When John Huston directed his 1948 film Key Largo, he set his story in the Keys, though it would be 4 years before a town called “Key Largo” actually existed. After the success of the film, which starred Humphrey Bogart and Lauren Bacall, local businesses in Rock Harbor, Florida, lobbied the post office to change its name to Key Largo in 1952, unleashing a new and lasting wave of tourism.

Islamorada is not just the backdrop to, but a central character of, Netflix’s Bloodline television series (2015-2017), and nearly all filming was done on location in the Keys. One of the main sets, the Rayburn family home, is actually the Blue Charlotte House in The Moorings Village, and can be rented as a vacation home for $6,000 a night.

Many scenes from the 1989 James Bond film License to Kill were filmed in the Keys, including the opening aerial sequence, which took place above the Sugar Loaf Shores Airport. Today you can relive it in person with a tandem skydiving adventure that launches from the airport. Parts of 1994’s Drop Zone, starring Wesley Snipes, were also filmed there.

The colorful 2006 Real World house still stands in the Key Haven neighborhood just outside of Key West. The 6,000-square-foot, 10-bedroom palace can be rented as a vacation home for $3,000 a night. MTV took the cameras with them, however, so your vacation there will probably not turn into an international spectacle.

Famous in its own right, Ernest Hemingway’s former home has been a filming location for a number of films, including The Leisure Seeker (2017); it’s where Donald Sutherland’s character enjoys his last dance. It’s also just a few blocks from the southernmost terminus (Mile Marker 0) of the 2,370-mile U.S. Highway 1, and the Southernmost Point Buoy.

Another set from License to Kill, Timothy Dalton’s Bond parachuted onto the roof of this church. Some of the film’s other Key West locations include Garrison Bight Marina, Mallory Square, the Key West International Airport, and Thai Island, which was named the Barrelhead Bar in the film.

Just past the end of the road, you have to take a ferry ride to get to the swanky Sunset Key Cottages, a location for one of the final scenes in the cult comedy Office Space (1999). It’s Milton’s (Stephen Root) escape in the tropics, where the waiter brings him a piña colada, instead of the mai tai he ordered. A nice place to sip a cocktail and watch the sun set, before heading back north.