Florida’s best festivals and events
Amp up your vacation fun all year round
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Florida is famous for its sunshine and sandy shores, but there’s a whole other side to the Sunshine State waiting to be discovered—its vibrant, year-round festival scene.
From pirate parades in winter to jazz-filled autumn nights, Florida’s calendar is packed with annual events that celebrate everything from art and music to food and local heritage. No matter when you book your getaway, there’s likely an unforgettable festival happening near your Vacasa vacation rental—turning every vacation into a fun-packed adventure.
This world-famous art festival ignites the city with cutting-edge art, dazzling installations, and vibrant parties—an unmissable celebration showcasing groundbreaking contemporary works from top galleries worldwide.
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Every January, Tampa transforms into a swashbuckling playground during the Gasparilla Pirate Fest. Watch as pirates “invade” the city in a lively family-friendly parade, then join the crowds for live music, street celebrations, and family-friendly activities.
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The South Florida Fair is a classic winter tradition, featuring thrilling amusement rides, a bustling midway, and mouthwatering food vendors. Wander through themed exhibits, catch live entertainment, and experience agricultural displays that highlight Florida’s rich farming heritage.
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Step back in time at Miami Beach’s Art Deco Weekend, where the iconic pastel architecture of Ocean Drive sets the stage for a 1930s-themed celebration. Enjoy vintage car shows, guided walking tours, live performances, and artisan markets.
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Celebrate the flavors of the Florida Keys at this vibrant festival, where foodies enjoy fresh local seafood, lively music, and family-friendly fun. Support local fishermen, browse unique crafts, and soak up Key West’s laid-back island atmosphere. Vacasa proudly sponsors this event.
Experience the charm of the nation’s oldest city while feasting on delicious seafood, enjoying live entertainment, and exploring artisan markets. This beloved festival blends coastal cuisine, culture, and community spirit for a memorable springtime outing. Vacasa proudly sponsors this event.
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Marvel at rare, vintage automobiles displayed on lush fairways at this prestigious event. Guests mingle with car enthusiasts, attend exclusive seminars, and witness automotive history come alive in an elegant, picturesque setting on Amelia Island. Vacasa proudly sponsors this event.
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Film buffs flock to Orlando each April for the Florida Film Festival, a showcase of independent films from around the world. Enjoy screenings, celebrity guest appearances, and insightful panels.
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A beloved tradition just outside of Tampa, the Florida Strawberry Festival combines a state fair vibe with sweet, local flavor. Savor strawberry shortcake, enjoy top-tier music acts, and let the kids loose on carnival rides.
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Disney’s Epcot transforms into a floral wonderland during this springtime festival. Marvel at intricate topiaries, themed gardens, outdoor kitchens, and interactive exhibits. The event blends Disney magic with horticultural artistry.
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Indulge in a world-class wine and culinary adventure along Florida’s scenic coast. Taste hundreds of wines, savor gourmet food pairings, enjoy live music, and participate in charity auctions—all while supporting children’s charities in a beautiful beachside locale. Vacasa proudly sponsors this event.
Celebrate the legacy of Ernest Hemingway in quirky Key West style. Hemingway Days features literary readings, a famed look-alike contest, and the offbeat “Running of the Bulls”—a playful nod to the writer’s adventurous spirit.
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South Beach becomes a runway during Miami Swim Week, where the latest swimwear trends are unveiled alongside glamorous parties, pop-up shops, and celebrity sightings.
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The skies above Pensacola Beach roar to life as the Blue Angels perform breathtaking aerial stunts. Families gather on the sand to watch the show, enjoy beach games, and soak up the festive atmosphere.
Fantasy Fest is Key West’s legendary 10-day celebration, famous for its elaborate costumes, vibrant parades, and island-style revelry. Themed parties, street fairs, and artistic displays fill the streets.
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Taste your way around the world at Epcot’s Food & Wine Festival. Sample global cuisine, sip fine wines, and attend culinary demonstrations—all set against the backdrop of Disney’s magical World Showcase.
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Enjoy smooth jazz and sea breezes at the Clearwater Jazz Holiday, an outdoor music festival set in a stunning beachfront park. Nationally acclaimed artists share the stage with local talent, creating a laid-back, family-friendly event.
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Here are some hacks to make the most of Florida’s lively festival scene:
Florida’s festivals offer something for every traveler, every month of the year. Browse Vacasa rentals to find your perfect festival home base, and get ready to discover the vibrant spirit that makes Florida a fun-filled, sun-soaked vacation in all seasons.
