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.

Marathon

The Palm Deck

Rooftop cocktail lounge with ocean views, creative craft drinks, shareable plates, and live music in Marathon, Florida Keys.

Islamorada

Papa Joe's Waterfront

Papa Joe’s Waterfront – Waterfront dining & tiki-bar paradise in Islamorada with unbeatable sunset views.

Marathon

Dockside Boot Key Harbor

Dockside at Boot Key Harbor offers waterfront dining with fresh seafood, cocktails, and sweeping marina views in Marathon, FL.

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

Islamorada Brewery & Distillery

Discover award-winning craft beers, spirits, and vibrant island vibes in Islamorada!

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.

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

Marker 88

Marker 88 — iconic waterfront dining in Islamorada where sunset views, fresh seafood and island-crafted cocktails converge.

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.

Key West

Schooner Wharf Bar

Historic waterfront bar in Key West offering live music, fresh seafood, and island vibes.

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.

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

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.