Live Entertainment
Nightlife in Key West
Discover live music in Key West, the ultimate destination for unforgettable entertainment and nightlife! Our Key West live music calendar showcases today's hottest performances at vibrant bars and outdoor venues both on and off Duval Street. Experience island rhythms at all hours—sing along, dance under the stars, or unwind with your favorite local bands. Check out the complete Key West music schedule and immerse yourself in the lively atmosphere of this renowned live entertainment hotspot. Don’t miss tonight’s shows and events; join the party and feel the beat of paradise in Key West! View Entertainment Schedule by Venue
Thursday, August 13, 2026
Karaoke w/ Jason at Rick's Bar Key West
Aug. 13, 2026 - 11:59 p.m. - 4 a.m.
Rick's Bar Key West - 202-208 Duval Street, Key West, FL 33040
Friday, August 14, 2026
Rolando Rojas at Sloppy Joe's Bar
Aug. 14, 2026 - 10 a.m.
Sloppy Joe's Bar - 201 Duval St, Key West, FL 33040
Jeff Harris at Irish Kevin's
Aug. 14, 2026 - 11 a.m. - 2:30 p.m.
Irish Kevin's - 211 Duval St, Key West, FL 33040
Elle Haley at Hog's Breath Saloon
Aug. 14, 2026 - noon - 4 p.m.
Hog's Breath Saloon - 400 Front St, Key West, FL 33040
Elle Haley, a 25-year-old musician from Westfield, NJ, has been captivated by Key West since childhood. Fueled by a passion for music, she dedicated a year after high school to honing her craftbuilding a steel-string acoustic guitar by hand in England, mastering songwriting in Colorado, and immersing herself in Key Wests vibrant music scene. Now, three years into her flourishing career, Elle performs at renowned venues and embraces the culture and adventures of Key West. Experience Elle Haley live or book her for your next private event and let her soulful melodies make your occasion unforgettable!
Jonathan Williams at Pier House Resort & Spa
Aug. 14, 2026 - noon - 3 p.m.
Pier House Resort & Spa - One Duval St, Key West, FL 33040
Philadelphia native Jonathan Williams, a versatile musician with nearly 15 years of experience, excels in delivering iconic hits spanning five decades. Based in Key West, he has performed over 400 shows at his peak, enchanting audiences at top venues, weddings, and private events across the Florida Keys and South Florida.
Tim Hollohan at Sloppy Joe's Bar
Aug. 14, 2026 - noon
Sloppy Joe's Bar - 201 Duval St, Key West, FL 33040
Tony Baltimore at Schooner Wharf Bar & Grill
Aug. 14, 2026 - noon - 5 p.m.
Schooner Wharf Bar & Grill - 202 William St, Key West, FL 33040
Tony Baltimore, a dynamic singer/songwriter and multi-instrumentalist raised in Maryland, blends alternative roots-rock with influences from New Orleans, Brit-pop, and gospel. A Key West icon, Tonys musical journey began with drums at age four, evolving into a vibrant career shaped by legends like The Beatles and Queen. After earning his MFA in poetry, he found creative inspiration in Key Wests unique music scene, releasing acclaimed albums like Define the Blur and Hear Me In. His latest work, Lets All Go Insane, showcases hook-driven, genre-bending tracks. Known for electrifying performances, Tony continues to captivate audiences with heartfelt storytelling and bold creativity.
Wynn Tayor at Rick's Bar Key West
Aug. 14, 2026 - noon - 4 p.m.
Rick's Bar Key West - 202-208 Duval Street, Key West, FL 33040
A Pirate Looks Back: Jimmy Buffett Tribute Show at Comedy Key West
Aug. 14, 2026 - 12:30 p.m.
Comedy Key West - 218 Whitehead St, Unit 5, Key West, FL 33040
Marcy Kaelyn at Hemingway Social Club
Aug. 14, 2026 - 1:30 p.m. - 4:30 p.m.
Hemingway Social Club - 201 Simonton St, Key West, FL 33040
Shastina Chiles at Hank's Hair of the Dog Saloon
Aug. 14, 2026 - 2 p.m. - 4 p.m.
Hank's Hair of the Dog Saloon - 409 Caroline St, Key West, FL 33040
Shastina Chiles, a gifted songwriter and performer, captivates audiences with her distinctive blend of Pop and R&B. Based in Key West, she delivers powerful, guitar-driven performances at top venues and live streams for her growing fan base nationwide. Shastina has shared stages with icons like Phil Vassar, Molly Hatchet, and Jimmy Buffett, offering both popular covers and soulful original songs.
James Kelly at Irish Kevin's
Aug. 14, 2026 - 2:30 p.m. - 6:30 p.m.
Irish Kevin's - 211 Duval St, Key West, FL 33040