Key West Vacations

Key West vacations let you soak up the Florida sun while enjoying history, quirky local charm, and a dynamic social scene. A big bonus? Flip-flops count as formal wear here!

Major Attractions

There are several must-visit Key West attractions. The Ernest Hemingway Home and Museum (look for the estate's famed polydactyl cats) and the Harry S Truman Little White House, where the former President wintered, are historical gems. The Southernmost Point buoy on the corner of South and Whitehead streets is a great photo opportunity, and the Key West Butterfly and Nature Conservancy is a crowd-pleaser for all ages.

Key West is fairly easy to navigate; bike rentals are one way to get around. Still, many visitors discover it's helpful to line up car rentals in Key West. You may wish to cross the Seven Mile Bridge and check out Marathon Key. If you're visiting in a hotter month, you'll appreciate being able to hop into an air-conditioned rental car rather than pedaling from spot to spot.

Festivals and Events

Your Key West visit will definitely correspond with one favorite local event: The Key West Sunset Festival, held nightly at Mallory Square. The Key West Fishing Tournament runs from April through November; submit proof of your catch and receive a certificate and possibly a prize. Speaking of seafood, celebrate the beginning of lobster season in early August during Key West Lobsterfest. Unquestionably, the most anticipated annual event is Fantasy Fest, held the last weekend in October. It's like Mardi Gras, island style. Regardless of when you visit, concierges at Key West hotels can give you a rundown of what's on the calendar during the week or weekend of your visit.

Browse Travelocity's Key West packages and save up to $537 when you book your hotel and flight at the same time. Why not rent or charter a sailboat with the money you'll save on Key West vacation packages?

Guide to Exploring Key West

Top Hotel Deals

See all Key West hotels
1.0 out of 5.0
1.5 out of 5.0
2.0 out of 5.0
2.5 out of 5.0
3.0 out of 5.0
3.5 out of 5.0
4.0 out of 5.0
4.5 out of 5.0
5.0 out of 5.0
Most popular package deals found by our travelers
Most popular package deals found by [originCity] travelers

Top Flight + Hotel Deals

See all Key West packages

Top Deals on Flights

Book a Vacation to Key West