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Duval Street

The streets of Key West aren’t just famous for the wild chickens that roam freely, they also offer a reflection of the things that make this place famous the world over, and Duval Street is the perfect example. Offering a famous watering hole that was once frequented by an equally famous resident and a variety of establishments that will allow visitors to play, observe, and marvel over the most beautiful and delicate creatures on earth, our RentTheKeys guests could spend a large portion of their Key West getaway on Duval Street and not feel as if they were missing out on anything important!

Sloppy Joes, 201 Duval Street

This local watering hole is known for the license plates lining its beams, the dollar bills stapled to the walls, and perhaps Key West’s most famous denizen, Ernest Hemingway, whose spot at the bar is still notated today! Step into history and enjoy a Florida favorite, the frozen Rum Runner, and party the night away listening to live entertainment in a place that has its own footnote in history.

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Red Barn Theater, 319 Duvall Street #2

Although New York is known for Broadway, a road filled with theaters offering high caliber plays, Key West also provides its own quality performances, with most being seen at the Red Barn Theater on Duvall St. Once a carriage house on a property built for the richest of Key West families, the building has gone through many incarnations over the years, including a stint as a barn for police horses, but today’s version is our favorite! Over the years, the works of famous writers and playwrights, Shel Silverstein and Tennessee Williams among others, have become the center of our cultural universe, and the tradition continues through today.

Run with the Bulls

Unlike the original Running of the Bulls in Pamplona, no one is hurt during this annual festival that takes place every July. The bulls are made from wood and the runners are dressed to resemble Papa Hemingway, in an event that is not surprisingly hosted by Sloppy Joes! Providing five days of shenanigans, fun, and games, this annual event represents the whimsical nature of Key West and will be an event your friends back home will turn green with envy over not being able to attend!

Shops, Restaurants, and More

The fun you can have on Duval St encompasses shops, restaurants, and the Key West Butterfly and Nature Conservatory, ensuring that your Key West adventures will be ones you never forget! And when you come home to RentTheKeys after a day on the street, your Florida getaway will be as close to perfect as possible. Reserve your favorite property today!