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While we do our best to ensure the accuracy of our listings, some venues may be currently temporarily closed without notice. Please confirm status on the venue website before making any plans.

Best Entertainment in Key West

By: Cityseeker
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The Piano Bar at La Te Da

The Piano Bar at La Te Da is for those who want to have an entertaining time without any pretense. This lively watering hole and entertainment spot will keep you in splits with their hilarious shows. Be the funny antics of Dave Bootle, Christopher Peterson's fabulous impersonations, drag shows and cabaret, you will enjoy the night with these engaging acts and good drinks.

Key West, FL, United States
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801 Bourbon Bar and Cabaret

Welcome to the world of gay adult entertainment! Part of the famous Bourbon Street Pub Complex, 801 Bourbon Bar and Cabaret features Sushi and 801 girls who entertain with world-famous drag shows. Head straight to the bar downstairs after a night show, visit the Bourbon Street Pub—the popular gay dance bar next door or just browse through other interesting joints in the Bourbon Street Pub Complex.

Key West, FL, United States
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Key West Theater

Built in 1848, the Key West Theater changed several hands and has been a church, a concert venue and even a nightclub over the years. Now one of the most important cultural centers, the theater is a must-visit for anyone who wants a glimpse of the local theater scene. Plays, live musical events, dance performances and even standup comedy nights take place here often. While enjoying the show, spectators can also call for cocktails to be brought to their seats. If you want to immerse yourself in the local culture, do so by checking out the schedule of Key West Theater and heading there for a show.

Key West, FL, United States
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Green Parrot Bar

Wild groups gather at this open-air bar nightly, to party 'til they drop. If you are up for a pretty rambunctious scene, you will enjoy this antique saloon built in 1890 and generally agreed upon as the oldest bar in Key West. The co-owned smokehouse next door called "Meteor," serves pork, chicken, beef and seafood until 2am. Play pool, darts, or pinball while trying a "spine-tingling" cocktail. On weekends, there is live music, and the jukebox pounds out blues, zydeco and reggae all week. Don't miss this spot, listed as one of the "World's 50 Greatest Bars."

Key West, FL, United States
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Waterfront Playhouse

Named "The Best Professional Theater in Florida" by Florida Monthly Magazine in 2010 and 2011, The Waterfront Playhouse is a not-for-profit, professional theater located on historic Mallory Square in Old Town Key West. The theater attracts locals and tourists alike with a wide range of comedies, dramas, musicals, concerts, and world premieres. The Playhouse utilizes Key West's rich talent pool of actors, directors and designers, as well as attracting internationally known luminaries.

Key West, FL, United States
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Tennessee Williams Theatre

Nestled in the sprawling campus of the Florida Keys Community College, the Tennessee Williams Theatre is a center dedicated to different forms of art genres. This venue is a huge art complex that features three spaces including an auditorium, foyer and outdoor stage. It hosts multitude of events throughout the year and each season it brings forth innovative and interesting shows. Dance performances, concerts, comedy shows, poetry reading sessions, cabaret, workshops, rehearsals and the list of gigs held here is endless. For additional information and schedule, check its website.

Key West, FL, United States
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