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
Sunday, December 14, 2025
Alfonse at Two Friends Patio Restaurant & Bar
Dec. 14, 2025 - 8:30 a.m. - 11:30 a.m.
Two Friends Patio Restaurant & Bar - 512 Front St, Key West, FL 33040
Chris Thomas at Sloppy Joe's Bar
Dec. 14, 2025 - 10 a.m.
Sloppy Joe's Bar - 201 Duval St, Key West, FL 33040
Bradd Shadduck at Irish Kevin's
Dec. 14, 2025 - 11 a.m. - 1:30 p.m.
Irish Kevin's - 211 Duval St, Key West, FL 33040
NFL Sunday At Boondocks at Boondocks Grille
Dec. 14, 2025 - 11 a.m. - 10 p.m.
Boondocks Grille - 27205 Overseas Hwy, Ramrod Key, FL 33042
John LaMere at Sloppy Joe's Bar
Dec. 14, 2025 - noon
Sloppy Joe's Bar - 201 Duval St, Key West, FL 33040
Cayman & Company at 1:00 & 3:00 at Green Parrot Bar
Dec. 14, 2025 - 1 p.m.
Green Parrot Bar - 601 Whitehead St, Key West, FL 33040
Jeff Harris at Irish Kevin's
Dec. 14, 2025 - 1:30 p.m. - 6 p.m.
Irish Kevin's - 211 Duval St, Key West, FL 33040
Jannik at Tipsy Rooster Liquor Store and Bar
Dec. 14, 2025 - 2 p.m. - 5 p.m.
Tipsy Rooster Liquor Store and Bar - 1325 Simonton St, Key West, FL 33040
TEA DANCE! at La Te Da
Dec. 14, 2025 - 4 p.m. - 6:30 p.m.
La Te Da - 1125 Duval St, Key West, FL 33040
Robert Albury Band at Sunset Pier
Dec. 14, 2025 - 5 p.m. - 7 p.m.
Sunset Pier - 0 Duval St, Key West, FL 33040
Jerome & Wynn at Alamo Key West
Dec. 14, 2025 - 5:30 p.m. - 8:30 p.m.
Alamo Key West - 4 Charles St, Key West, FL 33040
Mojito at Sloppy Joe's Bar
Dec. 14, 2025 - 5:30 p.m.
Sloppy Joe's Bar - 201 Duval St, Key West, FL 33040