Clevelander Hotel

Off Ocean Drive's Art Deco strip, the Clevelander occupies a 1930s building whose streamline-moderne facade fronts a poolside bar that doubles as Miami Beach's longest-running open-air music venue. Four stories wrap the courtyard pool, where a DJ booth runs afternoons into evening.

Rooms skew compact, built for guests who plan to spend daylight hours poolside rather than in-room. South Beach's sand sits directly across Ocean Drive, while Lincoln Road's shops are an eight-minute walk north — a fit for travelers prioritizing nightlife access over quiet.