Dan Harvey at Hog’s Breath Saloon
Dan Harvey, a talented musician, captivates audiences at the vibrant Hog's Breath Saloon in Key West's Mallory Square District. Known for his engaging performances, Dan…
Free
38 events found.
entertainment
Events for February 27, 2026
Ongoing
DJ Marty ~ Red Garter Saloon Stage
Experience the energetic beats of DJ Marty at the Red Garter Saloon Stage, nestled within Rick's Entertainment Complex in Key West. Renowned for his electrifying…
Free
Hot Girl Bummer at General Horseplay
Experience the electrifying performance of Hot Girl Bummer at General Horseplay, where vibrant live music meets inventive craft cocktails. Located in the lively heart of…
Free
DJ Chaka ~ Rick’s Bar Upstairs Stage
DJ Chaka electrifies the Upstairs Stage at Rick's Bar in Key West's premier nightlife destination. Known for dynamic beats and infectious energy, DJ Chaka transforms…
Free
DURTBAGS~ Durty Harry’s Stage
Experience the ultimate party with The Durtbags, Key West’s premier rock band, at Durty Harry’s stage. Every Thursday through Sunday, they deliver electrifying performances that…
Free
Karaoke with Foss at RockHouse Live
Experience an unforgettable night of entertainment with Foss at RockHouse Live in Key West. Known for electrifying performances, Foss brings charisma and energy to the…
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,…
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke night at Rick's Bar Downstairs Stage in Key West. Known for his dynamic energy and engaging presence, Jason turns…
Free
Rolando Rojas at Sloppy Joe’s Bar
Experience the electrifying presence of Rolando Rojas at Sloppy Joe's Bar. Known as Key West's premier wedding entertainer, Rolando dazzles audiences with his exceptional guitar…
Free
Wynn Tayor ~ Rick’s Bar Downstairs Stage
Experience the captivating performance of Wynn Taylor at Rick's Bar Downstairs Stage. Located in the heart of Old Town Key West, this renowned musician brings…
Free
Tim Hollohan at Sloppy Joe’s Bar
Tim Hollohan, originally from Columbia, South Carolina, captivates audiences at Key West's historic Sloppy Joe's Bar with his engaging performances. A staple in the local…
Free
Tony Baltimore at Schooner Wharf Bar
Tony Baltimore captivates audiences at Schooner Wharf Bar, an iconic Key West venue known for its laid-back ambiance and stunning dockside views. With engaging performances…
Free
Tony Baltimore at Schooner Wharf Bar
Tony Baltimore captivates audiences at Schooner Wharf Bar, an iconic Key West venue known for its laid-back ambiance and stunning dockside views. With engaging performances…
Free
Jockey Jord at Sunset Pier
Experience the vibrant energy of Jockey Jord at Sunset Pier, where this talented musician captivates audiences with his live performances. Set against stunning Gulf of…
Free
Jessie Cotton Stone at The Bull & Whistle Bar
Experience the captivating performance of Jessie Cotton Stone at The Bull & Whistle Bar, a lively venue on Key West’s Duval Street. Known for his…
Free
Kari Wolf at Tiki House Key West
Experience the captivating performance of musician Kari Wolf at the vibrant Tiki House Key West. Renowned for her soulful melodies and dynamic stage presence, Kari…
Free
Joe the Show ~ Rick’s Bar Downstairs Stage
Experience the electrifying performance of Joe the Show at Rick's Bar Downstairs Stage in Old Town Key West. Known for his dynamic musical style and…
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
Snacks and Five at Sunset Pier
At Sunset Pier, enjoy an unforgettable evening with live entertainment from Snacks and Five, a dynamic musical group known for their vibrant performances. Set against…
Free
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Catch the dynamic duo Pete & Larry, better known as Sloppy 2nds, at the iconic Sloppy Joe's Bar. With their infectious humor and lively performances,…
Free
JOE THE SHOW ~ Durty Harry’s Stage
Experience an unforgettable evening with Joe The Show at Durty Harry's Stage, located within Rick's Entertainment Complex in Key West. As a captivating musician, Joe…
Free
Turner Harrison at Tiki House Key West
Enjoy an unforgettable evening with Turner Harrison at Tiki House Key West. Known for his charismatic stage presence and soulful melodies, Turner blends rock, folk,…
Free
Christopher Dean Band at Schooner Wharf Bar
Experience the electrifying performance of the Christopher Dean Band at Schooner Wharf Bar, Key West's iconic waterfront venue. Known for their captivating live shows, the…
Free
Christopher Dean Band at Schooner Wharf Bar
Experience the electrifying performance of the Christopher Dean Band at Schooner Wharf Bar, Key West's iconic waterfront venue. Known for their captivating live shows, the…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar, where the acclaimed magician dazzles with mind-blowing illusions and captivating performances. Nestled in Key…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar in Key West's Seaport. A master magician, Everhart captivates audiences with mesmerizing illusions and…
Free
DJ Marty ~ Red Garter Saloon Stage
DJ Marty electrifies the Red Garter Saloon Stage at Rick's Entertainment Complex in Key West, spinning vibrant beats that keep the dance floor alive. As…
Free
Colin Quinn at Key West Theater
Join comedian Colin Quinn at the Key West Theater for an unforgettable night of humor and wit. Known for his sharp, insightful comedy, Quinn effortlessly…
$
Elle Haley ~ Rick’s Bar Downstairs Stage
Experience the captivating talents of musician Elle Haley at Rick's Bar Downstairs Stage, located in the vibrant Rick's Entertainment Complex in Old Town Key West.…
Free
DJ Duke ~ Rick’s Bar Upstairs Stage
Experience an electrifying night with DJ Duke at Rick's Bar Upstairs Stage. Known for his dynamic mixes and infectious beats, DJ Duke transforms the largest…
Free
Andrew Gordon Band at The Bull & Whistle Bar
Experience the captivating sounds of the Andrew Gordon Band at The Bull & Whistle Bar in Key West. Andrew Gordon, a talented musician, brings his…
Free
DURTBAGS ~ Durty Harry’s Stage
Experience an electrifying night with The Durtbags, Key West's ultimate party rock band, performing live at Durty Harry’s Stage. Located in Rick's Entertainment Complex, their…
Free
Tequila Time Machine at General Horseplay
Tequila Time Machine electrifies General Horseplay in the heart of Old Town Key West with their lively performances. This talented band transforms the vibrant cocktail…
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,…
New Normal at Sloppy Joe’s Bar
Experience the electrifying performance of New Normal, a dynamic band from Bethlehem, PA, at Sloppy Joe's Bar. From 10:00 pm to 2:00 am, enjoy their…
Free
Mike Stack & D-Lew at Tiki House Key West
Join the dynamic duo, Mike Stack & D-Lew, at Tiki House Key West for an unforgettable musical experience. Their electrifying performances, marked by infectious energy…
Free
Karaoke w/ Jason ~ Rick’s Bar Downstairs Stage
Join Jason for an unforgettable karaoke night on the Downstairs Stage at Rick's Bar in Old Town Key West. Known for his dynamic hosting and…
Free