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. 

Key West Triathlon

Dec 15 2024 - 7:30am
December 15 Key West Key West Triathlon Website The Key West Triathlon begins and ends at College of the Florida Keys, 5901 College Rd., shifting from the traditional location because of ongoing construction along S. Roosevelt Avenue. All fitness levels are welcomed. Races include the...Read more
Holiday Events
Nutcracker

Nutcracker Key West

Dec 5 2024 - 7:30pm to Dec 15 2024 - 7:30pm
December 05 - 15, 2024 Key West Nutcracker Key West Website Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens,...Read more
Holiday Events

Old Town Trolley: Holiday Nights Tours

Dec 9 2024 - 7:45pm to Dec 23 2024 - 7:45pm
December 09 - 23, 2024 Key West Old Town Trolley: Holiday Nights Tours Website Take the trolley for a tour of the Key West residential neighborhoods known for going all-out with holiday home decorations. Make this your new holiday tradition with friends and family. Narrated...Read more
Holiday Events

Key West Holiday Fest

Dec 1 2024 - 10:15am to Dec 31 2024 - 11:15pm
December 01 - 31, 2024 Key West KEY WEST HOLIDAY FEST WEBSITE A merry range of celebrations during Key West's busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good...Read more
Holiday Events
key west songwriters festival

Key West Songwriters Festival

Apr 30 2025 - 7:00am to May 4 2025 - 11:30pm
SAVE THE DATE!! 29th Annual Key West Songwriters Festival April 30 - May 4, 2025Read more
Upcoming Events
key west pride

Key West Pride

Jun 22 2025 - 8:00am to Jun 29 2025 - 5:00pm
June 22 - 29, 2025 Key West KEY WEST PRIDE WEBSITE Celebrate PRIDE on the tropical island of Key West that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or to...Read more
Upcoming Events

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