Embracing Key West's only natural beach, this full-service, luxury resort offers sleek rooms with modern amenities as well as shared access to its sister Casa Marina resort nearby. Its roots go back to the 1980s, when locals rallied against the loss of the topless beach it displaced; as a tip of the hat to the city's bohemian spirit, the resort devotes a portion to topless sunbathing. And then there's the Strip House, its naughty little steak house with nude images and
a bordello feel. High-end touches include turndown service and plushly lined seersucker robes in the room as well as life-sized chess and boccie in the courtyard and a pool concierge delivering popsicles and drinks du jour. Guests are privy to the spa, tennis, and other amenities at Casa Marina. Rooms with various layouts contain all the conveniences, including iPod docks, espresso machines, and wet bars. The private pier-gazebo makes a perfect spot for weddings and watching the sun rise.