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.
Filters
Islamorada
Oceanview Inn & Sports Club
The Ocean View Inn & Sports Pub in Islamorada offers comfortable accommodations with a tropical flair, an outdoor pool, and a lively pub serving classic American fare and late-night bites.
Marathon
Barnacle Barney's Tiki Bar and Grill
Barnacle Barney’s Tiki Bar & Grill in Marathon offers waterfront dining, tropical drinks, and live music in a laid-back Keys setting.
Key West
Irish Kevin's
Irish Kevin’s in Key West is a legendary Duval Street bar known for its live music, hilarious entertainment, and lively crowd.
The Lower Keys
Boondocks Grille and Draft House
Boondocks Grille & Draft House is a lively waterfront restaurant and tiki bar in Ramrod Key, offering fresh seafood, burgers, live music, and the only 18-hole mini-golf course in the Florida Keys.
Islamorada
Islander Resort
Escape to Islander Resort: vibrant Florida Keys stays, beachside dining, and endless adventures!
Meetings Max
1000
Total Space
19000 sq ft
Largest Room
2760 sq ft
Marathon
Lighthouse Kitchen + Bar
Lighthouse Kitchen + Bar – waterfront seafood restaurant in Marathon, where fresh local flavors and sunset views shine.
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.
Key West
Hog's Breath Saloon
Hog’s Breath Saloon in Key West is a legendary bar and grill serving cold drinks, live music, and laid-back island vibes just steps from Duval Street.
Key West
Sunset Pier
Ocean Key Legacy Resort & Bar — iconic Key West destination featuring the famed Sunset Pier with cocktails, live music & nightly views.
Marathon
Havana Jack's Oceanside Restaurant and Bar
Experience vibrant American Caribbean flavors and lively atmosphere at Havana Jack's Oceanside!
Key West
22&Co
22&Co is a whimsical cocktail bar in Key West serving fresh, glitter-infused drinks with fun bartenders, tutus, and unicorn flair.
Islamorada
Marker 88
Marker 88 — iconic waterfront dining in Islamorada where sunset views, fresh seafood and island-crafted cocktails converge.
Key West
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.
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.
