Winslow's Bungalows - Key West Historic Inns

We never felt crowded or surrounded by tourists, even with around 80 rooms on the property. The location was ideal, just a couple of blocks from Duval, and we walked everywhere. The grounds were gorgeous and lush, the front desk team was the most outgoing and helpful I’ve encountered at a hotel, and breakfast was a beautiful spread. Don’t miss the sugared waffles! The bartender also makes an amazing pina colada. I liked it enough to have one every day. My husband, two friends, and I booked a long weekend at Winslow's Bungalows and had an amazing stay. Stay here!

We loved bungalow 57 when we stayed in January 2025. It was quiet at night, just far enough off Duval, but close enough to walk everywhere. The room had plenty of space and a comfortable bed. We spent our evenings on the big front porch and had coffee up on the rooftop deck. The breakfast area was cute, with meats, cheeses, hard-boiled eggs, fruit, breads, bagels, pastries, coffee, tea, and juice. I stayed with my boyfriend, and we’ll be back. I highly recommend this place to everyone!

We could walk from Winslow’s Bungalows in Old Town to all the sights and restaurants on our list. The grounds were beautiful and peaceful, and our room was spacious and comfortable. Everyone we met on staff was pleasant and helpful. Sonya deserves special thanks for going above and beyond to fix a glitch with our reservation. This was our first visit to Key West, and choosing Winslow’s Bungalows worked out great. We highly recommend staying here.

Having a bar by the pool was a real plus, and there were three pools to choose from. The rooms weren’t all alike: some were bungalows, some stood on their own, and others felt more like part of a hotel. We had easy access to Duvall while staying away from the cruise ship crowds. The staff were excellent at taking care of small details, like putting a happy anniversary sign above the bed before we came in. Breakfast was continental style, but good, with plenty of coffee.