14 Best Hotels in the Florida Keys, From Private Islands to Beachy Bungalows

"A campus of multiple, white-washed cottages and former homes cast predominantly in classic Key West architectural style, Winslow’s Bungalows is a history-steeped retreat two blocks from Duval Street. Formerly part of the Kimpton portfolio, the 85-unit property still oozes retro-chic decor and draws a cool (often pet-obsessed) crowd. Not much has changed since reintegrating into Key West Historic Inns Collection in January 2024: Winslow’s retains an intimate setting, where you’ll feel more like a guest in a private home than in a hotel. Several pools, including a large heated one, and lots of relaxation nooks (hello: hammocks) dot the beautifully landscaped enclave, and continental breakfast is a standard inclusion in all stays. Though Winslow’s remains pet-friendly in life after Kimpton, there is a nightly fee worth noting ($50 per pet, per night). Considering the campus houses one of Key West’s oldest homes and oldest lodging, dating to 1856, it’s worth asking the front desk for a quick primer in Winslow’s history." - Paul Rubio, Nancy DePalma