Hotels in Key West

Key West: Southernmost City on the US mainland

Key West sits at the end of the Florida Keys, 160 miles southwest of Miami and just 90 miles north of Cuba. The island measures roughly 4 miles long and 2 miles wide, making nearly every hotel walkable to the water. The city became a formal US territory in 1822 and by the 1890s was Florida's most populated city, built on cigar manufacturing and wrecking salvage. Ernest Hemingway lived on Whitehead Street from 1931 to 1939, and his house remains one of the most-visited addresses in the Keys.

Where to Stay in Key West

Most visitors base themselves along Duval Street or in the Old Town district, where converted conch-style cottages and small inns cluster within walking distance of Mallory Square and the nightly sunset celebration that has drawn crowds since the 1960s. The Truman Annex neighborhood, anchored by the Harry S. Truman Little White House, offers quieter streets one block from the waterfront. Hotels range from guesthouses with fewer than 10 rooms to full-service resorts on the Atlantic side.

Practical Tips

• Getting there: US-1 (the Overseas Highway) is the only road in; allow 3–4 hours from Miami in peak season traffic.
• Parking: Scarce and expensive in Old Town — most guests park once and walk or rent bicycles.
• Weather: Hurricane season runs June through November; January through April sees the driest, coolest conditions.