Key West Events Calendar

January 25 - 26, 2020

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 and crafters who gather to display their talents at this popular outdoor festival on lower Whitehead Street in historic Old Town Key West.

Key West Food & Wine Festival

January 26 - February 2, 2020 


Top chefs and restaurateurs display culinary creativity and the Keys' indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively "Old Town Uncorked," neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting. 


A beautiful cottage or condo from Historic Key West Vacation Rentals makes the perfect pairing for these wines!

Mile 0 Music Festival Key West

Mile 0 Fest Key West 

January 28 - February 1, 2020


Mile 0 Fest Key West is a new music festival considered a "must see" in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Many activities and memorable experiences await.


Enjoy the music and a beautiful cottage or condo from Historic Key West Vacation Rentals.



March 07

An island tradition for over 50 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make "music" with fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10 a.m., contest starts at noon.

March 28

Underwater and outdoor enthusiasts, eco-travelers and families are encouraged to celebrate the marine environment at Mote Marine Laboratory's annual event. Proceeds and donations from the festival support Mote’s coral reef restoration and research programs. The family-friendly fun will take place from 10 a.m. to 4 p.m. at the Florida Keys National Marine Sanctuary's Eco-Discovery Center and Truman Waterfront, 35 E Quay Road.

April 03 - 05, 2020

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 his extraordinary creations. The Papio Kinetic Sculpture Parade (April 4) features colorful sculptural floats, tricycles with exotically costumed riders, fantastically decorated bicycles and other moving works of art — all powered by human effort alone — and are to follow a route along the length of Key West's Duval Street.

Conch Republic Festival Key West

Annual Conch Republic Independence Celebration 

April 2020


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.


Celebrate your independence with a beautiful cottage or condo from Historic Key West Vacation Rentals.

Key West Songwriters' Festival 

May 6-10, 2020


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 five days and nights of big stars in intimate settings, introducing audiences to the faces, voices and stories behind the songs.


Enjoy a beautiful cottage or condo from Historic Key West Vacation Rentals.

Key West Pride Festival

Key West Pride

June 3-7, 2020 


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, and pageants to select Mr., Miss and Ms. Key West Pride. 


Enjoy your Pride and a beautiful cottage or condo from Historic Key West Vacation Rentals.

Key West Fantasy Fest

October 16-25, 2020



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. 


Celebrate your fantasy with a beautiful cottage or condo from Historic Key West Vacation Rentals.

Bahama Village Goombay Festival 

October 23/24, 2020


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 midnight both days.


Celebrate island life with a beautiful cottage or condo from Historic Key West Vacation Rentals.