Key West Events Calendar

Key West Film Festival 2019

Key West Film Festival 

November 20-24, 2019

Showcasing films that exhibit excellence in storytelling, the festival's lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers. 


Get ready for your closeup with a beautiful cottage or condo from Historic Key West Vacation Rentals. 

Key West Lighted Bike Parade Event

Key West Lighted Bike Ride

December 4, 2019


The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Entry for the bike ride is an unwrapped toy or monetary donation for Holiday Helpers. Wesley House Family Services coordinates this bike ride - registration begins October 1 online. This year the Coke Florida Caravan will be in Bayview Park to provide free photos with Santa along with cookies (from Winn Dixie) and milk - 5pm – 7:30pm. The Lighted Bike Ride will leave Bayview Park at 7pm Entry fee for the Bike Ride is one unwrapped toy for Holiday Helpers or monetary donation


Light up the holidays with a beautiful cottage or condo from Historic Key West Vacation Rentals.

Florida Keys Seafood Festival 2020

15th Annual Florida Keys Seafood Festival

January 18 - 19, 2020


Save the dates and enjoy the freshest seafood caught, cleaned, prepared & served by your local fisherman. $5 admission good for BOTH Saturday & Sunday. This event is a fundraiser for the Florida Keys Commercial Fishermen's Association (FKCFA) and goes to support sustainable fishing programs, marine restoration projects & college scholarships.


Reserve a beautiful cottage or condo from our collection and SAVE when you Book Direct with Historic Key West Vacation Rentals.


21st Annual Key West Half Marathon & 5k Run

January 19, 2020


Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West's balmy January climate. Named as one of the United States' leading winter half marathons, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by


Spring on over to Historic Key West Vacation Rentals to reserve your beautiful cottage or condo for the race!

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.



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.

Papio Kinetic Sculpture parade

Papio Kinetic Sculpture Parade 

May 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 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. 


Enjoy the parade and 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.