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

Sand Sculpting Festival

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


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 – to the beach. Pack your beach gear and make the short trip to the beach for some much-needed 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. You might try your hand at building your own sand castle like one you saw at the festival.


When summer turns to fall, many locals across the country celebrate their own version of Oktoberfest. The festival with German roots spread around the world 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.

Bicycle Rentals

Keep the rental car parked at your accommodations and gather the group for some exercise and a different way to explore Siesta Key. There are many walking and biking trails that take you to all the nooks and crannies of Siesta Key where your motor vehicle just can’t go. Many rental companies offer an array of options, from single-seat bikes with or without gears, adult-size tricycles for added basket space and balance, romantic bicycles built for two, children’s bikes, and adult bikes outfitted with baby seats. Make sure to ask about locks, extra baskets, other accessories and safety gear like lights and helmets. There may even be perks like delivery to your accommodations.


Stroll the streets of Siesta Key or hike its beautiful 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.


After you’ve walked, hiked, or biked your way around Siesta Key, hop on the free trolley for a different type of transportation on wheels. 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 in Siesta Key to fill your time while you’re here. From spending time celebrating the season at your rental to celebrating with visitors and locals alike at a festival, 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 your group. Enjoy a one-bedroom for your small family or sweetheart getaway, all the way up to six bedrooms for a larger group or reunion. For more privacy, choose a single-family home with garage. If you don’t want to go out, 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, or gather the group for a TV show or movie. Opt for a premium unit which may include perks like a fireplace, double ovens, stainless steel appliances, flat screen TVs, private pool – some even screened in for added protection from the Florida sun. Include everyone by asking about select rentals that allow your fur babies to stay.

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

The warmth and sun of Florida is an attraction any time of year. Pack your bags and prepare for fun in the sun, water, and even on land as you check out many of the exciting activities the area has to offer. While the weather may be perfect for the majority of your trip, you’ll want to prepare some activities for times when the weather doesn’t cooperate with your beach and outdoor schedule. There are many “rainy day” activities in Siesta Key to enjoy and pass the time when the weather is gloomy.

Siesta Key Village Shops

Touring a town is a great way to get to know its nooks and crannies as well as the locals. When the sun isn’t shining, that doesn’t mean that the exploration needs to stop, just take it indoors! The charming shops and restaurants found in Siesta Key Village will give you hours of fun, browsing, window shopping, and delicious food to keep your mind off of the pitter-patter of rain outside. You’ll score some great island-themed décor, clothing, and accessories to put on display once you get home and turn your home into an island getaway.

Siesta Key Wine Bar

An activity made especially for the adults of the group is a visit to Siesta Key Wine Bar. The self-billed “home for wine lovers,” the establishment at the north end of Siesta Key Village includes a tasting bar and sitting areas for you to enjoy a glass of terrific wine. The wine bar features local Florida wines, as well as reds, whites, and “bubbles” from across the globe. Visit the wine shop to take home your favorites or arrange to have your favorites shipped to your home. Keep in mind there is limited ability to ship to certain locales and yours may not be available.

Spa Day

While your outdoor relaxation plans may be canceled, that doesn’t mean the relaxation can’t take place indoors. Book yourself some time for rest, relaxation, and rejuvenation at a local spa. Choose from treatments like a mani/pedi, massage, body wrap, facial, and more. Staff will help you create a package just for you so you can fully relax your mind, body, and spirit. Some establishments may offer salon services, so you can get a new cut or style to go with your relaxed mood. Ask about treatments designed especially for the men of the group who need a recharge.

Relaxing Rental

You don’t need to go out on the town for a good time, indoors or out, rain or shine. You can always choose to relax around your Rent Siesta Key vacation rental home. Many rentals include books, a movie library, board games, puzzles, and other indoor activities to keep you busy. Staying right where you are can be just as engaging as a day out touring the town. If you have any personal favorite games from home, make sure they make the packing list so you can enjoy those, too, if the mood strikes.


Lift your spirits as the rain falls with a meal out on the town. There are many restaurants on Siesta Key that will satisfy any hunger or thirst you may have. From a casual lunch or dinner to a special date or celebration, you’ll find something delicious to fit the mood.


If the rain insists on lasting another day, or you’ve worn out all the things to do on-island, take a trip to the mainland for some fun. Sarasota is full of fun, with activities like museums, escape rooms, and aquariums, you’ll find something to do to battle the gloom and continue to enjoy your Florida getaway, no matter what the weather is like.

Rainy Day Fun Activities in Siesta Key

When you book your fun-filled getaway to Siesta Key, you won’t be short on activities to fill every minute of every day, even when the sun isn’t shining. With plenty of activities in Siesta Key to choose from, you’ll find something to do to keep the entire group entertained and happy without the sun. Spend some time in your accommodations if you don’t feel like going out. From a one-bedroom for your small family or a getaway with your sweetheart, all the way up to six bedrooms for a family or group reunion with everyone, you’ll find something by Rent Siesta Key to fit your vacation needs and style.

Instead of getting wet when heading out to eat, stay warm and dry and prepare a delicious home-cooked meal in your rental’s fully equipped kitchen. Recharge with a nap or a good night’s sleep in a private bedroom or spread out in the spacious living area to read a book or watch a movie. Indulge yourself in a premium unit for perks and upgrades like stainless steel appliances, double ovens, flat-screen TVs and much more.

Contact us now to book your stay full of all-weather memories!