Most affordable time to travel: Most of November. The average weekly rate for two-bedroom properties during this time is around $1,672.
Peak time to travel: Late December and early January. The average weekly rate for two-bedroom properties during the peak season is around $4,200.
Vibe: Key West has at different times been the home of Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost, and Jimmy Buffett, among others. Dozens of galleries line the palm-filled streets of Key West, and attractions include Hemingway's former home, a designated literary landmark and museum.
Whether you're diving, fishing, golfing, or visiting its sidewalk cafes, open-air bars, legendary pubs, and delectable restaurants, travelers will be anything but bored here.
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