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. 

pet friendly key west

8th Annual Parade of Paws

Dec 11 2021 - 10:00am
**Registration for your pet to become part of the Royal Court will be available this Fall** Join the Florida Keys SPCA for our 8th annual Parade of Paws at the Higgs Dog Park on Saturday December 11th from 10am-2pm. It will be a family friendly,...Read more
Key West Half Marathon and 5K

Key West Half Marathon

Jan 16 2022 - 7:00am
The 24th Annual Key West Half Marathon & 5k is a "bucket list" race.Read more
Florida Keys Seafood Festival

Florida Keys Seafood Festival

Jan 15 2022 - 8:00am to Jan 16 2022 - 8:00pm
Save the dates for the Annual Florida Keys Seafood Festival in Key West January 15 & 16, 2022 for the freshest seafood caught, cleaned, prepared & served by your local fisherman. $5 admission good for BOTH Saturday & Sunday. This two day celebration is a...Read more

Key West Food & Wine Festival

Jan 26 2022 - 7:30pm to Jan 30 2022 - 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 29 2022 - 7:30pm to Jan 30 2022 - 7:30pm
2022 marks the 36th Annual Key West Craft Show, a 2-day juried outdoor craft festival bringing over 100 fine and skilled craft artists to this historic area of Key West.Read more
mile 0 fest

Mile 0 Fest

Apr 25 2022 - 7:00am to Apr 29 2022 - 7:00am
Mile 0 Fest Key West is a new music festival considered a "must see" in the burgeoning Red Dirt & Americana music scene.Read more
Papio Kinetic Sculpture Parade

Papio Kinetic Sculpture Parade

Apr 30 2022 - 8:30am
Human powered art sculptures take over Key West at the Papio Kinetic Sculpture Parade!Read more
key west whiskey fest

Key West Whiskey Festival

May 26 2022 - 7:00am
This innaugural food, drink and music festival is one of the most eagerly awaited on Florida Keys’ busy social calendar. Featuring top class whiskey, Popular highlights will include a range of Tastings, Whiskey walks, Workshops, Brunches and plenty more.Read more

Key West Fantasy Fest

Oct 21 2022 - 8:00am to Oct 30 2022 - 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