Winslow's Bungalows

Key West, Florida Keys

Virgin 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 (290)
  • Very good (43)
  • Average (32)
  • Poor (25)
  • Terrible (34)
Image of the Tripadvisor rating 32nd Anniversary Celebration

Nov 20, 2024 FroMonster Carrollton, Georgia, United States

We really enjoyed our stay at Winslow's. The staff were all wonderful and always helpful. The continental breakfast is better than the majority of places we've stayed at. The grounds were amazing. The location is convenient to Duval Street and a variety of restaurants. We'll be returning to Winslow's for future stays in Key West.
Image of the Tripadvisor rating Nice but…..

Nov 14, 2024 jackye106 Bradenton, Florida

Beautiful place, updated and maintained. Wonderful breakfast each morning. Staff very friendly. Issues were our room although it was clean, it was incredibly small. Only place to sit was on the bed. Bathroom was 35” wide! Hot water in the sink but not the shower. Four hundred plus a night was was overpriced. Also multiple issues with… Read more
Beautiful place, updated and maintained. Wonderful breakfast each morning. Staff very friendly. Issues were our room although it was clean, it was incredibly small. Only place to sit was on the bed. Bathroom was 35” wide! Hot water in the sink but not the shower. Four hundred plus a night was was overpriced. Also multiple issues with credit card upon leaving. Read less
Image of the Tripadvisor rating Key West vacation

Nov 12, 2024 tim p Metairie, Louisiana

The accommodations, services and location was great. We really enjoyed our time in Key West. The desk and breakfast staff were outstanding. The bed and bedroom was very comfortable. We were able to walk to all of the restaurants and bars that we enjoyed.
Image of the Tripadvisor rating Must Stay Here!

Nov 11, 2024 HistoryGoneFifing

This inn is amazing! It has such comfy beds that the only thing that gets you up in the morning is the thought of eating that delicious breakfast. They have fresh pastries, fruit, all manner of breakfast items but the best surprise was the cheese grits - as good as my mama made. But far and away the best part of the stay was the friendly, helpful… Read more
This inn is amazing! It has such comfy beds that the only thing that gets you up in the morning is the thought of eating that delicious breakfast. They have fresh pastries, fruit, all manner of breakfast items but the best surprise was the cheese grits - as good as my mama made. But far and away the best part of the stay was the friendly, helpful staff. Special recognition must go to Teqila and Ursula at the front desk. Oh, my goodness, they were amazing. If you’re in Key West, I highly recommend this inn! Read less
Image of the Tripadvisor rating Thank you Teqila and Ursula at Winslow’s Bungalows!!!

Nov 11, 2024 HEATHER J

The staff and accommodations at Winslow’s Bungalows were top notch! Special shout out to Teqila and Ursula for helping us with everything we needed to make our stay even more enjoyable. They were so friendly and helpful I would highly recommend this place to anyone traveling to Key West ❤️