Key West’s tallest building (a whopping 6 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). Now part of the Crowne Plaza brand, the La Concha has managed to keep up with the times fairly nicely while both preserving key elements of its historic flair. Room decor is updated retro with louvered shutters; there’s a new rooftop spa whose treatment rooms have the best view in town; and a good restaurant called Jack’s Seafood Shack (Florida snapper meunière a top catch), 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.