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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Marathon
The Rhum House
The Rhum House Key West offers handcrafted cocktails, Caribbean-inspired dishes, and live music in a lively island atmosphere. Perfect for enjoying sunsets and tropical vibes.
Marathon
The Palm Deck
Rooftop cocktail lounge with ocean views, creative craft drinks, shareable plates, and live music in Marathon, Florida Keys.
The Lower Keys
Morning Joint
Morning Joint – A vibrant, pet-friendly café on Cudjoe Key serving farm-to-table coffee, made-to-order breakfast and lunch.
Key West
Lighthouse Hotel
Historic charm meets vibrant Key West life steps from Hemingway House and the iconic lighthouse.
Weddings Max
60
Meetings Max
60
Key West
Keys Caribbean Resorts
Explore KeysCaribbean: Expert hotel management and luxury vacation rentals.
Marathon
Havana Jack's Oceanside Restaurant and Bar
Experience vibrant American Caribbean flavors and lively atmosphere at Havana Jack's Oceanside!
Key West
The Alamo Key West
The Alamo Key West is a laid-back local bar known for its friendly atmosphere, cold drinks, and classic island charm.
Key West
RockHouse Live Key West
Lively multi-level bar and entertainment spot on Duval Street with live bands, karaoke, DJs, food, drinks, and a rooftop deck in the heart of Key West nightlife.
Key West
Celtic Conch Public House
Celtic Conch Public House is Key West’s authentic Irish pub, combining classic pub fare, over 40 Irish whiskeys, live music, and a rooftop lounge.
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.
Key West
Hank's Hair of the Dog Saloon
Hank’s Hair of the Dog Saloon in Key West is a vibrant dog-friendly bar with live music, creative cocktails, and a renowned food truck on-site.
Key West
Sunset Pier
Ocean Key Legacy Resort & Bar — iconic Key West destination featuring the famed Sunset Pier with cocktails, live music & nightly views.
Key West
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.
The Lower Keys
Looe Key Reef Resort & Dive Center
Looe Key Reef Resort offers beachfront accommodations, daily scuba and snorkeling trips, a full-service dive shop, and a Tiki Bar with live entertainment in the Florida Keys.
