Elle Haley at Hog’s Breath Saloon
Experience a captivating evening with Elle Haley at Hog's Breath Saloon in Key West's vibrant Mallory Square District. Known for her mesmerizing performances, Elle brings…
Free
41 events found.
entertainment
Events for February 14, 2026
Ongoing
Alex Anthony Duo at Hog’s Breath Saloon
Experience the dynamic performance of the Alex Anthony Duo at the iconic Hog's Breath Saloon in Key West. Known for their electrifying live music, Alex…
Free
DJ Marty ~ Red Garter Saloon Stage
Experience the vibrant beats of DJ Marty at the Red Garter Saloon Stage in Rick's Entertainment Complex, Old Town Key West. Renowned for his electrifying…
Free
LuffKiD at General Horseplay
Experience the magnetic energy of LuffKiD at General Horseplay in Old Town Key West. Known for his captivating performances, LuffKiD brings an electrifying blend of…
Free
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Duke at Rick's Bar Upstairs Stage, where this dynamic DJ sets the night ablaze with his unparalleled mixing skills.…
Free
Chase Shepard Band at The Bull & Whistle Bar
Experience the dynamic energy of the Chase Shepard Band at The Bull & Whistle Bar in Key West. Known for their captivating performances and musical…
Free
DURTBAGS ~ Durty Harry’s Stage
Experience the electrifying performances of The Durtbags, Key West's premier party rock band, at Durty Harry's Stage. Enjoy their captivating live shows every Thursday through…
Free
Tequila Time Machine at General Horseplay
Experience the electrifying sounds of Tequila Time Machine at General Horseplay in Key West. This dynamic band delivers an unforgettable night of music, perfectly complementing…
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,…
Riptide Riot at Irish Kevin’s Bar
Riptide Riot electrifies the stage at Irish Kevin’s Bar in Key West’s Old Town. This dynamic band captivates audiences with their high-energy performances and engaging…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an electrifying karaoke night at Rick's Bar Downstairs Stage in Key West's largest entertainment complex. Jason's dynamic energy and engaging stage presence…
Free
Justin Angelo at Sloppy Joe’s Bar
Justin Angelo, a rising star known in the Lancaster, PA, and Key West music scenes, captivates audiences at Sloppy Joe's Bar with his unique blend…
Free
Jeff Harris at Irish Kevin’s Bar
Experience the vibrant sounds of Jeff Harris at Irish Kevin’s Bar, where his electrifying performances captivate audiences amid Key West’s Old Town. Known for his…
Free
Zack Seemiller ~ Rick’s Bar Downstairs Stage
Experience the captivating musical artistry of Zack Seemiller at Rick's Bar Downstairs Stage. Known for his dynamic performances and engaging presence, Zack delivers an unforgettable…
Free
Ross Brown at Sloppy Joe’s Bar
Ross Brown, a talented musician based in Key West, FL, captivates audiences at Sloppy Joe's Bar with his masterful guitar, percussion, and vocal skills. Performing…
Free
Nick Brownell at Schooner Wharf Bar
Nick Brownell brings his musical talents to the Schooner Wharf Bar, captivating audiences with his lively performances amidst the picturesque surroundings of Key West's Seaport.…
Free
Joe The Show at Tiki House Key West
Experience the incredible talent of Joe The Show at Tiki House Key West. Known for his electrifying performances and musical prowess, Joe captivates audiences with…
Free
Derek Dunbar at The Bull & Whistle Bar
Experience the captivating musical talents of Derek Dunbar at The Bull & Whistle Bar in Key West’s vibrant Old Town. Known for his electrifying performances,…
Free
NY Pauly at Irish Kevin’s Bar
Experience the dynamic performance of NY Pauly at Irish Kevin's Bar! Renowned for his engaging live music and energetic crowd interaction, NY Pauly captivates audiences…
Free
Bradd Shadduck ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of musician Bradd Shadduck at Rick's Bar Downstairs Stage, where his engaging melodies and dynamic presence light up the venue. Nestled…
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…
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 takes the stage at Sunset Pier in Key West. With his captivating blues performances, Andy brings…
Free
Jerico Duo at Sloppy Joe’s Bar
Experience the electrifying performance of the Jerico Rockabilly Duo at Sloppy Joe's Bar. Known for their captivating rockabilly tunes, the duo promises a lively and…
Free
Elle Haley at Tiki House Key West
Experience an unforgettable evening with Elle Haley at Tiki House Key West. Known for her captivating performances and musical talent, Elle brings a unique blend…
Free
Irish Kevin at Irish Kevin’s Bar
Experience the infectious energy of Irish Kevin at Irish Kevin's Bar in Key West's Old Town. As a charismatic musician, Irish Kevin captivates audiences with…
Free
Adrienne Z Band at Schooner Wharf Bar
Experience the captivating performance of the Adrienne Z Band at Key West's iconic Schooner Wharf Bar. Known for their soulful sound and dynamic stage presence,…
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. Known for his dynamic mixes and vibrant energy,…
Free
Zach Lovering at General Horseplay
Zach Lovering captivates audiences at General Horseplay, infusing the lively cocktail bar with his dynamic musical performances. Known for his engaging presence and vibrant sound,…
Free
Ray Fogg And Reese Dailey at Key West Theater
Join renowned musician Ray Fogg at the Key West Theater for an unforgettable evening of live music. Known for his engaging stage presence and impressive…
$
Michael Corelto ~ Rick’s Bar Downstairs Stage
Experience the captivating talent of Michael Corelto at Rick's Bar Downstairs Stage in Key West's vibrant entertainment complex. Known for his electrifying performances, Corelto brings…
Free
DJ Chaka ~ Rick’s Bar Upstairs Stage
Experience the electrifying beats of DJ Chaka at Rick's Bar Upstairs Stage in Key West. Known for his dynamic soundscapes and vibrant mixes, DJ Chaka…
Free
DJ at Hinote at General Horseplay
Experience electrifying sets from the talented DJ at Hinote at General Horseplay. Known for their dynamic mixes and infectious energy, this DJ turns the vibrant…
Free
Chase Shepard Band at The Bull & Whistle Bar
Experience the electrifying Chase Shepard Band live at The Bull & Whistle Bar, Key West’s iconic nightlife spot. Dive into a night of energetic performances,…
Free
DURTBAGS ~ Durty Harry’s Stage
Experience the ultimate Key West nightlife with The Durtbags, the island’s premier party rock band, lighting up Durty Harry's Stage at Rick's Entertainment Complex. Catch…
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,…
LaurLea & Tripp Fabulous at Sloppy Joe’s Bar
Experience the electrifying performance of LaurLea & Tripp Fabulous at Sloppy Joe's Bar in Key West. This Philadelphia-based party rock band takes the stage from…
Free
Mike Stack & D-Lew at General Horseplay
Join Mike Stack & D-Lew at General Horseplay in Old Town Key West for an unforgettable night of live music. Known for their energizing performances…
Free
Jack and Jim at Irish Kevin’s Bar
Experience the electrifying duo Jack and Jim at Irish Kevin’s Bar in Key West. Known for their dynamic performances, they engage audiences with lively music…
Free
Cachete at Tiki House Key West
Experience the vibrant rhythms of Cachete at Tiki House Key West. This talented entertainer brings an infectious energy and captivating performance style that will leave…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke night at Rick's Bar on the Downstairs Stage. As a charismatic entertainer, Jason brings energy and excitement, transforming the…
Free