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.
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.
RokIsland Fest is a 4-Day Rock Music Festival located on the island paradise of Key West, Florida
The 2022 Key West Half Marathon will take place during the week-end of January 15-16, 2022
The Southernmost Regatta is 5 consecutive days of ORC Racing / Cruising Keelboats.
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.
Pet friendly event across from the White Street Pier.
Mile 0 Fest is a boutique destination festival bringing the best of Red Dirt & Americana Music to Paradise every year.
From 4-7 p.m. at Opal Key Resort & Marina, 245 Front St, a Cocktail Competition and tasting.
August Wilson takes us through a heartfelt theatrical memoir describing his journey through life's trials and tribulations.
Live at the Key West Theater located just a blocks from Duval.
The Chooi brothers are skilled violinists performing at St. Paul's Episcopal Church at 4pm.
Based on the iconic 1985 Paramount movie which was inspired by the classic Hasbro board game, Clue is a hilarious farce-meets-murder mystery.
The Silver Anniversary Gala hosted by "The Community Foundation"
Rams Head Presents: The Beach Boys
Live at the Coffee Butler Ampitheater
A festival commemorating locally caught seafood from local fisherman.
Details the history of how Conch Republic came to be. Follow the link to find tickets and reserve a spot to the show!
Partnered with Lagerheads Beach Bar & Grill to celebrate Earth Day featuring live music, games and a silent auction from 6-8pm
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.
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.
The festival is 5 days and 5 nights of live music throughout downtown Key West
Hosted by The Key West Business Guild with a timeline of events all week!
A 5-day festival through Fathers Day Weekend, that embodies the local community of Stock Island.
A family fun tournament with cash prizes!
Hosted by the Stock Island Marina & Village with nightly festivities leading up to an awards banquet.
33rd Anniversary Hemingway Key West 5k sunset run & paddleboard race. Registration open now!
The annual Lobsterfest is enjoyed by all, and features a schedule of events in downtown Key West
Hosted by the Rotary Club of Key West, a multi-day festival including a signature tasting event.
Womenfest offers a variety of activities for women from all walks of life. All are welcome!
The annual Key West Fantasy Fest returns to town for 10 days filled with costumes, libations and entertainment!