This gay-oriented 17-room B&B is the most stylish on the island and is perfect for those allergic to antiques. The rooms are spread over three buildings; most have king-size beds and are decorated with black armchairs and white linens, an effect that comes off as modern but not stark. The complex has a pool and a hot tub plus clothing-optional sunbathing on two private decks (the hotel is strictly 21-plus). Guests usually include as many lesbians as gay men, a rarity in Key West, which gives the place a more inclusive vibe: Mingling is mandatory at the poolside happy hour every afternoon. Try the made-to-order frozen piña coladas.

Originally built in 1920 by railway magnate Henry Flagler, Casa Marina reopened in December 2007 after a $43 million makeover and is now part of Hilton's Waldorf-Astoria Collection. The renovation was a stunning feat, restoring the place to its Golden Era glamour. (Sadly, the coffered wooden ceiling in the lobby is a reproduction: Ferocious termites chomped through the original.) The 311 rooms are now airy and loftlike, with dark woods, crisp white sheets, and ceramic tile floors. Rooms in the original building are the best, for their idiosyncratic layout and 15 rooms with large balconies. The nickel-and-diming on the small print (in addition to a $20 resort fee tacked on each day, Internet access costs $12) is irritating, but there are also unexpected free flourishes, like in-room Nespresso makers, hallway tables piled with copies of The New York Times, and pool attendants doling out gratis ice pops.

The Reach is Casa Marina's sister hotel, though it's on an entirely separate lot five minutes' walk away along the backstreets (1435 Simonton St.; 305-296-5000; www.reachresort.com). There's little difference between them in amenities or price: The Casa complex is a little more grand, though the 150 rooms at the Reach are more colorful, with bright accents like throw pillows in red and yellow. The clientele at both is Key West's most jet-set (expect to hear Italian, French, and German), though the pools at Casa Marina make it more popular with families.

Getting to this private island resort accessible only by boat or seaplane is "a unique experience in the Lower 48." Crushed seashell paths wind through Jamaican palms to individual bungalow suites with living rooms and outdoor showers. At a sunset dinner "we had perfect service, and visits from the tiny Key deer."

(30 rooms)

A small historic hotel with big resort amenities, the Marquesa is steps from raucous Duval Street. Four classic Conch-style houses with tin roofs, wraparound porches, and gingerbread railings surround a quiet palm- and bougainvillea-filled garden with two swimming pools. The 27 rooms and villa-like suites, some with covered porches, are filled with antique and reproduction Indonesian sleigh beds, armoires, and writing tables. The huge bathrooms are done in Italian green marble. It's the most polished inn in Key West, and probably the most luxurious. One of Key West's finest restaurants, Café Marquesa, is on the premises.

Internet entrepreneur Runi Goyal snapped up this rather careworn guesthouse and gave it a sensitive makeover in 2006, replacing the grubby and kitschy Key West interior with top-notch Victoriana. She also gained a Green Hotel certification for her simple but effective setup (paper billing is only provided on request, everything is strictly recycled, bathroom products are in pump dispensers instead of wasteful mini-bottles). The 13 rooms are basic but bright with floral bedspreads and wooden furniture. Some, like the Jacaranda and Tamarind, share a private deck as well. Not surprisingly, the tech is state of the art (flat-screen TVs with built-in DVD players, free in-room Wi-Fi). Old Town Manor does not have a pool, but the shady garden is a pleasant place to take breakfast, which includes gooey guava bread and fresh-baked banana-nut bread—all organic, of course.

It's no wonder Oprah had her birthday bash at Sunset Key. The exclusive Westin resort is located on its own private island a ten-minute boat ride offshore—a nice retreat when the scene in Key West proper gets too hectic. The one-, two-, and three-bedroom tin-roofed cottages have full kitchens, living rooms decked out in lively Old Florida decor (white furniture with vibrant yellow and blue accents), and wraparound verandas with Adirondack chairs. Another major bonus: The island's private beach has sand shipped in from the Bahamas, instead of from the rocky shores of the Keys.

Back on the Key West mainland, Westin also took over the onetime Hilton on the waterfront, reflagging it as the Westin Key West Resort & Marina in 2006 (305-294-4000; www.starwoodhotels.com). It's a more conventional hotel than the Sunset Key cottages, with rooms and suites in a large, low-slung big building that hugs the waterfront. Though it doesn't have Sunset Key's air of exclusivity and celebrity, it can be a better option since you won't have to wait for the boat to and from the island, there's ample on-site parking, and the view from your balcony of the sun setting over the ocean is magically romantic. Well, as long as the cruise ships that dock nearby and block the view have departed on time.