and inclusions are subject to change and availability. 

*Denotes local charge. 

Rating summary

  • Location Image of the Tripadvisor rating
  • Sleep Quality Image of the Tripadvisor rating
  • Rooms Image of the Tripadvisor rating
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Traveller rating

  • Excellent (320)
  • Very good (43)
  • Average (34)
  • Poor (26)
  • Terrible (37)
Image of the Tripadvisor rating Paradise

مايو 9, 2025 Colleen 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.
Image of the Tripadvisor rating Exactly what we needed.

مايو 7, 2025 Elisa 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.
Image of the Tripadvisor rating Return to Key West 30 years later, perfect return.

Apr 29, 2025 Cecilia 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.
Image of the Tripadvisor rating Our room looked nothing like the pictures on their website!

Apr 24, 2025 LMNR75 Chaska, Minnesota

We were shocked to be shown to room #53 after paying over $500 per night to stay at Winslow's. I would have been upset to pay $200 a night for such a tiny room, much less $500! Our room looked nothing like the beautiful pictures on their website. After moving our suitcase into the room we didn't even have enough room to easily move around the bed.… قراءة المزيد
We were shocked to be shown to room #53 after paying over $500 per night to stay at Winslow's. I would have been upset to pay $200 a night for such a tiny room, much less $500! Our room looked nothing like the beautiful pictures on their website. After moving our suitcase into the room we didn't even have enough room to easily move around the bed. The bathroom only had a sink and a toilet, so nowhere to put any toiletries. The room itself needed a lot of maintenance: there was peeling paint and rust in the bathroom, lots of messy cords and crooked outlets by the air conditioner. There was a big, awkward step up into the bathroom. Oddly, only two of the shower walls were tiled, so the full spray of the shower hits the plaster wall across from the shower head, disaster waiting to happen. You should not be renting room #53 to anybody! After we complained, we were moved to another room of the same room type for the remainder of our stay and the other room was at least double the size! Unfortunately, it was right on Truman Ave. and there is zero soundproofing against the traffic noise. We were woken up all night by sirens and trucks and then roosters at 5 AM. The beds were comfortable but what good is that when the noise keeps you awake anyway. We were happier with our stay after moving rooms until our final day when we sat down at the bar with our friends. I merely asked the bartender a question about one of the food items listed on the chalkboard and he snapped "I wouldn't know!" He then got busy with other customers and when he finally came back to us he snapped, "it's after 2pm now and my chef leaves at 2pm." We were ready to order well before 2 pm. Our entire group got up and left. I don't have an issue with the hours but with the manner in which this employee chose to inform us he wasn't going to serve us. I wasn't going to leave negative reviews on this stay but this extremely rude bartender changed my mind! Read less
Image of the Tripadvisor rating Luscious gardens and well cared for bungalows. Comfy and cozy surrounded by charming interior decor.

Apr 21, 2025 jafogg Minneapolis, Minnesota

Our bungalow was perfect! Winslow Bungalows are located in walking distance of excellent restaurants, night life and museums. Beautiful, well maintained gardens with 3 different pools to choose from. This was our first time and we look forward to returning!