Casa Marina Resort

Since opening its doors on New Year's Eve in 1920, the Waldorf Astoria-owned Casa Marina has served as a beachfront hideaway for Hollywood's elite (Rita Hayworth and Gregory Peck have both rested their heads here) and everyday travelers. Situated on a private beach (Key West's biggest), the landmark hotel underwent a major $43 million renovation back in 2007, which brought state-of-the-art amenities and a breezy, tropical style to the Art Deco grande dame's 311 rooms and suites—all of it just a short walk to bustling Duval Street.