Moorings Village The yin to Cheeca's yang, the Moorings is passive, discreet, subdued—and right next door. There's no bellhop to lead you to your Bahamian-style cottage or to point out the Balinese furniture and artifacts, large soaking tubs, and well-appointed kitchens. No housekeepers come (unless you ask). There's no room service. You're left utterly alone to enjoy this converted coconut plantation, the hammocks and beach chairs expertly positioned on sand brought in from the Caribbean. Proprietor Hubert Baudoin, a windsurfing Frenchman, sometimes rents the place out for photo shoots, which is why you might see models reclining on the trunks of wind-bent palms. But most of the time you'll see no one at all. 123 Beach Rd. (MM 81.6 Oceanside), Islamorada; 305/664-4708; www.themooringsvillage.com; doubles from $200 (two-night minimum), cottages from $3,325 a week.
MIDDLE KEYS Hawk's Cay Resort This 60-acre playground is geared largely toward families, sportsmen, and conventioneers. Besides the 177 guest rooms, there are 269 villa units and an 85-slip marina. Yes, it's gargantuan, and it can feel crowded, but the resort provides plenty of opportunities to filter out the noise and focus your mind—whether on a tennis ball, the massage you're getting at the brand-new spa, or the tug at the end of your fishing line. Hawk's Cay is renowned for its kids' activities: a water slide in the shape of a pirate ship, movies by the pool, miniature golf, even teen facials. 61 Hawk's Cay Blvd. (MM 61 Oceanside), Duck Key; 800/432-2242 or 305/743-7000; www.hawkscay.com; doubles from $250, villas from $425.
LOWER KEYS Little Palm Island The theme of this resort could be Gilligan's Island set in the Raj. There are 30 duplex units on a mere six acres, so privacy, while respected, is secondary to a sense of isolation. After all, only a select few are willing to spend upwards of $895 a night in the Keys, meals excluded. What do you get for all that?Enthusiastic and diligent service. A roomy suite under a thatched roof, with ocean viewsand bamboo-enclosed outdoor showers. And thoughtful touches like your name in wood blocks above the door. 28500 Overseas Hwy. (MM 29 Oceanside), Little Torch Key; 800/343-8567 or 305/872-2524; www.littlepalmisland.com; doubles from $895.
KEY WEST HOTELS
The question of where to stay in Key West mirrors, in a way, the town's own existential dilemma. Guesthouses represent the past—eccentric, architecturally distinctive. Resorts signify Key West's evolution into a mainstream destination. At one extreme are inns campy enough to make Liberace look like Charlton Heston; at the other, properties much like those anywhere else in America. Between the two poles, however, are places of character and comfort, listed here.
Artist House This fabulous purple Victorian mansion has seven rooms and adornment to spare. Traditional Southern elements predominate: wingback chairs, four-poster beds, acres of swag—enough to make you want to put on a hoopskirt and a bustle. 534 Eaton St.; 800/582-7882 or 305/296-3977; www.artisthousekeywest.com; doubles from $139.
Gardens Hotel Peggy Mills bought this 1870's house in 1930 and set about creating a showpiece botanical garden. She brought in 87,000 paving bricks, a Moorish fountain, and four tinajones, huge earthenware jars from Cuba that each weigh a ton. After her death, the place became a hotel with 17 rooms spread among five buildings. Breakfast—croissants, Key lime beignets—is served in the solarium. But you'll spend more time lolling in the pool, smelling the jasmine, and drinking a toast to Miss Peggy. 526 Angela St.; 800/526-2664 or 305/294-2661; www.gardenshotel.com; doubles from $265.