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 7,000 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
  • Service Image of the Tripadvisor rating
  • Value Image of the Tripadvisor rating
  • Cleanliness Image of the Tripadvisor rating

Traveller rating

  • Excellent (329)
  • Very good (44)
  • Average (35)
  • Poor (26)
  • Terrible (37)
Image of the Tripadvisor rating Enjoyed our stay here...

Sep 2, 2025 Navigator28176010568 Rochester, New York

The place is awesome. The rooms are cozy and comfy. The pool is relaxing. Nice small bar area with some decent food choices. The area outside is well kept and looks amazing.
Image of the Tripadvisor rating Fantastic clean hotel!

Aug 21, 2025 839travism Cincinnati, Ohio

Beautiful hotel! Very tropical atmosphere. Breakfast was fantastic every morning! We had Belgian waffles, fresh fruit cups, pastries, cheesy grits which were to die for! Chia pudding, wellness shots, and fresh OJ. Days we would sit at the pool there was live music one day, popsicles handed out, and a day of samples of rum. Staff was always… Read more
Beautiful hotel! Very tropical atmosphere. Breakfast was fantastic every morning! We had Belgian waffles, fresh fruit cups, pastries, cheesy grits which were to die for! Chia pudding, wellness shots, and fresh OJ. Days we would sit at the pool there was live music one day, popsicles handed out, and a day of samples of rum. Staff was always working hard. We did have an almost empty shower gel and I had to ask 3 times to get some more. They said they were out of it but ended up bringing us some. It is a good walk to Mallory Square but not far from Duvall Street and the Southernmost Point. Other than that it was fantastic! Such a great little getaway! We would stay there again. Read less
Image of the Tripadvisor rating Perfection

Jul 28, 2025 cliffm928

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
Image of the Tripadvisor rating Our new favorite spot

Jul 25, 2025 kristinadA9715DX

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!!
Image of the Tripadvisor rating 10/10 would come back here!

Jul 18, 2025 daricegall Branford, 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.