Casa Marina, A Waldorf Astoria Resort has all the pedigree you'd expect from a hotel featuring the legendary Waldorf moniker. The ornate seaside haven has lived through prohibition, a war, and that pesky missile crisis. Today it stands proud and gleaming following a tip-to-tail, $43-million restoration. From the manicured palms and gardens, to every corner of the hotel and the 1,100 square feet of pristine Key West beachfront, the resort is flawless and refreshing at every turn.

Deep wooden hues, white walls, and lovely white sheets accent the 311 rooms' already breezy ambiance. Once you unpack, unwind at the spa. Just follow the smell of aromatherapy, and the oohing and aahing emanating from the massage rooms.

Take it easy at the pool, or go big in the ocean with all sorts of water sports, fishing, diving, and snorkeling. After you've seen all there is to see in the surf, switch to turf at the Strip House at Reach Resort. Deep red walls will transport diners to Gotham over prime cuts, and signature items like Shell Fish Plateau, Goose Fat Potatoes, and Maine Lobster Linguine. Unlike NYC though, you won't need to go through the trouble of hailing a cab after.