Overall Ratings & Reviews Winslow's Bungalows - Key West Historic Inns

Historic area and beautiful lush garden landscape around all the houses.

Easy check-in process. The room was great with a beyond comfy bed.

I’ve been to Key West several times and I have to say I’m very disappointed with the hotel in general. Our room was not featured in any photos on the website, and I dont feel there was an accurate depiction of the rooms at all. The room was dirty upon arrival and the headboard was especially disgusting. The room was a closet, and barely enough room to walk around the bed. Every day, for 3 days in a row I had to ask for pool towels as nothing was stocked by the pool. I feel for what I paid it did not reflect my expectations. The staff was friendly unfortunately that was the hotels only real redeeming quality.

Amazing place with excellent service and very friendly people. Would recommend it to everyone and definitely be back.

Breakfast was fresh with many options. Staff are friendly. Quiet property but walkable to nightlife, shopping and dining. We loved that our room had a private balcony and sitting area to relax outside our room. The large walk in closet and spacious bathroom was nice. Be sure if you can’t do stairs to make a note when reserving because many rooms are up narrow staircases.

Great area and great place to stay!

The pool was out of order for 2 days of stay. There are 2 on the property. We stayed for 5 days and the sheets were not changed. The room did not smell fresh upon entering. I know things are humid and this can contribute to mustiness. We enjoyed the experience overall. The breakfast each morning was very nice.

Everything was beautiful and amazing about Winslow Bungalow! It felt like being at a resort! The grounds were gorgeous! The Staff were friendly and accommodating! The food and drinks were delish! The room was clean and comfortable! We will be back!

The property was quaint, private and well kept with lush, tropical foliage. The staff was friendly and welcoming. They were very accommodating allowing us early check-in with our arrival on the ferry. The "welcome drinks" at the bar was a nice touch that was thoroughly enjoyed. Breakfast was wonderful with alot of choices and many healthy options. Rooms were comfortable. Location close and convenient, within walking distance, of many attractions, restaurants and shops. Loved our stay and there will definitely be a return trip

Loved it!

Property is turn of the century Florida, which we loved. Flooring had some weak spots in the bedroom. The room was updated. Loved the sitting areas outside the rooms and variety of swimming pool options on site.

Amazing accommodations. Loved the cute little bungalow we were in with a front porch. Staff was friendly and responsive.

Service was good but room #79 near the pool isn't well located.

Beautiful oasis in the heart of Old Town Key West. The staff was friendly and helpful, from the front desk at check in to the bartenders, to the pool and custodial staff. The three pools form hubs from which the rooms and amenities branch off. Staying in the Annex was a smart choice as we could retreat there and be just off a pool or wander not too far back to one of the two main pools by the bar and lobby. My only critique is that the bed and pillows were too soft for my liking and they didn't advertise options to swap them out. Being a bit creaky on vacation (even without all the walking through town) isn't that pleasant. Thankfully a float in the pool and ocean helps. But the AC going on and off through the night was also frustrating. It was very loud for a fairly luxury place. Replacing it with something quieter would go a long long way. Otherwise, I'd come back next time we head to the Keys!

Staff was great & property was beautiful.

The property was in excellent shape, the amenities were lovely and the staff was friendly.

Winslows gives the perfect Key West Vibe and is right on US1 (Truman) minutes away from pretty much everything in Old Town. My only issue is that bartender, Keith has an attitude as if he would rather be anywhere but there, unless he has a full bar, then he can turn on the proverbial charm. The rest of the staff is superb.

This hotel was lovely! We stayed in the treehouse room. I would definitely visit again!

We went to Key West on a whim and I’m so happy we found this beautiful, intimate property. Beautifully decorated, very comfortable and near to everything. The front desk staff were incredibly friendly, and we used all of their recommendations. We had only planned one night in Key West before heading farther up the Keys, and we will come back again to stay at the Winslow. It was exactly what we needed for a spontaneous weekend away!

Our stay here was magical! We arrived around midnight due to flight issues and were met by a friendly Manager to check us in. The grounds are gorgeous and there's little areas all over the property to tuck yourself away and read a book or enjoy a drink. We stayed in the Annex across the street. It was so cute and we had our own little pool all to ourselves the entire time. It's a very quick walk to the "main" pool by the bar and restaurant. The complimentary buffet for breakfast was wonderful and the drinks at the bar were delicious! I really appreciated the purified water stations for refilling our bottles. The location of the Winslow is hard to beat. Your right smack dab in the middle and can be anywhere on the island in 5 minutes to 15 minutes via bike. Definitely rent a bike, it's so much fun to cruise around!