Key West Live Music Events

Mac McAnally in Key West

Key West Theater 5 Dec 2025

Buffett Through The Years

512 Eaton St, Key West, FL, United States, Florida 33040 31 Oct 2025

Clay Walker @ Country Music Cruise in Key West

Country Music Cruise 29 Oct 2025

Mac McAnally in Key West

Key West Theater 6 Dec 2025

September's Community Swim Night

1319 Duval Street, Key West, FL, United States, Florida 33040 20 Sep 2025

Tay Tay Tuesday - In Your Wildest Dreams

Sunset Pier ~ Key West 21 Oct 2025

Dead Zep at Key West Theater

Key West Theater 1 Nov 2025

Mac McAnally in Key West

Key West Theater 4 Dec 2025

Mike Stack and Friends on the BIG stage at the Sunset Pier

Sunset Pier ~ Key West 11 Oct 2025

Puddles Pity Party at Key West Theater

512 Eaton St, Key West, FL, United States, Florida 33040 28 Sep 2025

The Brit Pack: The Ultimate British Music Experience

Key West Theater 17 Jan 2026

Sharese Nicole LIVE at Sunset Lounge Bar and Grill

Sunset Lounge Sigsbee 12 Sep 2025

Mac McAnally at Key West Theater

Key West Theater 5 Dec 2025

Good Trees River Band at The Green Parrot

Green Parrot Key West 12 Sep 2025

Scott Kirby- 35 Years of Songs & Stories

Key West Theater 13 Feb 2026

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

The Alamo Key West 21 Nov 2025

Tom Sandoval & The Most Extras

Key West Theater 9 Oct 2025

Jerry Kramer LIVE at Sunset Lounge Bar and Grill

Sunset Lounge Sigsbee 19 Sep 2025

October's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 11 Oct 2025

25th Annual Living Art Expo

0 Duval Street, Key West, FL, United States, Florida 33040 24 Oct 2025

TuTu Tuesday 2025 - Tuesday Night Fever & Our Robot Friends

423 Caroline street, Key West, FL, United States, Florida 33040 21 Oct 2025

Macy Gray-On How Life Is 25th Anniversary Tour

Key West Theater 24 Oct 2025

Cartel Autotronics & Petersons Harley South Beachside Bike & Slingshot Show

Casa Marina Key West, Curio Collection by Hilton 20 Sep 2025

Sloppy Joe's Comic Book Cape-ers Party

Sloppy Joe's Bar 20 Oct 2025

November's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 15 Nov 2025

Oktoberfest

Sunset Lounge Sigsbee 26 Sep 2025

Scott Kirby- 35 Years of Songs & Stories

Key West Theater 12 Feb 2026

Scott Kirby- 35 Years of Songs & Stories

Key West Theater 26 Feb 2026

On Our Way To Paddy's Day Weekend Celebration!

528 Front Street, Key West, FL, United States, Florida 33040 9 Oct 2025

The Garcia Project: Performing classic Jerry Garcia Band Set Lists from 1976-1995

512 Eaton St, Key West, FL, United States, Florida 33040 15 Nov 2025

DINNER & A SHOW - TONY BALTIMORE makes you dinner!

Key West Theater 26 Nov 2025

Crystal Gayle at Key West Theater

Key West Theater 22 Nov 2025

Key West Halloween Drag Brunch Royale

Mangoes Restaurant 19 Oct 2025

Good Trees River Band at General Horseplay

General Horseplay 9 Sep 2025

Phil Collins Experience at Key West Theater

512 Eaton St, Key West, FL, United States, Florida 33040 26 Jan 2026

Changes In Latitude at Key West Theater

512 Eaton St, Key West, FL, United States, Florida 33040 3 Mar 2026

Sloppy Joe's 46th Annual Toga Party

Sloppy Joe's 23 Oct 2025

Crystal Gayle

Key West Theater 21 Nov 2025

A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg and Reese Dailey

Key West Theatre 14 Feb 2026

Will Kimbrough

Key West Theater 30 Oct 2025

Golden Girls: The Tribute Show - A Drag Parody

Key West Theater 16 Nov 2025

Los Lobos at Key West Theater

Key West Theater 13 Jan 2026

Rumours ATL: A Fleetwood Mac Tribute

Key West Theater 21 Jan 2026

Savannah Brady @ Wellen Park

Wellen Park Florida 23 Oct 2025

DMTB: The Dave Matthews Tribute Band

Key West Theater 25 Feb 2026

Femmes of Rock in Key West, FL!

Key West Theater 10 Dec 2025

Savannah Brady @ Wellen Park

Wellen Park Florida 6 Nov 2025

Ann Hampton Callaway - Finding Beauty: Inspired Classics and Originals

Tennessee Williams Theatre 17 Nov 2025

Elton Dan and the Rocket Band at Key West Theater

Key West Theater 12 Nov 2025

Clay Walker in Key West

Country Cruising 29 Oct 2025

BeachFront Radio and Trop Rock'N Duval presents The Margarita Brothers @ Key West Theater

Key West Theater, 512 Eaton St. Key West, FL 33040 30 Oct 2025

Kaitlin Butts in Key West

Truman Waterfront Park Amphitheater 29 Jan 2026

Kaitlin Butts in Key West

Truman Waterfront Park Amphitheater 30 Jan 2026

Put-in-Bay Days in Key West 2026

Key West, Florida 11 Feb 2026

Elton Dan and the Rocket Band

Key West Theater 11 Nov 2025

Tanner Usrey in Key West

Truman Waterfront Park Amphitheater 27 Jan 2026

Randy Rogers Band in Key West

Truman Waterfront Park Amphitheater 27 Jan 2026

Sugar Ray in Key West

Key west cruise port 28 Jan 2026

Uncle Lucius in Key West

Truman Waterfront Park Amphitheater 27 Jan 2026

Key West trip with the Barefoot Bay Travelers Club

Fairfield Inn & Suites by Marriott Key West at The Keys Collection 15 Oct 2025

RockHouse LIVE at Sloppy Joe's, Key West, FL!

Sloppy Joes, Key West 8 Oct 2025

Sugar Ray @ Key west cruise port in Key West

Key west cruise port 28 Jan 2026