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Key West

Key West Vacations

Key West hangs - or, more often, swings - like a dazzling, off-beat and gaudy pendant at the southernmost point of the continental US. But its semi-detachment is more than geographic; it's part of the laissez-faire that - along with the subtropical climate and palm-shaded streets - has attracted artists, musicians, writers and a thriving gay community.

Region: Florida Keys

Featured Key West Hotel

Casa Marina, A Waldorf Astoria Resort

Casa Marina, A Waldorf Astoria Resort

Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.
Key West

Nestled along the southern edge of Key West, this resort overlooks more than 1,100 feet of beach reserved exclusively for hotel guests.

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It's practically impossible not to fall in love with the tropical nights, Bahamian architecture and warm people. Get off the beaten path and sample life in the Conch Republic.

What To Do

Generally if bar hopping isn't on the itinerary, laying around on a comfy stretch of sand will be. There are three city beaches on the southern side of the island: City Beach and Higgs Beach are more family-oriented, while Smathers Beach is popular with the jet skiing and parasailing 'vroom' crowd.


Any day is a good day for a festival as far as Key Westerners are concerned. By far the most bizarre is the Hemingway Days Festival in July, when 150-plus 'Papa' look-alikes converge on Sloppy Joe's Bar. Festivities strike a balance between the high- and low-brow; there are readings and short-story contests, as well as the Key Lime Pie-eating competition and the distinctly Key Western version of 'running of the bulls'.

Other notable festivals include: PrideFest, a huge June celebration of the city's gay population (almost 30% of the total); October's huge ten-day Fantasy Fest - a cross between Carnivale and Halloween but with much more nudity; the Conch Republic Independence Day in April/May, which commemorates the 'secession' of the Keys from the US; the Goombay Festival, held in October, which celebrates Bahamian culture; and the Annual Key West Literary Seminar draws top-notch writers from afar in January.