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La Concha Key West, Autograph Collection

Key West’s tallest building (a whopping seven stories) and one of its original hotel classics from way back (1926), this pale yellow-stucco landmark astride upper Duval Street has long depended on the kindness of both a loyal clientele and history made by the likes of Ernest Hemingway (who wrote it into To Have and Have Not) and Tennessee Williams (who penned A Streetcar Named Desire here). La Concha has managed to keep up with the times fairly nicely while preserving key elements of its historic flair. Room decor is updated retro with louvered shutters. The onsite restaurant is called Perla. But in a location like this, of course, all of Duval Street dining—both highbrow and low—is at your feet. If you want to sleep better at night, ask for a room in back.