Key West Events Calendar

Key Lime Festival 2019

Annual Key Lime Festival

July 2-5, 2020

 

A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the annual Key Lime Festival. Four days of culinary events for every taste are planned, including favorites from past years like the Key Lime Cocktail Sip & Stroll, and new favorites for Key Lime lovers like The Key Lime Pie Hop.

 

 

Put the lime in the coconut and reserve a beautiful cottage or condo from Historic Key West Vacation Rentals.

Key West Mermaid Festival

Key West Mermaid Festival 

July 5-7, 2019

 

Our crew and mermaid pod are over the waves excited to bring you this three-day weekend event, packed with so many fun and mervelous events. From "Mermaid Meet & Greets" and our "Sunday Funday with Mermaids", to mermaid vendors with a splash of entertainment and heaps of ocean awareness, dancing under the sea, and much, much more! With activities for the little mermaids and adult mermaids at heart, the Key West Mermaid Festival is an entire island family friendly event welcoming Florida Keys locals and visitors from across all of our oceans!

 

Enjoy a fin-tastic time and a beautiful cottage or condo from Historic Key West Vacation Rentals. 

 

Hemingway Lookalike Key West

Hemingway Days 

July 16-21, 2019

 

The 39th annual celebration of the legendary author's work and lifestyle features literary readings, the Running of the Bulls, a short story competition, fishing tournament, 5k Run and Paddleboard Race, Sloppy Joe's Look-Alike Contest and a birthday "party" commemorating Ernest's July 21st birthday. 

 

Celebrate "Papa" with a beautiful cottage or condo from Historic Key West Vacation Rentals. 

Key West Brewfest 2019

Key West Brewfest

August 29 - September 2, 2019

 

Nearly 200 beers and micro-brews are on tap at this "tasty" annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event (Aug. 31) are some of the offered activities.

 

Celebrate the brews with a beautiful cottage or condo from Historic Key West Vacation Rentals. 

Key West Womenfest 2019

Womenfest 2019 

September 4-8, 2019

 

Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America's Womenfest.

 

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

Fantasy Fest Key West

40th Annual Key West Fantasy Fest

October 18-27, 2019

 

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.

Key West Goombay Fest

Bahama Village Goombay Festival 

October 18-19, 2019

 

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.

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 2019

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.

KEY WEST HALF MARATHON and 5k

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 Competitor.com.

 

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

women's flag football

28th Annual Kelly McGillis Classic International Flag Football Championship

 

 

Women and girls from around the world are to meet on the playing field for hard-fought sporting action. Each year, nearly 30 teams from across the United States, Mexico, Central America, Sweden and India participate. 

 

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

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.