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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Islamorada
Crooked Palm Cabana
Crooked Palm Cabana is a cocktail lounge at Crooked Palm Distillery in Key West, serving handcrafted spirits, rum tastings, and tropical libations.
Key West
Sebago Watersports
Top-rated Key West watersports & sailing tours — snorkeling, sunset sails, parasailing & more.
Key West
Keys Caribbean Resorts
Explore KeysCaribbean: Expert hotel management and luxury vacation rentals.
Key Largo
Bayside Grille
Bayside Grille in Key Largo is a waterfront restaurant delivering vibrant Key-Caribbean cuisine, sunset views, and live music.
Islamorada
Dive Bar on the Bay
Dive Bar on the Bay in Tavernier is a waterfront bar and grill serving cold drinks, casual bites, and island views in a laid-back setting.
Marathon
Sparky's Landing - Fish n Cocktails
Sparky’s Landing in Marathon serves fresh seafood, island-inspired dishes, and tropical cocktails with stunning waterfront views.
Islamorada
Lorelei Restaurant & Cabana Bar
Waterfront dining with live music, stunning sunsets, and fresh seafood in Islamorada.
Key West
Sloppy Joe's Bar
A legendary Key West bar & live-music venue—Sloppy Joe’s offers tropical nightlife, cocktails, and island vibes since 1933.
Key West
Captain Tony's Saloon
Captain Tony’s Saloon is a historic Key West dive bar famous for its colorful past, live music, and legendary visitors like Ernest Hemingway and Jimmy Buffett.
Key West
Mangoes Restaurant
Mangoes — Caribbean-inspired dining on Duval Street in Key West, where fresh seafood and live music meet tropical island vibes.
Islamorada
Papa Joe's Waterfront
Papa Joe’s Waterfront – Waterfront dining & tiki-bar paradise in Islamorada with unbeatable sunset views.
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
The Rhum House
The Rhum House offers handcrafted cocktails, Caribbean-inspired dishes, and live music in a lively island atmosphere. Perfect for enjoying sunsets and tropical vibes.
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.
