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In Key West, 10 Places to Sleep Tight

By Andrea Sachs
Washington Post Staff Writer
Sunday, January 15, 2006

Key West has -- hang onto your slippers -- 3,881 hotel rooms and 908 B&B guest rooms, according to the Florida Keys and Key West Tourism Council. Accommodations range from garden guesthouses to Old South manses to same-sex quarters.

To save you the grief of hopping from bed to bed in search of the perfect fit, we vetted 10 properties that stand out amid the overcrowded sleeper scene. Here are our picks, which cover a variety of budgets and are mainly central to the Duval Street action. Rates listed are the lowest available per night and are for double rooms. During special events such as October's Fantasy Fest and winter holidays, prices can rise by 20 percent or more.

· So many properties claim to sit on the most southern point of the United States. However, if you pull out the yardstick, the true honor goes to the exquisite Southernmost House Grand Hotel . The pink-turreted mansion has 12 rooms befitting a president -- which makes sense, since the 1896 house has hosted a number of chief executives and doubles as a museum of presidential and Hemingway memorabilia. Besides the hotel's southernmost pet rabbits, it also has the southernmost bar where you can order a southernmost cocktail and sip it at the southernmost pool.

1. 400 Duval St. Rates from $155. Info: 866-764-6633,http://www.southern mosthouse.com.

· At the Key West Youth Hostel , you'd be wise to abide by the rules: "Place your name tag on your bed. No name tag, no sleep," reads a sign posted on the front door. If you're not into the "Hello My Name Is" scene -- or, more specifically, sleeping with a roomful of strangers -- you can stay in a private room at the affliated Seashell Motel , just across the courtyard. The 10 hotel rooms are so stripped down that we had to use shampoo for soap (or maybe we were supposed to put our name on the bar?). And while there's no pool, the outdoor common area is quite the social center, with its open-air kitchen and rotating band of foreign travelers. The hostel/hotel is a short trek to Duval Street, but those backpackers are used to hoofing it.

718 South St. Hostel rates, $34; hotel rooms, from $95. Info: 305-296- 5719, http://www.keywesthostel.com/ .

· Look around Pearl's Rainbow and you'll notice something's missing: men. That's because the property is for women only and is female-friendly, regardless of sexual orientation. The 38-room sanctuary has two pools, an outdoor bar and grill, a dining room serving breakfast and dinner (open to the public, but again, no Y chromosomes allowed) and a Friday happy hour for visiting and local women. On the way out, pay respects to the elegant portrait of the guesthouse's namesake, a bon vivant and lover of all women.

525 United St. Rates from $99. Info: 800-749-6696,http://www.pearls rainbow.com. For a list of all-male accommodations, see http://keywest.com/gayaccomm.html.

· At the Speakeasy Inn , smoking is not allowed in the four eye-pleasing white-and-wood rooms -- despite the temptation of the Key West Havana Cigar Co. below (the store is also the lobby). However, guests can light up on the balcony, whose railing is carved with bottles, hearts and diamonds, a tacit sign for gambling and drinking during Prohibition. The store is a mini-museum of cigar artifacts and folk art, as well as a hangout for Key West's colorful cronies, including 90-year-old Tony Barcelo, a Hemingway drinking pal, and Mr. King, who plays the hand saw. It's a veritable Key West Social Club.

1117 Duval St. Rates from $65. Info: 305-296-2680,http://www.speakeasy inn.com.

· At the 100-room Ocean Key Resort and Spa, enjoy Mallory Square's evening carnival of kooks . . . in your bathrobe. The hotel's dockside location offers prime views of the spectacle -- and legendary sunsets -- from the comfort of your balcony or, if you prefer, from a table on Sunset Pier or a cushy chaise longue by the pool. The party-size guest rooms are splashed with bright colors and prints that are one part preppy, two parts Caribbean. But the bathroom is solid luxury; the bubbly tub opens up to the bedroom and the sea and sky beyond.

Zero Duval St. Rates from $179. Info: 800-328-9815,http://www.oceankey.com .

· Literati types can sleep among the classics at the Author's Guesthouse , where most of the 10 rooms and two cottages are named after English Lit faves, such as Lillian Hellman, Thornton Wilder and Carson McCullers. The decor also reflects each master's works, so the Tennessee Williams cottage, for example, has an old Underwood and a framed Playbill of "Cat on a Hot Tin Roof." The property is in a quiet residential neighborhood, allowing guests to catch up on their reading in the courtyard.

725 White St. Rates from $80. Info: 800-898-6909,http://www.authorskey west.com.

· No matter how late you party or how many cocktails you imbibe, stay at the 150-room La Concha and your head is guaranteed to find its pillow -- even if you can't actually feel your head. The Crowne Plaza hotel sits smack in Party Central, on lower Duval Street. And while the 1926 spot has history aplenty-- Hemingway stayed at La C and Tennessee Williams completed "A Streetcar Named Desire" here -- more importantly, it has the Top. The seventh-floor lounge and observation deck is the place to warm up for an evening out, starting with a rum runner and a toast to the dipping sun.

4 30 Duval St. Rates from $129. Info: 800-745-2191,http://www.laconcha keywest.com.

· For divers who want little separation between scuba and sleep, Captain's Corner Dive Shop offers simple accommodations to visitors enrolled in the center's underwater courses. The two dorm rooms are a quick skip from the classroom, onsite training pool and scuba store. Amenities are basic -- bunk beds, communal fridge and microwave -- but that should hardly matter to those who will be spending more time on sea than on land.

125 Ann St. Rate is $30 a night, plus course fees. Info: 305-296-8865,http://www.captainscorner.com.

· Don't believe the rumors: Oprah does not live on Sunset Key. But as a Hilton Key West Resort & Marina guest on the secluded 27-acre island, no one needs to be the wiser. In addition to its 187-room property on Key West, the resort also offers 37 two- and three-bedroom cottages on the island occupied by the super-flush and accessible only by launch. Non-island guests can loaf on the white-sand beach (a rarity) and swim in the pool with a $20 day pass ($40 for everyone else). But only cottage "residents" can have the privilege of saying they slept on the same island as . . .

245 Front St. Cottages from $595. Info: 305-292-5300,http://www.sunsetkey cottages.hilton.com.

· One-up your friends who brag about ocean views by staying on the water in a houseboat. Granted, the houseboat does not move; it's more like a floating home that roosts on the dock. Each of the four houseboats has two bedrooms (a pair of queens and a single), a full kitchen and a dock "yard." The Harborside Motel & Marina is on Garrison Bight, a big sportfishing hub, so if you act neighborly, you just might get a fresh catch for lunch.

903 Eisenhower Dr. Rates from $129 per night for two. Info: 800-501-7823,http://www.keywestharborside.com.

For other accommodations , see the Key West tourist office's Web site, http://www.fla-keys.com/keywest/placestostay.htm.

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