The 5 Best Key West Events For Every Traveler in 2025
Year after year, Key West beckons travelers from all areas to its vibrant neighborhoods and island-life culture. From eclectic events to sun-soaked beach-going, there’s so much to do and see for every kind of paradise-seeker—including a calendar full of festivities worth paying a visit.
Parrot Key Hotel & Villas puts you in perfect proximity to the center of it all. With oceanside accommodations just a shuttle’s trip away from the heart of the fun on Duval Street, Parrot Key is an idyllic home base for this year’s events and festivals. Let our waterfront oasis help you relax, unwind, and gear up for all the memories that await. So pack your bags and mark your calendars—here are the top five Key West events you won’t want to miss in 2025.
Florida Keys Seafood Festival (February 15-16, 2025)
Calling all foodies! Prepare to sink your teeth into the freshest flavors of the Florida Keys. The 19th Annual Florida Keys Seafood Festival is a celebration of fresh seafood, live music, and family-friendly activities. Indulge in fried fish baskets, Stone Crab Claws, Key West Pink Shrimp, and other savory classics while washing it down with a rum runner or two—and don’t forget to save room for a slice of key lime pie! With raffles, shopping, live entertainment, and a children’s Eco Discovery Zone, this festival makes for the perfect day spent with family and friends.
Key West Pride (June 22-29, 2025)
Known for its laid-back style and accepting island atmosphere, Key West gears up to host yet another memorable Pride celebration in 2025. Key West Pride features a lively roster of parades, events, and street fairs lined down Duval Street, welcoming all LGBTQ+ visitors, friends, and allies. From daytime water adventures to late-night drag shows, this week-long celebration is rooted in integration, acceptance, and inclusions—and a whole lot of fun.
Just a Few Friends Key West (August 29-September 1, 2025)
For the ultimate Labor Day getaway, plan a day (or two) at the 2nd annual celebration honoring the Florida Keys’ favorite son, Jimmy Buffet. The Just a Few Friends Key West memorial celebration is filled with bar crawls, rum tastings, and music events to create an unforgettable weekend. Kickstart the party with the Second Line Memorial Parade down Duval Street, then let the fun lead you to a free music festival at Truman Waterfront Park—there’s no better setting to raise a glass to the legendary trop-rock singer.
Key West Fantasy Fest (October 17-26, 2025)
Even after the busy summertime ends, the Florida Keys never stop buzzing with eclectic energy. Each fall season welcomes the iconic Key West Fantasy Fest—a one-of-a-kind experience you won’t want to miss. The annual 10-day costume and masking extravaganza, Fantasy Fest, is home to exciting and exotic events, including a Headdress ball, Masquerade March, and world-famous parade. This year’s theme is “Bedtime Stories & Magical Monsters,” so round up your fun-loving friends and come dressed in your magical best!
Key West Holiday Fest (November 26- December 31, 2025)
Everyone dreams of spending a holiday surrounded by ocean waves and swaying palms—let 2025 be the year dreams become reality! The Key West Holiday Fest is the perfect reason why, and an easy way to fill your end-of-year calendar with seasonal fun for the whole family. From the iconic Harbor Walk of Lights to the lighted boat parade to the festive artisan markets, this season-long celebration is packed with merriment and memories.
Make Parrot Key Your Floridian Base
No matter the season, Key West radiates vibrancy and island spirit all year long thanks to an array of exciting events, fests, and celebrations.
To prepare for an action-packed itinerary, let Parrot Key be your escape for rest and relaxation. With modern, spacious accommodations—including an array of rooms, suites, and private villas— and serene surrounding landscapes, you’ll find solace in our oceanside oasis. Our on-site amenities are sure to elevate every aspect of your stay, from sunbathing with Beach Club access to poolside sipping with complimentary refreshment tasters served every hour.
After waking up each morning to the calming ocean waves or the crow of a rooster, hop onto our complimentary shuttle that brings you right to Duval Street, knowing a paradise hideaway awaits when the adventurous day is done. Then, wind down each evening by toasting to the memories made with island-inspired cocktails at The Grove Kitchen & Bar.
Parrot Key is here to turn your vacation plans into cherished memories with family and friends. Start planning your travels today by discovering our best offers and promotions.
