Fun, sun, sand, and warm temperatures year-round make Florida one of the best spots for a getaway any time of the year. If you’re looking for all that along with a bit of fall flair, you’ll find everything you’re looking for in Siesta Key this fall season. There are plenty of fall activities, festivals, and fun things to do in Siesta Key to keep you happy, busy, and in a crisp, fall mood throughout your stay.

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Whether it’s the beat of the sun on a hot summer day or a crisp fall day, your island vacation won’t be complete without a visit – or two or more – to the beach. Pack your beach gear and make the short trip to the beach for some much-needed beach time and R&R. While swimming in the shimmering waves of the Gulf might not be on the list, you can still sit out in the sun and enjoy the weather by sunbathing or reading a book. Take a walk or run on the beach for some exercise or brave the cooler water for adrenaline-pumping activities like jet skiing, or parasailing.


When summer turns to fall, many locales across the country celebrate their own version of Oktoberfest. The festival, which started in Germany, spread around the globe and now people everywhere get together to share beer, music, games, festivals, and more. The island may celebrate a little differently from the mainland, but there are nearby mainland locales that may offer a bigger party.

Sand Sculpting Festival

There can’t be anything more appropriate to celebrate on an island than sand sculpting. The International Sand Sculpting Festival takes place every November in Siesta Key. These are not your average sandcastle built with a pail and a bucket at the water’s edge. From large, intricate castles with carved details including windows and doors to life-size replicas of famous people, sculptors go all-out to showcase their skills and talent. You can buy tickets for the event on their website. Afterward, try your hand at building your own sand sculpture.

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Stroll the streets of Siesta Key or hike its beautiful many trails. Fall is one of the best times, as the weather is cooling down but still warm enough to keep you comfortable. Explore everywhere your feet can take you that your rental car can’t. Pack your essentials – like water, sun gear, and whatever else you need, and set out on an adventure. Make sure one of those essentials is your camera, as you’re bound to spot some of the island’s wildlife while you’re out.

Bicycle Rentals

Keep the rental car parked at your accommodations and gather your loved ones for some exercise. Explore the many walking and biking trails leading to all the nooks and crannies of Siesta Key where your motor vehicle just can’t go. Bike rental companies offer an array of options, from cruisers or mountain bikes, adult-size tricycles for added basket space and balance, romantic bicycles built for two, children’s bikes, and adult bikes outfitted with baby seats. Ask about locks, extra baskets, other accessories, and safety gear like lights and helmets. There may even be perks like delivery to your accommodations.


After you’ve walked, hiked, or biked your way around the island, hop on the free trolley for a different type of wheeled transportation. Save the gas in your rental car for an off-island trip and conserve your own energy for the fun you’ll have at your destination when you take the Siesta Breeze Trolley to just about any destination on the island. Experience the fun, free, round-trip service from Siesta Key Village all the way to the southernmost part of the island, with many stops in between. Get on or off at any stop and spend as long as you like at the location before meeting the trolley at another stop or when it comes back your way.

Fall Fun in Florida

When you book a fall getaway with Rent Siesta Key, you won’t be short on fun activities to fill your time while you’re here. You’ll be able to design a getaway that is uniquely yours with memories to last a lifetime. Relax and unwind after a fun-filled day with loved ones. Enjoy a one-bedroom for your small family or sweetheart getaway, all the way up to six bedrooms for a larger group. If you don’t want to go out to eat, make a group meal in your unit’s fully equipped kitchen. Enjoy the meal in the dining area, or in a private outdoor space like a patio or balcony. At the end of the day, relax in a private bedroom. Opt for a premium unit that may include perks like a fireplace, double ovens, stainless steel appliances, flat-screen TVs, a private pool – some even screened in for added protection from the Florida sun and more. Include everyone by asking about select rentals that allow your fur babies to stay.

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Contact us today to book your fall Florida getaway in Siesta Key!