Where to Attend a Drag Show in Key West

As an internationally known LGBTQ+ travel destination, Key West Florida is celebrated for its inclusivity and openness. Among its many treasures, Key West boasts a dazzling drag show scene that is not to be missed. Attend a drag show in Key West and experience a night of comedy, glamour, costumes, entertainment, and laughter at Aquaplex, 801 Bourbon Bar, Mangoes, or La Te Da. Come as you are in and stay with Rent Key West Vacations, a proud Key West Business Guild member, a nonprofit organization promoting LGBTQ+ travel in the Keys!

Aquaplex Key West

Aquaplex offers drag shows every night in Key West! Attend a show at Aqua Bar and Night Club and witness the Aquanette’s showstopping drag performance. Aquaplex is also home to the island’s newest live act, The Birdcage Cabaret. See drag icon Christopher Peterson take the stage and show off impersonations while singing and lipsyncing with various local performers, female singers, and jugglers. 

801 Bourbon Bar

Visit 801 Bourbon Bar and attend the longest-running drag show in Key West at 9 pm or 11 pm nightly. Meet the 801 Girls and expect a night of beauty and comedy with a variety of talented entertainers!


Mangoes hosts a special Sunday Drunken Drag Brunch once a month that is not to be missed. Plan your getaway around one of these fabulous brunches and experience Drag Queen performances, a live DJ, bottomless mimosas, specialty cocktails, and a la carte brunch food. Purchase tickets for upcoming events and proceeds will be donated to local charities. 

La Te Da

Make your way to the La Te Da hotel and attend the Randy Roberts Live Cabaret show during your time in Key West. With over three decades of experience, Randy Roberts presents a classic drag show with live vocals, stunning costumes, and impersonations. Purchase tickets to the Tuesday, Friday, Saturday, or Sunday shows starting at 8 pm!

Welcoming Everyone to Our Key West Vacation Rentals 

Check out the bustling nightlife scene during your visit and purchase tickets to one of the drag shows in Key West. Book your getaway with Rent Key West Vacations and find the perfect Key West vacation rental for your unique needs. For assistance customizing your Key West vacation, please contact us at 1-800-833-7368. 

The Best Bars in Key West to Visit on Vacation

Key West is famous for its sunsets, turquoise waters, white sand beaches, rich history, and lively nightlife. Escape to the southernmost point in the U.S. with Rent Key West Vacations and check out the island’s top attractions during your visit. Make your way to Duvall Street and discover the best bars in Key West, offering refreshing cocktails, live music, happy hours, and local history. Whether you want to grab a drink at Ernest Hemingway’s favorite watering hole or catch the sunset at a bar along Mallory Square, there is a destination for everyone:

Sloppy Joe’s

Visiting the historic Sloppy Joe’s is a must during your Key West vacation. This bar has been a Key West tradition since 1933 and is famous for being Ernest Hemingway’s favorite watering hole. Hang out in a piece of Key West history and grab a drink at Joe’s Tap Room, serving craft beer and tasty cocktails. Joe’s also offers one of the best parties in town, with live music daily from noon to 2 a.m.

Green Parrot Bar

Another Key West icon, the building of the Green Parrot Bar, started as a grocery store in the 1890s, turned into a dive bar after WWII, and was renovated in the 1970s as the Green Parrot Bar. Today, the bar is a favorite destination for live music on the island, with live local musicians taking the stage multiple times daily.

Irish Kevin’s

Visit Irish Kevin’s on Duval Street for a classic Irish pub experience in the Keys. Enjoy unique cocktails like the world-famous Green Gator, featuring lemon rum, blue curacao, oj, sour mix, and 151 floaters in a souvenir glass. Stop in for live music, drinks, burgers, sandwiches, and delicious Key Lime pie!

Captain Tony’s Saloon

Captain Tony’s Saloon was the original location of Sloppy Joe’s Bar, located directly across the street. This historic saloon was the favorite watering hole for celebrities like Ernest Hemingway, Truman Capote, Tennessee Williams, and Jimmy Buffet. Unique pieces of Key West history are found all over the bar, including the stools painted with famous visitors’ names.

Sunset Pier

If you are looking for a Key West bar to watch the sunset over the water, we recommend visiting Sunset Pier near Mallory Square. Enjoy live music, tropical drinks, breathtaking sunset views, and delicious seafood. 

Key West Vacation Rentals near Duval Street

Book your getaway with Rent Key West Vacations and stay close to the action with our vacation rentals in Old Town. Properties like Ann Street Cottage, Tranquility, and Namaste put you minutes away from the best bars in Key West. Stay within one block of Duval Street and two blocks from famous bars like Sloppy Joe’s, The Bull, and Hog’s Breath. To customize your vacation, please call our reservation specialists at 1-800-833-7368.