Sunset outdoor party with people dancing near a waterfront stage.

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

The SandBAR at Whale Harbor

Whale Harbor Sandbar offers waterfront dining and tropical drinks in a vibrant Key West setting. Perfect for enjoying fresh seafood and stunning sunset views.

Key Largo

Caribbean Club

Historic Florida Bay bar with stunning sunsets, live bands, karaoke nights, and signature rum punches — a beloved local hangout in Key Largo, FL.

Key Largo

Bayside Sunset Bar

Bayside Sunset Bar in Key Largo offers waterfront dining with spectacular sunset views, live music, and craft cocktails.

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.

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.

Marathon

Lighthouse Kitchen + Bar

Lighthouse Kitchen + Bar – waterfront seafood restaurant in Marathon, where fresh local flavors and sunset views shine.

Key West

The Gardens Hotel & Cottages d'vine Wine Gallery

The Gardens Hotel is a boutique hotel in Key West, offering luxurious accommodations, lush tropical gardens, and a serene atmosphere, just steps from Duval Street.

Key West

Mangoes Restaurant

Mangoes — Caribbean-inspired dining on Duval Street in Key West, where fresh seafood and live music meet tropical island vibes.

Key West

Flama Cabana

Flama Cabana is a vibrant waterfront cocktail lounge in Key West offering Cuban-inspired tapas, rum-forward cocktails, live music, and ocean views at Havana Cabana resort.

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.

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

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

The Hilton Key West Resort & Marina

The Hilton Key West Resort & Marina is a luxury waterfront resort on Stock Island, featuring six heated saltwater pools, a 165-slip marina, an on-site restaurant, and complimentary shuttle service to Old Town Key West.

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.