Key West Hotels Guide: Accommodations and Where To Stay in Key West, Florida

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Although the small, mom-and-pop guesthouse is still the quintessential Key West lodging experience, down here they've got it all, from old-time motels to upscale, full-service resorts. Average room rates are over $200 and in high season, anything below $125 is rare and below $90 is practically miraculous. Minimum stays may be required in some cases, especially in high season. Following is a selection of ten properties that cover most budgets and interests, all have pools unless otherwise noted.

Among luxury lodgings, those looking for some serious pampering in an elegant resort (100 very roomy and high-ceilinged suites), good dining, a spa, and a stellar waterfront location right on Mallory Square and the harbor, Ocean Key (Duval St. at Mallory Square; 305/296-7701 or 800/328-9815; www.oceankey.com) is definitely the ticket. Nearby, the slightly larger Pier House Resort (1 Duval St.; 305/296-4600 or 800/723-2791; www.pierhouse.com) has been an upscale favorite for years and with good reason – two very good restaurants, a full-service spa, and its very own stretch of beach. But if you really crave the quintessential Key West experience – a small, intimate guesthouse – stay at what is probably the most luxurious one in town. The Gardens (526 Angela St.; 305/294-2661 or 800/526-2664; www.gardenshotel.com) has 17 rooms in a 19th-century Bahamian-style mansion listed on the National Register of Historic Places.

On the upper end of our moderately-priced hotel choices is another historic property – the Marquesa Hotel (600 Fleming St.; 305/292-1919 or 800/869-4631; www.marquesa.com) is an award-winning small hotel (just 27 rooms) with the feel of an upscale B&B throughout an idyllic compound of four 1880s houses. On National Register of Historic Places is one of our top local favorites: the 28-unit Cypress House (601 Caroline St.; 305/294-6969 or 800/525-2488; www.cypresshousekw.com) is a distinctive Bahamian-style manse of weathered gray clapboard. Rooms are spacious and impeccable, and one of its social charms is the daily open-bar happy hour poolside (another is owner Dave Taylor's pair of endearing pups, Ben and Gabby). For something a bit larger with more services – not to mention very central, right in the Duval thick of things, the La Concha Crowne Plaza (430 Duval St.; 305/296-2991 or 800/745-2191; www.laconchakeywest.com) dates back to 1926 and is still the tallest building in town; its rooftop bar is a favorite for sunset-watchers.

Among budget options, small and still-shrinking is the pool of lodgings where you can bunk for $100 or less in season, but there are a few standouts. One is the Seashell Motel/Key West Youth Hostel (718 South St.; 305/296-5719; www.keywesthostel.com), lacking a pool but on a quiet street just steps from Higgs Beach. . With a choice of a bed in the clean, air-conditioned communal room or a private room (ten in number, with TV and fridge), it's among the best deals in town. In some ways an even stronger contender is a small, nine-unit compound of clapboard Conch cottages, also on the eastern side of town called Olivia by Duval (511 Olivia St.; 305/296-5169 or 800/413-1978; www.oldtownsuites.com/oliviabyduval). The reason boils down to the property's character: a gracious guesthouse feel and a cute little pool.

Finally, no Key West coverage is complete without mention of the many gay-owned and/or gay-popular lodgings down here, ranging from higher-temperature places catering to men or women only to "all-welcome" guesthouses where you wouldn't hesitate to bring grandma and the kids. One with a classy rep, beautifully landscaped grounds, mixed male-female clientele, and fairly moderate rates is Big Ruby's (409 Applerouth Lane; 305/296-2323 or 800/477-7829; www.bigrubys.com), flagship of a four-property chain extending to Costa Rica and France. If you want to take it all off where the boys are, the Island House (1129 Fleming St.; 305/294-6284 or 800/890-6284; www.islandhousekeywest.com) flaunts an elegant makeover yet still retains a distinctly frisky vibe, with 34 rooms from less than $100 year-round and day passes for non-guests (at the pool and bar/restaurant, there's quite the social scene). For the ladies only, check out the 38-room Pearl's Rainbow (525 United St.; 305/292-1450 or 800/749-6696; www.pearlsrainbow.com), also very tastefully decorated and clothing-optional, for a wide range of budgets but starting at less than $100 nightly.

Where to Stay: Elsewhere in the Keys
There are plenty of lodging options elsewhere in the Keys, from $70/night mom-and-pop motels to large full-service resorts. If your pockets are deep enough, we'd recommend several particularly upscale and well-regarded resorts as well worth an overnight or two (all with excellent spas). Two of the best are Islamorada's classy Cheeca Lodge (81801 Overseas Highway, Mile Marker 82, Islamorada; 800/327-2888; www.cheeca.com) and Hawk's Cay (61 Hawk's Cay Boulevard, Duck Key; 888/443-6393; www.hawkscay.com) on Duck's Key, an elaborate 60-acre resort with its own dolphin program and sailing school. More exclusive and off-the-beaten-path than either is Little Palm Island (28500 Overseas Highway, Little Torch Key; 800/343-8567; www.littlepalmisland.com), a five-acre private island off Little Torch Key with 30 gorgeous bungalow suites, superb service, beachside dining, and adorable miniature (and normally very elusive) Key deer freely roaming the premises.