Key West Live Music Events

5th Annual Party Like A Rockstar Party

The Key West Empourium 21 Oct 2026

A Green Parrot Beatle Tribute

The Green Parrot 19 Oct 2026

VIVA'S GRAND FINALE - FANTASY FEST PARADE VIEWING & DINNER PARTY

Viva Argentinian Steakhouse 24 Oct 2026

Buffett Through the Years

Key West Theater 30 Oct 2026

Sins & Sequins - An Official Fantasy Fest Event

Blue Flamingo Resort Key West 21 Oct 2026

Sloppy Joe's Comic Book Caper-ers Party

Sloppy Joe's Key West 19 Oct 2026

Candlelight: Coldplay vs. Imagine Dragons

Key West Theater 13 Nov 2026

Irish Kevin's Annual 80's Party

211 Duval St, Key West, FL, United States, Florida 33040 22 Oct 2026

KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Half Shell Raw Bar 14 Nov 2026

2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"!

Sebago Watersports 31 Oct 2026

Candlelight: The Best of Hans Zimmer

Key West Theater 13 Nov 2026

FUNKY GRATEFUL DEAD GET DOWN PARTY (6-piece band) & 4 DJ's AFTER PARTY

Viva Argentinian Steakhouse 23 Oct 2026

Swayzees Music Icons Pool Party at Shores Pool

Southernmost Beach Resort 21 Oct 2026

Tay-Tay Tuesday - Life of a Showgirl

0 Duval Street, Key West, FL, United States, Florida 33040 20 Oct 2026

Masquerade Monday Wine Dinner Presented by Bogle Wines

A&B Lobster House 19 Oct 2026

Les Greene & The Swayzees Musical Icons Pool Party Take 2 At The Marker Resort

The Marker Key West Resort 22 Oct 2026

2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise"

Sebago Watersports 30 Oct 2026

Wharfstock at the Schooner Wharf Bar

Schooner Wharf Bar 21 Oct 2026

IAN MAKSIN in KEY WEST: "SONGS of LOVE & PEACE" 2026 Concert Tour

Congregation B'nai Zion 11 Nov 2026

Candlelight: Vivaldi's Four Seasons

Key West Theater 11 Dec 2026

Candlelight: Tribute to Fleetwood Mac

Key West Theater 11 Dec 2026

Fantasy Fest Les Greene & the Swazees The Marker Key West Harbor Resort on October 22

The Marker Key West Harbor Resort 22 Oct 2026

Mac McAnally in Key West

Key West Theater 18 Dec 2026

Tim Palmieri & Friends at The Green Parrot

The Green Parrot 11 Dec 2026

The Jayhawks

Key West Theater 25 Jan 2027

Classic Seger: Bob Seger's Greatest Hits Live (9PM)

Key West Theater 23 Jan 2027

Sunny Jim, Florida Days

Key West Theater 30 Oct 2026

Old Crow Medicine Show in Key West

Truman Waterfront Park Amphitheater 26 Jan 2027

Justin Angelo at Sunset Tiki

Sunset Tiki 18 Oct 2026

The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers

Key West Theater 12 Dec 2026

December Duo Holiday Concert: Irie Monte and Crispin Campbell

533 Eaton St, Key West, FL, United States, Florida 33040 12 Dec 2026

Candlelight: Christmas Classics

Key West Theater 26 Dec 2026

Sloppy Joe's Slumber Party

Sloppy Joe's Key West 21 Oct 2026

Mac McAnally at Key West Theater

Key West Theater 18 Dec 2026

Thunder from Down Under : Unleashed World Tour

Key West Theater 28 Mar 2027

Rob Benton Concert and Pool Party at The Marker Key West Harbor Resort on November 1

The Marker Key West Harbor Resort 1 Nov 2026

Fabulous Spectrelles

Kaya Island Eats 9 Oct 2026

Put-in-Bay Days in Key West 2027

Key West, Florida 10 Feb 2027

A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg, Reese Dailey & Special Guests

Key West Theatre 13 Feb 2027

The Phil Collins Experience

Key West Theater 20 Jan 2027

The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band

Key West Theater 1 Jan 2027

Double Duran "The Ultimate Duran Duran Experience"

Key West Theater 18 Jan 2027

Kaitlin Butts in Key West

Truman Waterfront Park Amphitheater 26 Jan 2027

November's Walk On White

1110 White Street, Key West, FL, United States, Florida 33040 19 Nov 2026

Peter Mayer: A Stars & Promises Christmas "This Town"

Key West Theater 29 Nov 2026

Keller Williams Trio at Key West Theater

Key West Theater 2 Jan 2027

AG at Fantasy Week at Sloppy Joes!

Sloppy Joe's Bar 18 Oct 2026

3rd Annual Moose March

Key West Moose Lodge 1760 7 Mar 2027

Thanksgiving at Four Marlins

1435 Simonton St, Key West, FL, US 33040 26 Nov 2026

Elton Dan & The Rocket Band

Key West Theater 13 Mar 2027

Kash'd Out

Key West Theater 16 Jan 2027

Sunny Jim, “The Cayman Years” in Songs and Stories

Key West Theater 29 Oct 2026

December's Walk On White

1110 White Street, Key West, FL, United States, Florida 33040 17 Dec 2026

CANN PRESENTS: YACHT ROCK REVUE - PRIMETIME

Coffee Butler Amphitheater 20 Jan 2027

MiniKiss

Key West Theater 14 Mar 2027

November's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 14 Nov 2026

Rumours ATL: A Fleetwood Mac Tribute

Key West Theater 20 Mar 2027

DMTB: The Dave Matthews Tribute Band- Burnin’ One Tour

Key West Theater 24 Feb 2027

February's Walk On White

1110 White Street, Key West, FL, United States, Florida 33040 18 Feb 2027

December's Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 12 Dec 2026

Fantasy Fest Channel 3 Reggae Rehab The Marker Key West Harbor Resort on October 25

The Marker Key West Harbor Resort 25 Oct 2026

Fantasy Fest 5K Run/Walk & Run Like a Rockstar 1 Mile

203 DUVAL ST , KEY WEST, FL, 33040, US, 33040 19 Oct 2026