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

"Tucked away on Stock Island, a land bridge away from Key West, is the surprisingly modern, naval-inspired Perry Hotel, named for military figure Commodore Perry, who in 1822, planted the US flag in Key West and claimed the Florida Keys as United States territory. The open-plan lobby and 100 guest rooms feature nautical art from Stock Island artists, beginning with a full story of upcycled propellers framing the check-in area and maritime artifacts draped from the entrance ceilings. Rooms are artsy, bright, and beachy, with spacious balconies yielding marina, resort, or sunset views. On-site, there are 300 boat slips, two swimming pools, dockside benches, multiple fire pits, and three solid restaurants, the newest of which is the dockside Mexican restaurant, Bad Boy Taqueria and Tequila, opened in late 2023. This property tends to attract those keen on exploring the Keys’ vast water world—immediate, on-site access to top outfitters in fishing, snorkeling, sailing, and diving is a key consideration. It also appeals to those who want to be a quick, free shuttle away from the fun of Key West, but appreciate the resort’s 10 p.m. noise curfew. Finally, despite a hefty $75/night fee, it’s a favorite among dog lovers thanks to two on-site dog parks and prolific pet-friendly dining and lounging spaces." - Paul Rubio, Nancy DePalma