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Key West Hotels

$200-$299
Editor's Pick
Hotel Photo
Alexander's Guesthouse
1118 Fleming Street
Key West , Florida
33040
Tel: 800 654 9919 (toll-free)
Tel: 305 294 9919
info@alexanderskeywest.com
www.alexanderskeywest.com

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.

$199 or less
Editor's Pick
Angelina Guesthouse
302 Angela Street
Key West , Florida
33040
Tel: 888 303 4480 (toll-free)
Tel: 305 294 4480
theangelina@aol.com
www.angelinaguesthouse.com

As Key West slowly goes upscale, it becomes increasingly challenging to find reasonably priced accommodations. Thank goodness for Angelina Guesthouse. Located in Bahama Village, the property has 13 rooms done in pastel greens, yellows, and blues, which give it a cool, Caribbean feel. The four least expensive rooms share a bath, though the rest have private facilities. Rooms 8 and 9 are a bargain for families, since each has two full-size beds and will sleep four, albeit cozily (note that room 12 is the only one with a TV, but there is free Wi-Fi property-wide). The smallish pool is the place to congregate each morning as the owners dole out hot homemade cinnamon rolls. Not surprisingly, this place fills up quickly, even off-season in July or August, so book ahead.

$300-$399
Editor's Pick
Hotel Photo
Casa Marina Resort & Beach Club
1500 Reynolds Street
Key West , Florida
33040
Tel: 866 397 6342 (toll-free)
Tel: 305 296 3535
Fax: 305 296 4633
www.casamarinaresort.com

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.

$300-$399
Editor's Pick
The Gardens Hotel
526 Angela Street
Key West , Florida
33040
Tel: 800 526 2664 (toll-free)
Tel: 305 294 2661
reservations@gardenshotel.com
www.gardenshotel.com

The former estate of Peggy Mills, a local garden lover, is now a romantic retreat situated in a lush botanical setting intertwined with walkways and dotted with fountains. The 17 rooms are dispersed among the Peggy Mills Mansion (listed on the National Register), two additional Bahamian-style structures built in 1993, and a freestanding cottage. Each room is done up with polished oak floors, crown moldings, mahogany furnishings, original Key West art, flat-screen TVs, and oversize verandas. Most rooms in the original are smaller (and less expensive), than those in the newer buildings, but the master suite has cathedral ceilings, a private balcony, Jacuzzi, and sauna. The free-form pool and outdoor bar are ideal for an after-hours swim and mojito, and the complimentary breakfast buffet stars Key lime beignets and extra-large muffins.

$199 or less
Editor's Pick
Key Lime Inn
725 Truman Avenue
Key West , Florida
33040
Tel: 800 549 4430 (toll-free)
Tel: 305 294 5229
keylime@historickeywestinns.com
www.historickeywestinns.com/properties/keylime/key_lime_inn.htm

This cluster of cottages a short stroll from Duval is the best of the seven hotels in the local association of Key West Historic Inns. The rooms are decorated in the style best described as Key West tropical: wicker furniture, Carmen Miranda–colorful bedspreads, choppy ceiling fans. The 37 rooms are spread out across various buildings and vary enormously: The smaller, less expensive ones are in the 1854 main house, which encircles the heated outdoor pool where breakfast is served. The suites in the bungalows are larger and more secluded and have a veranda well worth the extra cost. If you're driving down from Miami, the biggest plus is the free and ample on-site parking, a rare amenity in Old Town.

$400 or more
Editor's Pick
Hotel Photo
Little Palm Island Resort & Spa
28500 Overseas Highway
Little Torch Key , Florida
Tel: 305 872 2524
Tel: 800 343 8567
Fax: 305 872 4843
www.littlepalmisland.com

"Romantic and secluded," this resort consists of "individual bungalows on a well-manicured tropical island." There are no phones, TVs, or clocks in the rooms, but they do have four-poster beds and neutral color palettes. The Dining Room serves a blend of European and Latin dishes such as coriander-crusted elk or papas bravas. "Well-trained staff are "there when you need them but don't hover."

(30 rooms)

$300-$399
Editor's Pick
Hotel Photo
Marquesa Hotel
600 Fleming Street
Key West , Florida
33040
Tel: 800 869 4631 (toll-free)
Tel: 305 292 1919
marquesahotel@bellsouth.net
www.marquesa.com

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.

$200-$299
Editor's Pick
Hotel Photo
Old Town Manor
511 Eaton Street
Key West , Florida
33040
Tel: 305 292 2170
info@oldtownmanor.com
www.oldtownmanor.com

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.

$200-$299
Editor's Pick
Parrot Key Hotel & Resort
2801 N. Roosevelt Boulevard
Key West , Florida
33040
Tel: 888 665 6368 (toll-free)
Tel: 305 809 2200
info@parrotkeyresort.com
www.parrotkeyresort.com

If you don't mind being a short drive from Duval Street and the Old Town action, this quiet resort is made up of typical Conch-style bungalows set among lush tropical foliage and perfectly manicured walkways that wind through sculpture gardens and courtyard pools. Despite its location along strip mall–heavy Roosevelt Boulevard, the 118-room property has an isolated, escapist feel once you enter its inner sanctum. The colorful rooms have white linens and drapes accented with pops of turquoise, coral, and lime plus lots of local artwork. Some of the bungalows have a sandy area fronting the water, but you can't quite call them a beach, as there's no access for swimming—this is a prime boating area. For longer stays, consider upgrading to a two- or three-bedroom cottage. The largest of them rise to three stories and offer pretty water views. The downside is the lack of a proper restaurant (there's just a poolside café), so you'll be driving into town for dinner every night.—Terry Ward

$300-$399
Editor's Pick
Southernmost on the Beach
508 South Street
Key West , Florida
33040
Tel: 800 354 4455 (toll-free)
Tel: 305 296 6577
Fax: 305 294 2108
www.southernmostresorts.com/southernmost_beach.html

Right on the oceanfront of the island's south side, Southernmost on the Beach opened in 2008 where the legendary clothing-optional Atlantic Shores Resort once stood. Things are more tame these days, with the surrounds skewing family-friendly. But the vibe keeps with Key West's good-time feel, and the property is a very popular spot for weddings (yes, you'll hear the music from your room). The 123 guest rooms are contemporary (no tropical bedspreads), with dark mahogany furniture and muted colors. Second-floor rooms, particularly the full oceanfront spaces, offer more privacy. The hotel is one of the few in Key West with true beach access: South Beach is right here, and hotel guests can make use of complimentary lounge chairs. You can also hang out on the grassy lawn, which is outfitted with Adirondack chairs and hammocks. The quieter end of Duval Street is less than a block away, and you're just a short walk from the historic Old Town highlights.—Terry Ward

$400 or more
Editor's Pick
Hotel Photo
Sunset Key Guest Cottages
245 Front Street
Key West , Florida
33040
Tel: 800 937 8461 (toll-free)
Tel: 305 292 5300
Fax: 305 292 5395
westinsunsetkeycottages.com

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-, three- and four-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. 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.

Information may have changed since the date of publication. Please confirm details with individual establishments before planning your trip.