Key West Events Calendar

From annual festivals to holiday celebrations, the fun never stops in Key West. We're looking forward to these upcoming Key West events. For details on any event or planning a holiday vacation, contact our local team! We're happy to provide nearby vacation rental recommendations and the inside scoop on all things Key West. 

Mile 0 Fest

Mile 0 Fest

Jan 24 2023 - 7:00am to Jan 28 2023 - 11:00pm
Mile 0 Fest Key West is a new music festival considered a "must see" in the burgeoning Red Dirt & Americana music scene.Read more
key west food and wine festival

Key West Food & Wine Festival

Jan 25 2023 - 10:30am to Jan 29 2023 - 7:30pm
The Key West Food and Wine Festival is a series of wine and food themed events, showcasing a diverse range of wines and inventive cuisine, hosted by their passionate creators and iconic Key West locations.Read more

Key West Craft Show

Jan 28 2023 - 7:30pm to Jan 29 2023 - 7:30pm
The Key West Craft Show is a two day juried outdoor craft festival. This nationally recognized Craft Show brings over 100 fine and skilled craft artists to this beautiful historic area of Key West. Tens of thousands of attendees browse and buy among juried artisans...Read more
kelly mcgillis classic

Kelly McGillis Classic International Women & Girls Flag Football Championships

Jan 24 2023 - 8:00am to Jan 30 2023 - 11:00pm
Women from countries far and wide will be descending upon Key West for flag football competition, fun and learning. It is anticipated this event is to represent the most international countries, and organizers have hosted teams from USA, Morocco, Spain, Mexico, India, Jamaica, Honduras, El...Read more
key western fest

Key Western Fest

Jan 31 2023 - 9:45am to Feb 4 2023 - 11:45pm
Jan. 31st-Feb. 4th 2023 Key Western Fest is four days and nights of country music's best! Music will be played all over the island during the day and at the Amphitheater at night. See The Marshall Tucker Band, The Oakridge Boys, Clint Black and more!...Read more
key west songwriters festival

Key West Songwriters Festival

May 3 2023 - 7:00am to May 7 2023 - 11:30pm
The Key West Songwriters Festival -the largest festival of its kind in the world. Since 1997 BMI has been a presenting sponsor of the festival and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five...Read more
fantasy fest

Fantasy Fest Key West 2022

Oct 20 2023 - 8:00am to Oct 29 2023 - 5:00pm
Started in 1979 by Key West Locals, this 10-day parade has turned into one of the best and biggest parties Key West has to offer!Read more