Casa Marina Key West, A Waldorf Astoria Resort

Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a long dock extends out to the shallows for laps and snorkeling. Just off the beach, two large pools are set into green lawns and lush landscaping in front of the Spanish-style main building, which is on the National Register of Historic Places. The hotel’s wooden coffered ceilings, arched entryways, red-tile roofs, and other key architectural details recall the hotel’s glamorous heyday, while the clean, refreshed rooms are entirely modern, with sleek wood-framed beds, white linens and curtains, and ocean views. Children under 16 stay for free and babysitting is available for adults who want to take a break at the Spa al Mare, which has an open-air cabana right on the sand for al fresco massages and treatments.