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. 

Papio Kinetic Sculpture Parade

Papio Kinetic Sculpture Parade

Apr 3 2020 - 8:30am to Apr 5 2020 - 4:30pm
If one man's junk is another man's treasure, then the late Key Largo folk artist Stanley Papio was a treasure hunter extraordinaire. Fans of "outsider art" can celebrate the renegade metal sculptor's legacy with a people-powered parade of mobile sculptures crafted in the spirit of...Read more
Conch Republic Flag

Annual Conch Republic Independence Celebration

Apr 17 2020 - 8:00am to Apr 26 2020 - 6:00pm
With activities such as a lighthearted sea battle featuring tall ships, the Conch Republic's 10-day birthday party showcases the independent and eccentric spirit that characterizes the Florida Keys. Recommended Nightly Vacation Rentals: Casablanca — 1 Bedroom, 1 Bath, Sleeps 4 Casablanca Grande — 2 Bedrooms,...Read more
Key West Songwriters Festival

Key West Songwriters Festival

May 6 2020 - 4:45pm to May 10 2020 - 4:45pm
The annual showcase of musical magic features America's foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. The largest festival of its kind in the world celebrates 24 years as both a tourist attraction and favorite of island locals. The festival revolves around...Read more
Key West Pride

Key West Pride

Jun 3 2020 - 8:00am to Jun 7 2020 - 4:45pm
Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair,...Read more
Colored Baskets

Bahama Village Goombay Festival

Oct 16 2020 - 12:00pm to Oct 17 2020 - 11:45pm
Held in Key West's historic Bahama Village neighborhood, the lively, family-friendly Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visitors can experience sights, sounds and flavors recalling Key West's Bahamian heritage. FREE event, noon to...Read more
Key West Fantasy Fest

Key West Fantasy Fest

Oct 16 2020 - 8:00am to Oct 25 2020 - 5:00pm
This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats.Read more
Florida Keys Seafood Festival

Florida Keys Seafood Festival

Jan 16 2021 - 8:00am to Jan 17 2021 - 8:00pm
Save the dates for the Annual Florida Keys Seafood Festival in Key West January 16 & 17, 2021 for the freshest seafood caught, cleaned, prepared & served by your local fisherman. $5 admission good for BOTH Saturday & Sunday. This event is a fundraiser for...Read more