Live music in Key West, FL

This poolside celebration brings together Four Flamingos for a Key West and Orlando collaboration that highlights coastal flavors. Guests and locals can enter at no cost, with live music and tropical vibes throughout. Chef-crafted lobster dishes will be available to purchase from both locations, including a Tropical Lobster Salad from Four Flamingos Key West for $15 and a Lobster Roll from Four Flamingos Orlando for $15.

Celebrated as Key West's longest running musical revue, The Fabulous Spectrelles have entertained audiences for more than 43 years. This lively production honors the Motown and doo wop classics of the 1950s and 60s with vibrant energy and rich harmonies. The group appears in residence at The Key West EmPOURium, with performances hosted in the Karaoke Lounge.

Karaoke Night takes over Boardwalk Bar & Grill in Big Pine Key. Step up to the microphone, belt out favorite songs, and enjoy drink specials. It is a lively choice for a memorable evening with friends.

At the Shores Pool, a community swim offers live music, complimentary swag, and an appearance by Mermaid Dorian. It is part of a monthly series that is open to the public.

Catch The Quickening for a special soundcheck set at Green Parrot Bar. The band will play a single 90-minute performance, with music described as funkified and feel-good, leaning into the vibrant energy of New Orleans.

Enjoy live music with Aaron Hudgins at Rick's Bar Key West. The show runs from 8:00 PM until 11:59 PM, and it takes place on the downstairs stage at Rick's Bar.

Nick Norman appears at First Flight.

Enjoy a live music performance by Charles Miller at Rick's Bar Key West. The show runs in the evening with music from 7:00 PM to 11:00 PM, hosted on the downstairs stage.

Joe the Show is playing live on the downstairs stage at Rick's Bar in Key West. The music runs from 7:00 PM to 11:00 PM on Tuesday evening.

Key West RumFest is a lively island celebration focused on rum tastings, handcrafted tropical cocktails, and great entertainment. Expect live music, plenty of Key West charm, and a laid-back weekend atmosphere filled with fun, flavor, and coastal energy.

Catch DJ Todd for live music at Rick's Bar in Key West. The event runs late into the night, so plan for an extended set and a fun night out along Duval Street.

Catch live performances with Joe the Show at Rick's Bar Key West. The show runs on Thursday evening from 7:00 PM to 11:00 PM at the downstairs stage.

Relive the early 2000s at 22&Co with Joe during a Thursday celebration that channels the spirit of 2001. The throwback fun continues on Thursdays throughout 2026.