As the summer crowds thin, Siesta Key blossoms into a peaceful paradise with a calendar full of exciting fall events. Plan a Siesta Key getaway for September or October 2025. It’s the perfect time to visit, and RVA offers exceptional vacation rentals right on the Key to make your stay unforgettable. From local festivities to cultural highlights, here’s what you can look forward to.
September: Culture and Community on the Gulf
September in Siesta Key is a blend of local business events and cultural highlights that offer a taste of the area's vibrant community.
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Cultural Cinema and Opera: The nearby Sarasota Opera House is a hub for culture. Every Friday you can catch classic films like The Last Picture Show at the opera house and indulge in an elevated cinema experience. Check out the calendar of upcoming films here. What’s an opera house if not for operas? Get a head start on the season with the Sarasota Opera House’s pre-season HD at the Opera series and experience the comedy of Ariadne auf Naxos and the tragedy of Otello before the dramatic opening of the season. Check out the calendar of upcoming HD at the Opera showings here. Cap off your visit with the Sarasota Opera's annual Food & Wine Festival! This community event features a variety of eateries with tasty food samples and wine tastings. Get all the tasty details here.
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Siesta Key Farmers Market: Every Sunday, you can stroll through the Siesta Key Farmers Market in Siesta Key Village, a year-round event where you can find fresh produce, crafts, and local treats. Learn more about the farmers market on their Facebook page. We highly recommend trying some of the local craft rum and pepper jelly!
October: Spooky & Spectacular
October brings a festive, spooky spirit to Siesta Key with events that are perfect for families and couples alike.
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Sarasota Boos & Booze Halloween Bar Crawl: For the grown-ups, get your costumes ready for the Sarasota Boos & Booze Halloween Bar Crawl on October 25th. This event takes place in Downtown Sarasota and features drink specials, costume contests, and a lively atmosphere (Source: Visit Sarasota).
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Siesta Key Scarecrow Stroll & Halloween Treats: Throughout the entire month of October, the Siesta Key Scarecrow Stroll will feature creative, homemade scarecrows lining the village. The month concludes with a family-friendly “Safe Treats” Halloween event in Siesta Village on October 31st, making it a perfect spot for some spooky fun. Get more details about this spooky and fun event here.
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WONDERBALL 2025: the ultimate electronic dance music fundraiser, returns for its third epic year bigger, bolder, and more electrifying than ever. This high-energy, one-night-only event fuses cutting-edge EDM with the magic of the circus. WONDERBALL 2025 promises a high energy night of dance music, lights and impact. This event has sold out the past two years and they expect to sell out again so do not delay! WONDERBALL 2025 is an all ages welcome event. WONDERBALL 2025 takes place on Saturday, October 4, 2025, at 7:00 p.m. at the Sailor Circus Arena.
Your Siesta Key Home Away From Home
As you can see, Siesta Key is the perfect place to come relax, unwind, and enjoy one of the country’s most beautiful beaches. Select from a curated selection of hundreds of vacation rentals right on Siesta Key. Imagine waking up to the sound of waves, enjoying a coffee on your private balcony, and being just steps away from one of the nation’s top beaches. Our properties offer the comfort and amenities you need to make your Siesta Key fall vacation unforgettable.
Ready to book your Gulf Coast getaway stay? Explore our beautiful Siesta Key vacation rentals and secure your stay with RVA today at https://www.rvafl.com/.