Winslow's Bungalows - Key West Historic Inns in Key West

We loved staying here and will definitely be back. Great location near to Duval Street. There are lots of beautiful white individual rooms like little houses in this complex, we had ones across the street from the main place and loved it. They have a nice bar and a good breakfast in the morning time. Such a cute place with nice staff. Only thing I'd say would be to have a set of drawers in our room or wardrobe as we only had a few hangers on the wall for our stuff.

Booked Winslow's Bungalows for a long weekend with my husband and two of our friends. Our stay was absolutely amazing! The front desk staff were the most outgoing and helpful I have ever encountered at any hotel, absolutely gorgeous lush grounds, and a beautiful breakfast spread (don't sleep on the sugared waffles!) There are 80 or so rooms on the property so it never felt overly crowded or touristy. The bartender makes an amazing pina colada, so great in fact I had to have one each day 😉 Lastly, the location is perfect... Just a couple of blocks from Duval and we walked everywhere. Stay here!!

I stayed with my boyfriend in bungalow 57 in January 2025 and we loved it! The location was close enough to walk everywhere but far enough off Duval to be quiet at night.
The breakfast area was cute and offered meats, cheeses, hard boiled eggs, fruits, breads, bagels, pastries, coffee, tea and juice. What we loved most was the relaxing areas. We sat on our large front porch every night and had coffee on the rooftop deck. Bed was comfortable and room we had plenty of space. We will be coming back and I highly recommend this place to everyone!

Beautiful property and great location. This was our third time in Key West and our first time to stay at Winslows Bungalows. We normally stay near the harbor but wanted to try a different spot that was more quaint away from the crowds. While the property was beautiful, the rooms are very small. When we booked, the only available room was the Winslet. The room
Was really tiny and seemed a little dated. My husband and I had considered checking out after the first night and changing hotels but when I went to the front desk to express my concern they were very helpful in moving us to a much bigger room, that was more spacious. That room was much more comfortable. Each night I did have to request extra towels since they only provide you with two and they never once hesitated to bring extras. I wouldn’t mind staying at the property again for the simple fact of how accommodating the staff was. It wasn’t their fault I waited until the last minute to book a room and ended up with one so tiny but their willingness to upgrade would be the reason I would stay again. It wasn’t terrible and didn’t make me enjoy Key West any less. So if you are looking for a beautiful, quaint place to stay, this is your spot. You don’t even need to set an alarm clock either - the roosters will make sure you are awake! To me that was true Key West charm.

The front desk guys were awesome. Rooms were very nice and beds very comfortable. Bathrooms a bit small but showers were great. Everything was clean and if u need anything they will get it for you asap. Control of fan and AC was very easy to adjust. Really enjoyed our stay

Room and bathroom were sparkling clean, and the hotel is well-located in Key West for all main attractions. There was live music when we arrived on Saturday afternoon, which was a pleasant surprise, and we were able to check in early (2pm). The continental breakfast is a nice inclusion, but unfortunately they had run out of almost everything (including coffee) by 9:30am. The front desk was also quite difficult to contact after 7pm. We tried both in-person and over the phone but were unable to reach anyone until 10am the next day. Overall a pleasant stay and we would come again.

The property is very lush and serene. It feels secluded but is within walking distance to Duval Street and many other local attractions. There is a bar right next to one of the swimming pools with great food and drink options. Our room was spacious and very clean. Only giving 4 stars because the continental breakfast could have been a bit more robust.