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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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 Largo
Gilbert's Resort
Gilbert’s Resort & Marina is a laid-back waterfront resort in Key Largo, featuring waterfront rooms, a private beach, and the Keys’ largest tiki bar with live music and dining.
Key West
Key West Theater
The Key West Theater — performing arts & live events in Key West, where historic charm meets world-class entertainment.
Key West
The Backyard - Blue Flamingo
The Backyard Blue Flamingo in Key West serves up island-inspired eats, refreshing cocktails, and a relaxed, tropical backyard vibe.
Key West
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.
Islamorada
Papa Joe's Waterfront
Papa Joe’s Waterfront – Waterfront dining & tiki-bar paradise in Islamorada with unbeatable sunset views.
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.
Key West
La Concha Key West, Autograph Collection
Discover a historic Key West icon blending vintage flair with modern luxury.
Meetings Max
200
Total Space
1300 sq ft
Largest Room
600 sq ft
Key Largo
Skippers Dockside
Skipper’s Dockside — oceanfront seafood & comfort fare at Mile Marker 100 in Key Largo, where marina‑side views, live music and classic cocktails set the scene.
Key West
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.
Weddings Max
100
Meetings Max
70
Total Space
655 sq ft
Largest Room
655 sq ft
Key Largo
Snappers Oceanfront Restaurant & Bar
Snappers Oceanfront Restaurant & Bar in Key Largo serves vibrant waterfront dining with a casual Tiki Bar, live music, dockside seating, boat dockage, and a “Keysy” island vibe.
Marathon
The Brass Monkey
Long-running locals' bar featuring food, pool, darts, karaoke, and live music.
Key West
Rams Head Southernmost
Rams Head Southernmost — vibrant island dining & live-music bar in Key West, where craft beer, bold flavors and courtyard vibes meet.
Islamorada
Florida Keys Brewing Co.
Florida Keys Brewing Co. is the Upper Keys’ first microbrewery, serving award-winning craft beers in a vibrant beer garden and taproom located in Islamorada’s Morada Way Arts District—perfect for beer lovers and locals alike. Also offers a vacation rental.
Key West
Hard Rock Café
Hard Rock Cafe Key West on Duval Street blends American comfort food with rock-and-roll memorabilia and island energy.
