Key West Live Music Events

The Greeen House Presents: Party In The Park with Just a Few Friends

Truman Waterfront Park 31 Aug 2025

Nautical Wheelers, a Tribute to Jimmy Buffett with Roger Bartlett

Sunset Pier, Key West, FL 33040, United States 30 Aug 2025

Mac McAnally in Key West

Key West Theater 5 Dec 2025

Second Line Memorial Walking Parade

100 Duval St, Key West, FL 33040-6506, United States 31 Aug 2025

Cheese Burger Beach Battle and Tribute Concert by Landshark

Southernmost Beach Resort 29 Aug 2025

A Sailor's Sun Sunset Cruise

Sunset Watersports 29 Aug 2025

Buffett Through The Years

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

Mac McAnally in Key West

Key West Theater 6 Dec 2025

Bubba's Official After Party

The Key West Empourium 31 Aug 2025

Clay Walker @ Country Music Cruise in Key West

Country Music Cruise 29 Oct 2025

Back to the Island Beach Party

801 Duval St, Key West, FL 33040-7405, United States 30 Aug 2025

Mac McAnally in Key West

Key West Theater 4 Dec 2025

Joe the Show & His Wheel of Musical Destiny at Mary Ellen's!

420 Appelrouth Lane, Key West, FL, United States, Florida 33040 15 Aug 2025

Outdoor Movie: Tales From Margaritavision

Southernmost Pint Brewpub 29 Aug 2025

Tay Tay Tuesday - In Your Wildest Dreams

Sunset Pier ~ Key West 21 Oct 2025

Puddles Pity Party at Key West Theater

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

Jesse Rice - SOLD OUT

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

Just a Few Friends Pool Party @ the Marker

The Marker Key West Resort 31 Aug 2025

Happy Hour at the Chart Room

Chart Room 29 Aug 2025

Just a Few Friends Celebration, Key West

Key West 29 Aug 2025

August's Community Swim Night!!

1319 Duval Street, Key West, FL, United States, Florida 33040 16 Aug 2025

The Brit Pack: The Ultimate British Music Experience

Key West Theater 17 Jan 2026

Artisan Market @ the Party in the Park - Just a Few Friends

Truman Waterfront Park 31 Aug 2025

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

Sunset Pier ~ Key West 11 Oct 2025

🎶Blue Heaven🎶

Blue Heaven 30 Aug 2025

Mac McAnally at Key West Theater

Key West Theater 5 Dec 2025

Dub Pool Party at The Marker Key West

The Marker Key West 15 Aug 2025

Rum Fest: Cliff Cody & Sharese

Key West Theater 13 Aug 2025

September's Community Swim Night

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

DINNER & A SHOW - TONY BALTIMORE makes you dinner!

Key West Theater 26 Nov 2025

Zach Deputy

0 Duval Street, Key West, FL, United States, Florida 33040 11 Aug 2025

"Gypsies In The Palace" Buffett Tribute Band

Hog's Breath Saloon 29 Aug 2025

Dave Matthews Tribute Band - BIG Stage / FREE Show

0 Duval Street, Key West, FL, United States, Florida 33040 17 Oct 2025

October's Community Swim

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

Buffett Through The Years - Tribute to Jimmy Buffett

Key West Theater 30 Oct 2025

25th Annual Living Art Expo

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

Best of Key West Jazz Concert Series!

803 Emma St, Key West, FL, United States, Florida 33040 27 Aug 2025

Tap Takeover Pool Party at Winslow’s Bungalows Thursday, August 28th, 2-5pm

725 Truman Ave, Key West, FL 33040-6423, United States 28 Aug 2025

Shoreline Sessions Reggae Beach Festival

1319 Duval Street, Key West, FL, United States, Florida 33040 1 Nov 2025

Dead Zep at Key West Theater

Key West Theater 1 Nov 2025

Will Kimbrough

Key West Theater 30 Oct 2025

JESS & JILL - AT THE ALAMO

4 Charles St, Key West, FL, United States, Florida 33040 19 Aug 2025

Femmes of Rock in Key West, FL!

Key West Theater 10 Dec 2025

Phil Collins Experience at Key West Theater

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

Tom Sandoval & The Most Extras

Key West Theater 9 Oct 2025

Will Kimbrough Dockside Lounge

0 Duval Street, Key West, FL, United States, Florida 33040 1 Sep 2025

On Our Way To Paddy's Day Weekend Celebration!

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

Official Rum Fest Event! Papa's Pilar Rum Cocktail Contest | Pool Party | Music by K Dub-Ya

200 William St, Key West, FL, United States, Florida 33040 15 Aug 2025

TuTu Tuesday 2025 - Tuesday Night Fever & Our Robot Friends

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

Crystal Gayle at Key West Theater

Key West Theater 22 Nov 2025

Sloppy Joe's 46th Annual Toga Party

Sloppy Joe's 23 Oct 2025

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

The Alamo Key West 21 Nov 2025

Key West Halloween Drag Brunch Royale

Mangoes Restaurant 19 Oct 2025

Crystal Gayle

Key West Theater 21 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

Femmes of Rock

Key West Theater 10 Dec 2025

Parking Diva Royale - Key West

Diva Royale Drag Queen Show - Key West 30 May 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

Kaitlin Butts in Key West

Truman Waterfront Park Amphitheater 29 Jan 2026

Kaitlin Butts in Key West

Truman Waterfront Park Amphitheater 30 Jan 2026

Anthony Rodia at Key West Theater

Key West Theater 11 Dec 2025

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

Jesse Rice in Key West

Key West Theater 16 Aug 2025

Jesse Rice in Key West

Key West Theater 15 Aug 2025

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

AG at Sloppy Joes Key West Aug 27-Sept 2!

Sloppy Joe's Bar 27 Aug 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