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May 20th
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2022 Key West Events

Vacation Homes of Key West brings you an updated calendar of Key West Events to help you plan the trip you are dreaming about. Choosing a vacation rental property from Vacation Homes of Key West will provide you with a beautiful, and usually the most affordable place to stay for your favorite Key West events. If you are planning to come to the island for a more popular event, such as Fantasy Fest or New Years, we suggest you reserve your vacation rental well in advance so you don't miss out on your favorite place to stay.


January 2022

Matilda The Musical

Jan 12 to Jan 29

The award winning musical Matilda will preview at the Waterfront Playhouse on Wednesday January 12, with a grand opening on Thursday January 13 and playing Wednesday through Saturdays at 8pm through January 29.

Roks Island Fest 2022

Jan 14 to Jan 17

RokIsland Fest is a 4-Day Rock Music Festival located on the island paradise of Key West, Florida

24th Annual Key West Half Marathon & 5k

Jan 15 to Jan 16

The 2022 Key West Half Marathon will take place during the week-end of January 15-16, 2022

The Southernmost Regatta

Jan 17 to Jan 21

The Southernmost Regatta is 5 consecutive days of ORC Racing / Cruising Keelboats.

Key West 200

Jan 21 to Dec 11

On display in the Bryan and Bumpus Galleries at the Custom House Museum, 281 Front Street.The Key West Art & Historical Society announces the opening of Key West 200 commemorating the 200th anniversary of the first permanent settlement of Key West in 1822.

Florida Keys SPCA Artisan Market

Jan 23

Pet friendly event across from the White Street Pier.

Mile 0 Fest

Jan 25 to Jan 29

Mile 0 Fest is a boutique destination festival bringing the best of Red Dirt & Americana Music to Paradise every year.

Key West Master Chefs Classic Hosted by The Marc House

Jan 30

From 4-7 p.m. at Opal Key Resort & Marina, 245 Front St, a Cocktail Competition and tasting.


February 2022

Augst Wilson's "How I Learned What I Learned"

Feb 8 to Feb 12

August Wilson takes us through a heartfelt theatrical memoir describing his journey through life's trials and tribulations.

Rams Head Presents Tom Papa

Feb 11

Live at the Key West Theater located just a blocks from Duval.

The Chooi Brothers

Feb 13

The Chooi brothers are skilled violinists performing at St. Paul's Episcopal Church at 4pm.

Clue (Live On Stage)

Feb 16 to Mar 5

Based on the iconic 1985 Paramount movie which was inspired by the classic Hasbro board game, Clue is a hilarious farce-meets-murder mystery.

25th Anniversary Gala

Feb 17

The Silver Anniversary Gala hosted by "The Community Foundation"


March 2022

The Beach Boys at Coffee Butler Ampitheater

Mar 6

Rams Head Presents: The Beach Boys

Rams Head Presents The Price Is Right Live on Stage

Mar 26

Live at the Coffee Butler Ampitheater


April 2022

Florida Keys Seafood Festival

Apr 2 to Apr 3

A festival commemorating locally caught seafood from local fisherman.

Conch Republic - The Musical

Apr 21 to Apr 24

Details the history of how Conch Republic came to be. Follow the link to find tickets and reserve a spot to the show!

Reef Relief's 2nd Annual Luau Fundraiser

Apr 22

Partnered with Lagerheads Beach Bar & Grill to celebrate Earth Day featuring live music, games and a silent auction from 6-8pm

Mote Marine Labartory's Ocean Fest

Apr 23

A Saturday of activities hosted by Mote Marine Laboratory to showcase the local marine environment while raising money to benefit our oceans. Donations from the festival support Mote’s coral reef restoration and research programs.

Adam Lambert at Key West Ampitheater

Apr 28

Solo performance by Adam Lambert, who rose to fame in 2009 after finishing as runner-up on the eighth season of American Idol. He has performed alongside Queen as their lead vocalist over the years. Tickets available online.


May 2022

Key West Songwriters Festival

May 4 to May 8

The festival is 5 days and 5 nights of live music throughout downtown Key West


June 2022

Key West Pride

Jun 1 to Jun 6

Hosted by The Key West Business Guild with a timeline of events all week!

I Love Stock Island Festival

Jun 15 to Jun 19

A 5-day festival through Fathers Day Weekend, that embodies the local community of Stock Island.

9th Annual VFW Fishing Tournament

Jun 18 to Jun 20

A family fun tournament with cash prizes!


July 2022

Key West Marlin Tournament

Jul 20 to Jul 23

Hosted by the Stock Island Marina & Village with nightly festivities leading up to an awards banquet.

Key West Half Marathon & 5k

Jul 23

33rd Anniversary Hemingway Key West 5k sunset run & paddleboard race. Registration open now!


August 2022

26th Annual Key West Lobsterfest

Aug 11 to Aug 14

The annual Lobsterfest is enjoyed by all, and features a schedule of events in downtown Key West


September 2022

Key West BrewFest

Sep 2 to Sep 6

Hosted by the Rotary Club of Key West, a multi-day festival including a signature tasting event.

Key West Womenfest

Sep 7 to Sep 11

Womenfest offers a variety of activities for women from all walks of life. All are welcome!


October 2022

Key West Fantasy Fest

Oct 21 to Oct 30

The annual Key West Fantasy Fest returns to town for 10 days filled with costumes, libations and entertainment!


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