Harley Ray at Hog’s Breath Saloon
Experience the electrifying performance of Harley Ray at Hog's Breath Saloon, where his dynamic musical talents light up the Key West night. Set against the…
Free
36 events found.
entertainment
Events for February 22, 2026
Ongoing
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty at the Red Garter Saloon Stage in Rick's Entertainment Complex, Key West. Renowned for energizing mixes and captivating…
Free
Zach Lovering at General Horseplay
Zach Lovering captivates audiences with his dynamic musical talent at General Horseplay in Key West. Known for his engaging performances, Zach's energetic style complements the…
Free
DJ Chaka ~ Rick’s Bar Upstairs Stage
Experience an electrifying night with DJ Chaka at Rick's Bar Upstairs Stage. Renowned for energizing mixes and captivating beats, DJ Chaka transforms the dance floor…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the electrifying performance of the Alex Anthony Band at Hog's Breath Saloon. Known for their dynamic sound and engaging stage presence, the band brings…
Free
David Warren Band at The Bull & Whistle Bar
Experience an unforgettable evening with the David Warren Band at The Bull & Whistle Bar. Led by the talented David Bryce Warren, this lively band…
Free
DURTBAGS ~ Durty Harry’s Stage
Experience the ultimate Key West nightlife with The Durtbags at Durty Harry's Stage. Known as Key West’s biggest party rock band, they deliver electrifying performances…
Free
The Tiki Bombs at Tiki House Key West
Experience the vibrant sounds of The Tiki Bombs at Tiki House Key West. Known for their energetic performances and infectious tropical tunes, this dynamic band…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
Mike Stack & D-Lew at General Horseplay
Mike Stack & D-Lew bring their dynamic performances to the vibrant General Horseplay in Old Town Key West. Known for their engaging stage presence and…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke night at Rick's Bar Downstairs Stage in Key West. As the charismatic host, Jason brings unparalleled energy and entertainment,…
Free
Rolando Rojas at Sloppy Joe’s Bar
Rolando Rojas, a captivating and highly sought-after musician, electrifies Sloppy Joe's Bar with his exceptional guitar skills and charismatic stage presence. Known as a top…
Free
Harley Ray ~ Rick’s Downstairs Stage
Experience an electrifying night with musician Harley Ray at Rick's Downstairs Stage in Key West. Renowned for his captivating performances, Harley Ray brings a dynamic…
Free
Behind Bootleg at Sloppy Joe’s Bar
Experience the captivating sounds of Behind Bootleg at the iconic Sloppy Joe's Bar, a vibrant venue on Duval Street in Key West. Known for its…
Free
Mylo O’maolain at Schooner Wharf Bar
Mylo O'Maolain captivates audiences at the Schooner Wharf Bar with his soulful melodies and vibrant energy. This talented musician transforms the historic Key West venue…
Free
Big Bad Voodoo Daddy at Key West Theater
Join Big Bad Voodoo Daddy at the Key West Theater for an unforgettable night of swing and jazz. Known for their high-energy performances and exceptional…
$
Jon Hollywood at Tiki House Key West
Experience an unforgettable evening with Jon Hollywood at Tiki House Key West. Renowned for his captivating performances and magnetic stage presence, Jon delivers a vibrant…
Free
Belle and McKenna at Sunset Pier
Belle and McKenna, a dynamic musical duo, captivate audiences at Sunset Pier with their vibrant performances and eclectic repertoire. Their live music creates an unforgettable…
Free
David Warren at The Bull & Whistle Bar
Join the lively atmosphere at The Bull & Whistle Bar on Duval Street, where David Warren captivates audiences with his engaging live music performances. Known…
Free
801 Karaoke – Hosted by Jeff
Join the unforgettable Sunday karaoke at 801 Bourbon Bar, hosted by the charismatic Jeff. Known for his engaging personality, Jeff takes center stage, making each…
Free
Dan Harvey Duo at Hog’s Breath Saloon
Experience the captivating sounds of the Dan Harvey Duo at Hog's Breath Saloon, Key West. Dan Harvey, a talented musician, brings vibrant live music to…
Free
World Famous 801 Girls- 5pm Show
The World Famous 801 Girls captivate audiences with their dazzling performances at the lively 801 Bourbon Bar in Old Town Key West. Known for their…
QMitch Drag Queen Bingo at 22&Co
Experience an unforgettable night with QMitch Drag Queen Bingo at 22&Co in Old Town Key West. Renowned for dazzling performances and unmatched charisma, QMitch transforms…
Free
Sunday Jazz at the Gardens
Experience the soulful melodies of Sunday Jazz at the Gardens, where talented musicians serenade guests in the enchanting ambiance of The Gardens Hotel. Amidst lush…
Free
Sunset Celebration at Mallory Square
The Sunset Celebration at Mallory Square in Key West is a must-see event. Renowned street performers captivate audiences with their vibrant talents, creating an unforgettable…
Free
Jesse & Jillian at Schooner Wharf Bar
Experience the captivating sounds of Jesse & Jillian at Schooner Wharf Bar, where the dynamic duo brings their unique musical flair to Key West’s historic…
Free
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying beats of DJ Marty on the Red Garter Saloon Stage at Rick's Entertainment Complex. As the heart of Key West's nightlife scene,…
Free
Elle Haley at Tiki House Key West
Experience the captivating performance of musician Elle Haley at Tiki House Key West. Known for her soulful melodies and vibrant stage presence, Elle enchants audiences…
Free
Garrison Keillor And Erica Rhodes at Key West Theater
Join renowned entertainer Garrison Keillor alongside the talented Erica Rhodes at the Key West Theater for an unforgettable evening. Keillor, famed for his captivating storytelling…
$
Aaron Hudgins ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Aaron Hudgins at Rick's Bar Downstairs Stage in Key West. Known for his engaging presence, Aaron brings a dynamic…
Free
Sandra Lee at The Bull & Whistle Bar
Experience the captivating performance of musician Sandra Lee at The Bull & Whistle Bar in Key West’s Old Town. Renowned for her engaging live shows,…
Free
DJ Kori ~ Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Kori at Rick's Bar Upstairs Stage in Key West's vibrant nightlife scene. DJ Kori crafts an unforgettable musical journey,…
Free
DURTBAGS~ Durty Harry’s Stage
Experience the electrifying energy of The Durtbags, Key West’s ultimate party rock band, at Durty Harry’s Stage. Performing every Thursday through Sunday in the vibrant…
Free
Karaoke at Bobby’s Monkey Bar
Join the vibrant scene at Bobby's Monkey Bar in Old Town Key West for an unforgettable karaoke night. The spirited entertainer keeps the energy high,…
Naked Karate Girls at Sloppy Joe’s Bar
Experience the electrifying energy of the Naked Karate Girls, the ultimate party band hailing from Cincinnati. Known as The Best Band in the Galaxy, their…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable night of karaoke at Rick's Bar Downstairs Stage. Known for his infectious energy and dynamic hosting skills, Jason creates a…
Free