Key West Comedy Events
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Key West Comedy Events
Key West brings its island spirit to the stage with live music, open-air concerts, and laid-back performances happening daily. From local bands to touring acts, enjoy entertainment with a tropical twist. See what’s playing during your stay.
11/20/2026 - 11/21/2026
Dusty Slay
Dusty Slay, known for his distinctive laid-back storytelling and sharp wit, is set to perform at the Key West Theater. Slay has quickly become a favorite in the comedy circuit, captivating audiences with his unique perspective on everyday life. His S... Read more
Saturday, March 21, 2026 8:00 PM - The Reverend Peyton's Big Damn Band (21 and O
Sunday, March 22, 2026 8:00 PM - Tommy Emmanuel (21 & Over)
Wednesday, March 25, 2026 8:00 PM - Bumpin Uglies w/ Joey Harkum
All upcoming events are listed on this page. You can view all regular performing shows by visiting the Key West Shows page.