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"
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 Moteâ€™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!
The annual Lobsterfest is enjoyed by all, and features a schedule of events in downtown Key West
Key West BrewFest has grown to be the largest event put on by Key West Sunrise Rotary. The multi-day festival hosted by Southernmost Beach Resort includes beer pairing dinners, pool parties along with other activities around town culminating with the signature tasting event. Each day offers things to do with events taking place at many restaurants, hotels, and bars all over Key West.
Celebrate 400 Years of Nuestra Senora De Atocha. There will be five days of exciting events and special ceremonies.
Womenfest has a simple goal: to celebrate ALL women! Key West Womenfest offers a wide range of activities for those who want to socialize, feel comfortable being themselves, soak up some sun, then party and dance the night away.
A race around the continental United States' Southernmost island, presented by Lazy Dog Adventures. This 12-mile challenge includes paddleboards and other self propelled watercraft.
Legends of Music Row is coming to the Key West Coffee Butler Amphitheater. This year's special guest is the "King of Country" George Strait. Book your tickets today!
Fantasy Fest is back! Fantasy Fest is an annual 10-day party in paradise, for grown-ups only. This year's theme is Cult Classics and Cartoon Chaos.
Parrot Heads in Paradise gather to celebrate another year in paradise. Join this fun loving event for a week of dancing on the beach and other island celebrations. This is a nonprofit event inspired by Jimmy Buffet. The festival raises millions of dollars each year towards various charities.
The World's best offshore power boat teams compete for the championship in Key West Harbor.
Key West's busy holiday season includes the Harbor Walk of Lights, The Lighted Boat Parade, The Hometown Holiday Parade, trolley tours and other fun events for the whole family.
Ring in the New Year in Key West style!
The Key West Food and Wine Festival is a series of themed culinary events showcasing diverse wines and creative cuisines. Join us for this 14th annual festival with over 20 unique venues.
Fine Art lovers will enjoy creative offerings from over 100 artists. This open-air show takes place at Key West Truman Waterfront Park, from 10 am to 5 pm.
The Anne McKee Artists Fund (AMAF) was established in 1992 after its founder, Anne McKee, saw a pressing need to assist individual artists from Key West. Now, after more than 30 years, this non-profit organization supports an array of visual, literary & performance artists whose creative contribution adds to the quality of life throughout the Florida Keys
Celebrate 41 years of the Conch Republic. This is an annual event honoring Key West's quirkiness with silly events. Declare your Fun-dependence with humor and become part of Key West's One Human Family.
The largest singer-songwriter festival of it's kind in the World. Join us for 5 days of live music from up and coming performers and well known artist. This event takes place at some of the island's most popular Beaches, Boats, Bars, Resorts and Historic Theatres.
Celebrate PRIDE in Paradise. Key West is known for it's open and accepting atmosphere which makes the island so special. Join the party and experience the island's One Human Family philosophy.