What to expect: Since 1946, the Cheeca Lodge & Spa has attracted sportfishing enthusiasts such as sportscaster Curt Gowdy, General Norman Schwarzkopf, and President George H.W. Bush, as well as families seeking active vacations. "Barefoot elegance" is the theme, and it's evident in the lobby with a wood-beamed ceiling, wood-paddle ceiling fans, plush seating, and lots of plants.

Amenity highlights: Waves lap a palm-lined, 1,100-foot beach furnished with tiki torches and thatched cabanas. A classic wood pier jutting 525 feet into the Atlantic Ocean is ideal both for fishing and moonlight strolls. Guests swim in a saltwater lagoon, a large family pool, or a 25-yard adult lap pool. The resort also has a nine-hole golf course and six lighted tennis courts. Water-sports rentals, sunset cruises, and fishing trips are available (surcharges).

What to expect: With 65 rooms on 6.5 acres, Chesapeake Resort is an expansive, casual resort appealing to vacationers looking for space, sunlight, water, and tranquility. Quieter than other family destinations in the Keys, the resort still provides ready access to water sports and charter-fishing boats. Lounge chairs, a few palm trees, hammocks, and thatched sun shelters add to the deserted-isle ambience.

Insider tip: Above the harbor's fishing-charter shack, a weathered-wood platform shaded by a thatched roof contains rocking and lounge chairs for enjoying panoramic Atlantic Ocean views.