Key West is the southernmost city in the continental United States, a small coral island at the very end of the Florida Keys and of U.S. Route 1. It lies about 210 kilometers (130 miles) southwest of Miami and roughly 150 kilometers from Cuba, and the island itself is only about 6 kilometers long and 2 wide.
Most visitors come for Old Town: streets of wooden houses on raised piers, Duval Street running from the Gulf of Mexico to the Atlantic, the sunset gathering at Mallory Square and the former homes of Ernest Hemingway and President Harry Truman. Getting there is part of the trip, along the Overseas Highway through the Upper, Middle and Lower Keys, past coral reefs, state parks and long bridges. Vacation rentals range from restored cottages and guest houses in Old Town to condos on the quieter east side, though short stays in the city are tightly regulated, so check a property's license before booking.
Old Town, the western part of the island, is where most visitors want to be. The Key West Historic District covers Duval Street, Mallory Square, the Truman Annex and Fort Zachary Taylor, and its restored cottages, conch houses and guest houses put restaurants, museums and the waterfront within walking or cycling distance. It suits couples and first-time visitors, though streets near Duval can be loud late at night.
The Casa Marina area, along the island's south shore, is quieter and more residential, with Higgs Beach, the White Street Pier and the West Martello Tower on its waterfront; it suits families and anyone who wants calm evenings within a short ride of Old Town. The newer neighborhoods on the east side of the island, closer to the airport, have more condos and townhouses with parking and pools, a practical choice for longer stays. Elsewhere in the Keys, Marathon, Islamorada and Key Largo offer larger rental homes, often on the water, at a slower pace.
The City of Key West regulates short-term rentals closely to protect housing for residents. Its licensing pages define a transient rental as a stay of 28 days or less, and renting a home or condo on that basis requires a city transient license, a Florida state license and a city business tax receipt. Transient use is allowed only in certain zoning districts, and the city caps the number of new transient licenses.
In practice, many houses in residential neighborhoods can legally be rented only for longer stays, while licensed guest houses, inns and some condos can take guests for a few nights. Before booking a short stay, ask the host to confirm that the property holds a valid transient license; the city publishes a map of licensed transient rental properties. Rules change, so check the city's current requirements too. Monroe County, which covers the rest of the Keys, has its own vacation-rental rules, so the same check is worthwhile in Marathon, Islamorada or Key Largo.
Many of Old Town's houses date from 1886 to 1912 and share a local style: wood-frame construction on piers about a meter above the ground, metal roofs and shuttered porches suited to heat and storms. Ernest Hemingway lived at his Whitehead Street house from 1931 to 1939, and six- and seven-toed cats, said to descend from one of his own, still roam the grounds. Harry Truman spent 175 days of his presidency at the Little White House in the Truman Annex.
Every evening, crowds gather on the waterfront at Mallory Square to watch the sun set over the Gulf. At the corner of South and Whitehead streets, a concrete buoy erected in 1983 marks the southernmost point of the continental United States and says 90 miles to Cuba, although the true distance is about 95 statute miles. Fort Zachary Taylor Historic State Park, around a Civil War-era fort near the island's southern tip, has a popular beach, and the Audubon House and the Martello towers add more history.
The Overseas Highway carries U.S. 1 for 113 miles, about 182 kilometers, from the mainland to Key West, crossing 42 bridges. In the Upper Keys, Key Largo is home to John Pennekamp Coral Reef State Park, which protects a long stretch of reef offshore. Islamorada, known for sport fishing, lies further south. In the Middle Keys, Marathon sits beside the Seven Mile Bridge; the modern bridge carries traffic, while a restored stretch of the old 1912 railroad bridge alongside, leading to Pigeon Key, is open to walkers and cyclists. The Lower Keys bring Bahia Honda State Park, with beaches and one of the deepest natural channels in the Keys, and the National Key Deer Refuge.
Offshore, the Florida Keys National Marine Sanctuary protects the Florida Reef, the only living coral barrier reef in the continental United States. About 68 miles, or 109 kilometers, west of Key West, Dry Tortugas National Park, reachable only by seaplane or boat, surrounds the massive brick Fort Jefferson with clear water and some of the least disturbed reefs in the Keys.
Key West's Spanish name, Cayo Hueso, means bone cay, and the island was inhabited by Native peoples long before Juan Ponce de León's expedition passed through the Keys in 1513. After Florida passed to the United States, Commodore Matthew Perry planted the U.S. flag here in 1822. Salvaging cargo from ships wrecked on the reef made Key West one of the wealthiest communities in the country in the 19th century, and Cuban exiles later brought a thriving cigar industry. The Overseas Railroad reached the island in 1912; after the 1935 Labor Day hurricane destroyed it, its roadbed and bridges became the highway.
Many early residents were Bahamian immigrants known as Conchs, a name locals still use. In 1982 a Border Patrol roadblock prompted the city's tongue-in-cheek secession as the Conch Republic. Writers from Hemingway to Tennessee Williams made the island home, and its festivals, including Fantasy Fest, keep its reputation for tolerance and fun alive.
Key West International Airport (EYW) lies about 3 kilometers east of the center; its relatively short runway limits aircraft size, so flights are mostly from Florida and other U.S. hubs. Many visitors instead fly into Miami International Airport (MIA) and drive the Overseas Highway, a trip of roughly three and a half to four hours without stops, with mile markers along the road counting down to Key West.
On the island, walking and cycling are the easiest ways to get around Old Town, where streets are narrow and parking is limited. A car is useful for exploring the rest of the Keys but can be more trouble than it is worth within Old Town. Cruise ships dock at the port beside Mallory Square, and boat tours leave from the historic seaport for snorkeling, sunset sails and the Dry Tortugas.
Key West has a tropical climate, warmer in winter than anywhere else in the continental United States, with a small difference between January, the coolest month, and July, the hottest. November through April is normally sunny and fairly dry, bringing only about a quarter of the year's rain, and it is the busiest and most expensive time to visit, so winter rentals are booked far ahead.
May through October is the wet season, with brief but heavy showers most days, and rainfall peaks between August and October, with September the wettest month. The Atlantic hurricane season runs from June to November; Hurricane Wilma in 2005 flooded much of the island and Hurricane Irma struck the Keys in 2017, so travel insurance and attention to official evacuation orders matter in late summer and autumn. Spring and early summer are a good compromise, with warm sea, longer days and fewer crowds.
Key West is about 130 miles (210 km) southwest of Miami by air and about 165 miles (265 km) by road. Driving the Overseas Highway usually takes three and a half to four hours without stops, longer in heavy traffic, and many travelers break the trip in Key Largo, Islamorada or Marathon.
Old Town suits first-time visitors who want to walk to Duval Street, Mallory Square and the museums. The Casa Marina area is quieter, near Higgs Beach. The east side has condos with parking and pools. For more space, consider a rental home elsewhere in the Keys.
Only if the property holds a City of Key West transient license, which is required for stays of 28 days or less, allowed only in certain zoning districts and capped in number. Many homes in residential areas may be rented only for longer stays. Ask the host to confirm the license, and check the city's current rules before booking.
November through April is sunny and dry and the most popular season. May to October is hotter and wetter, and the Atlantic hurricane season runs from June to November, peaking from August to October. Late spring often offers the best balance of weather and crowds.
Yes, though they are small compared with the mainland. Fort Zachary Taylor Historic State Park has a popular beach, and Higgs Beach lies along the south shore. Bahia Honda State Park in the Lower Keys and the reefs of the national marine sanctuary are the region's highlights for swimming and snorkeling.
Not within Old Town, which is compact, flat and easy to explore on foot or by bicycle, and where parking is limited. A car is useful for the drive down the Keys and for day trips to places like Bahia Honda State Park or the Seven Mile Bridge.
The famous buoy says 90 miles, but Key West and Cuba are about 95 statute miles (153 km) apart at their closest points. Havana itself is roughly 106 miles away, closer to Key West than Miami is by road.
Researched and written with AI assistance, then fact-checked against the sources below. Last checked .