Updated August 2026
Florida is a fantastic vacation destination year-round, but one of our favorite times of the year is fall. The weather is cooler, the summer crowds have dwindled, and the season is full of fun festivities. Experience the best of the season in the Tampa Bay Area and plan your getaway around one of our exciting annual fall events. With a vacation rental from Plumlee Gulf Beach Realty, you’ll have the perfect home base to relax and enjoy the fall season in Florida. Discover fun for the whole family at these local events:
Busch Gardens Halloween Spooktacular, September 5-November 1, 2026
Visit Busch Gardens and trick-or-treat around the park on Saturdays and Sundays during the Halloween Spooktacular event. Other activities include costume parades, storytimes, dance parties, and kid-friendly rides.
Offshore Nationals in Clearwater, September 25-27, 2026
Witness over 90 race boats competing for the winning title at the Offshore Nationals event in Clearwater. Watch the race from Pier 60 and stick around for the evening parties and live music celebrations.
Oktoberfest in Indian Rocks Beach, October 10, 2026
Oktoberfest returns to Indian Rocks Beach for another year of German festivities at Kolb Park! Join the celebration and enjoy a day of live music, German beer and food, art vendors, and keg-throwing contests.
Clearwater Jazz Holiday, October 15-18, 2026
Whether you’re a jazz music enthusiast or simply want to enjoy live music in the Florida sunshine, the Clearwater Jazz Holiday is the perfect event for you. This annual event offers four days of live performances at the beautiful Coachman Park, located in the heart of downtown Clearwater.
Sanding Ovations, November 19-22 & 28-29, 2026
Every November, master sand sculptors head to the beaches of Treasure Island to create one-of-a-kind works of art using nothing but sand and buckets of water. Head to the beach for this year’s Sanding Ovations and watch the sculptors bring their art to life. While you are here, you can also listen to live music, sign up for sand sculpting lessons, shop for crafts, and watch fireworks.
Book Vacation Rentals on the Florida Gulf Coast
From live music festivals to haunted houses, there is something for everyone’s interests on Florida’s Gulf Coast this fall. Plan your trip with Plumlee Gulf Beach Realty and reserve one of our vacation homes in Indian Rocks Beach or Indian Shores. Our properties offer the perfect combination of seclusion and convenience, located away from the busier beach towns while still being within driving distance of them all. Find the right property with the help of our Reservationists at 866-921-1166.
