Key West Theaters
Theaters in Key West: Plays, Musicals & Comedy Shows
Experience the vibrant entertainment scene with the best live theater performances in Key West! Delight in captivating musicals, hilarious stand-up comedy shows, engaging dramas, and unforgettable concerts—all set against the backdrop of a charming tropical paradise. From renowned venues like Red Barn Theatre and Waterfront Playhouse to intimate stages, our Key West Theater Directory ensures you'll discover top-rated shows perfect for every taste. Explore our listings, find your ideal event, and turn your island getaway into a memorable night out!
Red Barn Theatre
319 Duval St, Key West, FL 33040
(305) 296-9911
Experience the Magic of the Red Barn Theatre’s 45th Anniversary Season
For 45 years, the Red Barn Theatre has stood as a beacon of culture and creativity in Key West, offering intimate performances with Broadway-caliber excellence. This season, the Red Barn celebrates its rich history and enduring spirit with a stellar lineup of productions for 2024-2025:
THE FOREIGNER (Dec 18, 2024 - Jan 11, ...
Waterfront Playhouse
407 Wall St, Key West, FL 33040
(305) 294-5015
Experience the magic of live theater at the Waterfront Playhouse, a cultural gem in Key West’s historic Mallory Square. For over 80 years, this intimate 150-seat professional theater has captivated audiences with world-class productions, showcasing both local talent and renowned artists. Nestled just steps from Key West’s iconic sunset celebrations, the Playhouse is a must-visit destinatio...
Coffee Butler Amphitheater
21 Quay Rd, Key West, FL 33040
Nestled at Truman Waterfront near Fort Zachary Taylor, Coffee Butler Amphitheater offers an all-encompassing entertainment experience with stunning Gulf of Mexico views. Visitors can enjoy the world-famous Key West sunset while attending performances at this premier venue. The amphitheater features a grassy general admission lawn and intimate reserved seating against a one-of-a-kind panoramic back...
Comedy Key West
218 Whitehead St, Unit 5, Key West, FL 33040
Comedy Key West - Where Laughter Meets Paradise
Comedy Key West stands as the premier comedy destination in the Florida Keys, delivering side-splitting entertainment six to seven nights a week. Located at 218 Whitehead St, this intimate venue showcases world-class comedians from across the nation while nurturing local talent in a uniquely tropical setting.
Founded by comedy veterans Joe Madaus a...
Fringe Theater Key West
600 White St, Key West, FL 33040
Fringe Theater Key West: Expect the Unexpected
Discover Key West's community-focused theater at the historic Armory on 600 White Street. Since 2009, Fringe Theater has created unique opportunities for people to experience theater through education, outreach, and entertainment. The 2024-25 season features an exciting lineup of award-winning plays including the provocative "H*tler's Tasters," a fre...
Key West Theater
512 Eaton St, Key West, FL 33040
(305) 985-0433
The Key West Theater stands as a renovated performing arts center in downtown Key West, just one block from Duval Street. Built originally in 1848 as the First Baptist Church, this historic venue now delivers world-class performances including music concerts, comedy shows, and variety entertainment. Visitors can experience performances in the main stage theater featuring 278 seats with seated cock...
Tennessee Williams Theatre
5901 College Rd, Key West, FL 33040
Tennessee Williams Theatre: Key West's Cultural Jewel
The Tennessee Williams Theatre stands as a cultural anchor in the Lower Keys for over 44 years. Located on the campus of The College of the Florida Keys, this beloved venue brings together residents and visitors alike to share exceptional performing arts experiences. The theatre proudly hosts an impressive array of entertainment, from internat...
Tropic Cinema
416 Eaton St, Key West, FL 33040
The Tropic Cinema stands as Key West's premier independent theater, bringing quality films beyond mainstream blockbusters to this artistically diverse island community since 2004. This cultural gem features a distinctive aqua-blue Art Deco marquee, a Seward Johnson sculpture of Marilyn Monroe, and a Hollywood Walk of Fame with an island twist.
Inside, visitors discover a three-screen multiplex wi...
