One hundred and fifty miles south of mainland Florida, Key West floats at the end of the road as the southernmost point in the continental United States. An offbeat, come-as-you-are island, it’s long attracted writers, artists, drifters, and outdoorsmen drawn to its freedom and natural beauty. From afternoons fishing or snorkeling near the Gulf Stream to casual day drinking on legendary Duval Street and the nightly sunset celebrations at Mallory Square, Key West has a way of bewitching its visitors.
The charming Old Town district, lined with pastel “conch” cottages and Victorian-style mansions is also home to some of the island’s nicest resorts and historic inns that sit close to a whole host of great restaurants, bars, and attractions. But you’ll also find incredible hideaways in more off-the-beaten-path areas, from marina-front resorts on salty Stock Island to private cottages on Sunset Key and modern hotels across New Town. Read on for the best hotels to experience your own slice of Key West’s paradise.
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This guide was recently updated by Travel Writer Shayne Benowitz. At Time Out, all of our travel guides are written by local writers who know their cities inside out. For more about how we curate, see our editorial guidelines. While we might not stay in every hotel featured below, we've based our list on top reviews and amenities to find you the best stays. This article includes affiliate links. These links have no influence on our editorial content. For more information, see our affiliate guidelines.