Elle Haley at Hog’s Breath Saloon
Experience the captivating performance of musician Elle Haley at Hog's Breath Saloon, a vibrant venue in Key West's Mallory Square District. Elle fills the dive…
Free
38 events found.
entertainment
Events for February 21, 2026
Ongoing
Dan Harvey Duo at Hog’s Breath Saloon
Experience the electrifying performance of the Dan Harvey Duo at Hog's Breath Saloon in Key West. Known for their captivating tunes and vibrant energy, the…
Free
DJ Marty ~ Red Garter Saloon Stage
Experience the electrifying vibes of DJ Marty at the Red Garter Saloon Stage in Rick's Entertainment Complex. Known for his dynamic mixes and infectious energy,…
Free
David Warren Band at The Bull & Whistle Bar
Experience the electrifying performance of the David Warren Band at The Bull & Whistle Bar in Key West. Renowned for their dynamic stage presence and…
Free
DURTBAGS ~ Durty Harry’s Stage
Catch Key West's ultimate party experience with The Durtbags at Durty Harry's Stage! This electrifying rock band performs live every Thursday through Sunday at Rick’s…
Free
Tequila Time Machine at General Horseplay
Experience the electrifying energy of Tequila Time Machine at General Horseplay, where this captivating band transports you through musical eras with their dynamic performances. Nestled…
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,…
Trumastr at Tiki House Key West
Experience the captivating performance of Trumastr at Tiki House Key West! Known for his dynamic presence and exceptional musical talent, Trumastr creates an unforgettable atmosphere…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke night at Rick's Bar Downstairs Stage. Known for his infectious energy and captivating charisma, Jason transforms the evening into…
Free
Joe The Show at Sloppy Joe’s Bar
Experience the dynamic performance of Joe The Show at Sloppy Joe's Bar in Key West. Known for his engaging presence and musical talent, Joe captivates…
Free
Zack Seemiller ~ Rick’s Bar Downstairs Stage
Join musician Zack Seemiller at Rick's Bar's Downstairs Stage for an unforgettable evening of live music. Known for his captivating performances, Zack brings energy and…
Free
Sid The Bayou Kid at Sloppy Joe’s Bar
Sid The Bayou Kid, a charismatic musician from Thibodaux, LA, captivates audiences with his swamp-infused sound. With over 30 years of experience, Sid brings his…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell captivates audiences at the Schooner Wharf Bar in Key West with his vibrant live performances. Known for his engaging musical talents, Nick creates…
Free
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
Meghan Barter at Sunset Pier
Experience the enchanting melodies of musician Meghan Barter at Sunset Pier, where her captivating performance enhances the vibrant waterfront ambiance. Nestled in Key West's Ocean…
Free
Joe The Show at Tiki House Key West
Experience the unforgettable Joe The Show at Tiki House Key West, where this talented musician captivates audiences with his electrifying performances. Known for his dynamic…
Free
Derek Dunbar at The Bull & Whistle Bar
Experience the captivating sounds of Derek Dunbar at The Bull & Whistle Bar. Nestled in Key West’s vibrant Duval Street, this lively venue hosts Dunbar,…
Free
Bradd Shadduck ~ Rick’s Bar Downstairs Stage
Experience the captivating performances of musician Bradd Shadduck at Rick's Bar Downstairs Stage in Key West. Known for his engaging live music, Bradd's dynamic style…
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…
Sharese Nicole at Tiki House Key West
Experience an unforgettable evening with the talented musician Sharese Nicole at Tiki House Key West. Known for her captivating performances and soulful melodies, Sharese Nicole…
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
Sunset Blues w/ Andy Westcott at Sunset Pier
Experience the soulful sounds of Andy Westcott as he brings his Sunset Blues performance to Sunset Pier. With the backdrop of Key West's stunning sunsets…
Free
Jeff Clark Band at Sloppy Joe’s Bar
Experience the vibrant sounds of the Jeff Clark Band at Sloppy Joe's Bar, Key West's historic music hotspot since 1937. Jeff Clark captivates with his…
Free
Scallywagz Band at Schooner Wharf Bar
Experience the vibrant rhythms of the Scallywagz Band at the Schooner Wharf Bar. Known for their eclectic mix of island tunes and lively performances, the…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting performance of magician Frank Everhart at Schooner Wharf Bar in Key West's Seaport. With mesmerizing tricks and captivating showmanship, Everhart transforms this…
Free
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
Michael Corelto ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Michael Corelto at Rick's Bar Downstairs Stage. Known for his dynamic presence and captivating music, Michael brings the vibrant nightlife…
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
DJ at Hinote at General Horseplay
At the heart of Duval Street, DJ Hinote electrifies General Horseplay with captivating beats and infectious energy. Renowned for creating unforgettable nights, Hinote masterfully mixes…
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,…
Naked Karate Girls at Sloppy Joe’s Bar
Experience the electrifying Naked Karate Girls at Sloppy Joe's Bar, a must-see performance by Cincinnati's top band. Known as the best band in the galaxy,…
Free
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