Key West Parties Events

Running of the Elves

Key West 20 Dec 2025

Custom House Holiday Concert & Bazaar

Key West Art & Historical Society 12 Dec 2025

Freedom Flotilla Festival

Key West, Floirda 19 Dec 2025

31st Annual Taste of Key West

Truman Waterfront, Key West, FL, United States, Florida 33040 23 Mar 2026

New Moon Drum Circle

The Greeen House 19 Dec 2025

"Island Snoop" on the Stoop Photos

The Greeen House 20 Dec 2025

17th Annual Rudolph APSMC 5K

Southernmost Beach Resort 13 Dec 2025

Red, lights and GrEEEn Holiday Golf Cart light Tour- The town is LIT!

The Greeen House 17 Dec 2025

Ugly Christmas Sweater Party

504 Angela St, Key West, FL, United States, Florida 33040 20 Dec 2025

Freedom Flotilla Festival

Key West 19 Dec 2025

Great Gatsby NYE 2026

First Flight Island Restaurant & Brewery 31 Dec 2025

Tim Palmieri & Friends at The Green Parrot

The Green Parrot 12 Dec 2025

Winter Party & Holiday Lights Trolley

May Sands Montessori School 12 Dec 2025

Q West: Comedy Escape 2026

Key West Theater 10 Apr 2026

Put-in-Bay Days in Key West 2026

Key West, Florida 11 Feb 2026

December' Community Swim

1319 Duval Street, Key West, FL, United States, Florida 33040 13 Dec 2025

Christmas on the Farm Open House

Monroe County Sheriff's Office Animal Farm 14 Dec 2025

Jesse Rice’s “Party At The Pier House” Show

Pier House Resort & Spa 7 Mar 2026

Cupid's Chase 5K Key West

Clarence S.Higgs Memorial Beach 14 Feb 2026

Mingle & Jingle - Holiday Cookie Crawl

The Shops at Mallory Square 12 Dec 2025

BoDeans: 40 Years of Love & Hope & Sex & Dreams... and Good Things

Key West Theater 29 Mar 2026

Tropical Luncheon & Garden Party

Key West Woman's Club 8 Feb 2026

Bobby in the Lobby

Tennessee Williams Theatre 7 Mar 2026

Changes In Latitude at Key West Theater

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

A Night of OASIS at DURTY HARRY’S

Durty Harry's 27 Jan 2026

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

Key West Theatre 14 Feb 2026

New Years Eve at The Bali Bar with Cliff Cody & guest Aloha Steve

The Key West Hotel 31 Dec 2025

Martin Sexton at Key West Theater

Key West Theater 13 Mar 2026

DMTB: The Dave Matthews Tribute Band

Key West Theater 25 Feb 2026

Kash'd Out at Key West Theater

Key West Theater 16 Jan 2026

Mile 0 Fest Key West - 3 Day Pass (Thursday-Saturday)

Truman Waterfront Amphitheater 28 Jan 2026

Mile 0 Fest Key West - 5 Day Pass

Truman Waterfront Amphitheater 26 Jan 2026

Mile 0 Fest Key West - Tuesday

Truman Waterfront Amphitheater 26 Jan 2026

Jimmy Buffet’s The Coral Reefer Band at Coffee Butler Amphitheater

Coffee Butler Amphitheater 16 Jan 2026

The Phil Collins Experience - Tribute

Key West Theater 25 Jan 2026

Gabriel Rutledge

Key West Theater 14 Feb 2026

Mile 0 Fest Key West: Randy Rogers Band Kaitlin Butts & Tanner Usrey - Thursday

Truman Waterfront Amphitheater 28 Jan 2026

Speaker Series: Karen Dukess

700 Fleming St, Key West, FL, United States, Florida 33040 9 Feb 2026

Mile 0 Fest Key West: Paul Cauthen Cody Canada and The Departed & Them Dirty Roses - Friday

Truman Waterfront Amphitheater 29 Jan 2026

Key West M**der Mystery: Catch the Killer!

400 South St 28 Jun 2025

The Music of ABBA at Tennessee Williams Theatre

Tennessee Williams Theatre 21 Jan 2026

The Massacoustics at Key West Theater

Key West Theater 4 Feb 2026

Margaritaville at Sea Cruise Ship Special

Key West Rebecca 15 Dec 2025

Southernmost Republican Club Holiday Party and Elections

Key West Yacht Club 15 Dec 2025

Kaitlin Butts in Key West

Truman Waterfront Park Amphitheater 29 Jan 2026

Early Bird Clean Up Duval & Eaton Streets hosted by Key West Woman's Club

Key West Woman's Club 9 Jan 2026

Amazing Scavenger Hunt Adventure - Key West, FL

Flagler Station Museum 2 Jul 2015

Los Lobos

Key West Theater 12 Jan 2026

Key West Scavenger Hunt Walking Tour & Game

420 Wall St 17 May 2025

Mangoes Drag Brunch Royale - Benefitting Sister Season Fund

Mangoes Restaurant 21 Dec 2025

WOOF Week 2026!

1129 Fleming St, Key West, FL, United States, Florida 33040 21 Apr 2026

Amazing Scavenger Hunt Adventure - Key West, FL

Key West Historic Seaport, William Street, Key West, FL, USA 21 Jun 2025

The Phil Collins Experience

Key West Theater 27 Jan 2026

A Date Night Adventure! - The Beauty of Key West

115 Front St 24 Jul 2025