Key West Vacation Deals

Closer to Havana than it is to Miami, Key West is the southernmost city of the continental United States, approximately 90 miles (140 kilometers) from the Cuban capital. Key West refers to the island as well as the city. Over the years, it has been a pirate refuge, a naval base and a favored haunt of American literary legends, including Ernest Hemingway. Today, the island appears to be in permanent vacation mode, with plenty of bars, restaurants and beaches where you can while away the hours.

Make your first stop at the impressive monument at the corner of South and Whitehead streets near South Beach. Proudly announcing in bold letters that you are at the southernmost point of the continental United States, it is one of Key West’s most photographed attractions. 

Most of the tourist attractions are located in the old town. Step inside the Key West Shipwreck Museum, which charts the history of the “wreckers” who used to rescue people from sunken ships then salvage the cargo.

Visit the Ernest Hemingway Home and Museum, a Spanish colonial-style building in which the author wrote some of his most famous works. At Ripley’s Believe It or Not! Odditorium, see Hemingway’s typewriter, glasses and a shrunken human torso that he owned. The Harry S. Truman Little White House is a historic site where the former president made many decisions on domestic and foreign policy.

Join locals and visitors who gather every evening at the water’s edge at Mallory Square for the sunset celebration. Street performers and exhibitors entertain the crowds as the sun lowers into the Gulf of Mexico.

Duval Street is downtown Key West’s main strip and home to the majority of pubs, restaurants and nightclubs.

At 4 miles (6.4 kilometers) long and 2 miles (3.2 kilometers) wide, Key West is not a big city. Most people spend their time in the old town, where all the attractions are within easy walking distance. Bicycles and scooters, which can be rented, are popular ways to get around.

For more details on interesting local attractions and activities, check out our things to do in the Florida Keys page.

Popular Activities in Key West

Vacations are pretty great already. But taking advantage of the fantastic activities on offer always makes them better!

Key West has loads of activities. Here are some ideas to get you started:

• Key West Discovery Helicopter Flight
• Bugeye Backcountry Eco Tour
• Key West Ultimate Sights Helicopter Tour
• Key West Icons & Landmarks Helicopter Flight
• Urban Adventure Quest - Key West
• Backcountry Kayak & Stand-Up Paddleboard Tour

For more options, go to our Key West things to do page.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.