Live Music
Music is part of the rhythm of life in The Florida Keys & Key West. From waterfront tiki bars and open-air patios to intimate lounges and lively stages, live music drifts through the islands nearly every night of the week. Local bands, touring acts, and talented solo performers keep the soundtrack going with everything from reggae and rock to jazz, country, and island-inspired favorites. Grab a drink, watch the sunset, and settle in. The next great song is probably starting somewhere nearby.
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General Horseplay
General Horseplay in Key West is a lively cocktail bar offering inventive drinks, gourmet snacks, and nightly entertainment in a cozy, retro-chic setting.
Havana Jack's Oceanside Restaurant and Bar
Experience vibrant American Caribbean flavors and lively atmosphere at Havana Jack's Oceanside!
Sunset Pier
Ocean Key Legacy Resort & Bar — iconic Key West destination featuring the famed Sunset Pier with cocktails, live music & nightly views.
The Saint Hotel
The Saint Hotel Key West, Autograph Collection, is an adults-only boutique hotel located at 417 Eaton Street in Old Town Key West.
El Meson De Pepe
El Meson de Pepe is an iconic Cuban restaurant in Key West, located on Mallory Square, offering authentic Cuban cuisine and tropical cocktails in a lively, festive atmosphere.
Morning Joint
Morning Joint – A vibrant, pet-friendly café on Cudjoe Key serving farm-to-table coffee, made-to-order breakfast and lunch.
The Marker Key West Harbor Resort
The Marker Key West Harbor Resort is a luxury hotel located in Old Town Key West, offering a blend of classic Florida Keys elegance and modern amenities.
Willie T's Restaurant and Bar
Willie T’s in Key West is a lively Duval Street bar and restaurant known for its tropical drinks, live music, and upbeat island atmosphere.
Southernmost Beach Resort
Southernmost Beach Resort & Guesthouses is an oceanfront Key West escape featuring multiple heated pools, beachfront dining, a full-service spa, and lush tropical gardens just steps from Duval Street.
Bayside Sunset Bar
Bayside Sunset Bar in Key Largo offers waterfront dining with spectacular sunset views, live music, and craft cocktails.
Bali Bar
Relax with creative tropical cocktails, live music, and laid-back island vibes at the Bali Bar inside The Key West Hotel on Duval Street, Key West, FL.
Pilot House Restaurant & Marina
Full-service marina & waterfront dining in the heart of Key Largo
Lorelei Restaurant & Cabana Bar
Waterfront dining with live music, stunning sunsets, and fresh seafood in Islamorada.
22&Co
22&Co is a whimsical cocktail bar in Key West serving fresh, glitter-infused drinks with fun bartenders, tutus, and unicorn flair.
Lighthouse Hotel
Historic charm meets vibrant Key West life steps from Hemingway House and the iconic lighthouse.