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.

Filters
Keys Season Deals
Destination
Category
Amenities
Key Largo

Pilot House Restaurant & Marina

Full-service marina & waterfront dining in the heart of Key Largo

The Lower Keys

Mangrove Mama's

Mangrove Mama’s — beloved seafood & steakhouse in Sugarloaf Key where Island-style flavors meet a laid-back Florida Keys vibe.

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.

Key West

Sunset Pier

Ocean Key Legacy Resort & Bar — iconic Key West destination featuring the famed Sunset Pier with cocktails, live music & nightly views.

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.

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

Snook's Bayside Restaurant & Grand Tiki

Snook’s Bayside Restaurant & Grand Tiki Bar offers waterfront dining with fresh seafood, tropical drinks, and magical sunset views on Key Largo.

Marathon

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort offers luxury oceanfront rooms and suites, five pools, a full-service spa & multiple dining options—all set on over a mile of private beachfront

Weddings Max
150
Meetings Max
300
Total Space
20000 sq ft
Largest Room
4000 sq ft

Islamorada

Tiki Bar at Three Waters Resort & Marina

The Tiki Bar at Three Waters Resort in Islamorada offers tropical cocktails, fresh bites, and stunning oceanfront views in a true island paradise.

Key Largo

Gilbert's Resort & Marina

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.

Weddings Max
1000

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

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 West

Celtic Conch Public House

Celtic Conch Public House is Key West’s authentic Irish pub, combining classic pub fare, over 40 Irish whiskeys, live music, and a rooftop lounge.

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