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
The Lower Keys
Morning Joint
Morning Joint – A vibrant, pet-friendly café on Cudjoe Key serving farm-to-table coffee, made-to-order breakfast and lunch.
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
Green Parrot Bar
Green Parrot Bar is a legendary Key West dive bar near Duval Street known for live music, cold drinks, and a laid-back island vibe.
Marathon
The Palm Deck
Rooftop cocktail lounge with ocean views, creative craft drinks, shareable plates, and live music in Marathon, Florida Keys.
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 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.
Key Largo
Bayside Sunset Bar
Bayside Sunset Bar in Key Largo offers waterfront dining with spectacular sunset views, live music, and craft cocktails.
Islamorada
Marker 88
Marker 88 — iconic waterfront dining in Islamorada where sunset views, fresh seafood and island-crafted cocktails converge.
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
Hank's Hair of the Dog Saloon
Hank’s Hair of the Dog Saloon in Key West is a vibrant dog-friendly bar with live music, creative cocktails, and a renowned food truck on-site.
Marathon
The Brass Monkey
Long-running locals' bar featuring food, pool, darts, karaoke, and live music.
Marathon
Bongo's Botanical Beer Garden and Cafe
Bongo’s Botanical Beer Garden on Grassy Key offers a tropical oasis featuring over 20 craft beers on tap, garden‑fresh cocktails, and a vibrant food truck menu.
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.
Islamorada
Founders Park
45-acre recreation park in Islamorada with beach, pool, sports & playgrounds.
