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The warmth and sun of Florida is a major attraction any time of year. Lounging in the sun or splashing around in the water of the Gulf of Mexico is a fun and relaxing way to while away the time on a Florida getaway, but you’ll want to make sure to experience some of the Siesta Key Halloween fun and excitement when you plan a fall break around one of the spookiest days of the year.

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Siesta Key Safe Treats

Trick or Treat on Siesta Key is safe and fun, thanks to the Siesta Key Chamber of Commerce. The 37th annual Safe Treats for Kids is an event where merchants across the island will be handing out sweets and treats to costumed children. The afternoon event is a fun, relaxed event and the free Siesta Key Breeze Trolley can help you get between Siesta Key Village and Turtle Beach so you can maximize the fun. The free event is Saturday, October 30 from 1-4 p.m. at participating businesses across the island.

Sarasota Dog-O-Ween Costume Contest

If your furry friend made the trip with you, grab the leash and your fur baby’s costume and head to the Sarasota Annual Dog-O-Ween costume contest. Humans bring their canine companions to Paul Thorpe Park for some Siesta Key Halloween fun at the Sarasota Farmers Market Halloween Festival. Canines dress in their howl-o-ween best to compete for prizes including a complimentary exam donated by the Animal Medical Clinic at Rosemary, a gift basket full of toys donated by New Barker Magazine, and a $50 cash prize donated by the Sarasota Downtown Enrichment Association. The contest is Saturday, October 30. Registration is from 9-9:45 a.m. and the costume contest starts at 10 a.m. The cost is $5, and proceeds benefit the Donte’s Den Foundation. Keep in mind contestants must be leashed at all times and no retractable leashes are allowed. Make sure your dog visits the potty before the contest starts!

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Ghost Stories & Tours at The Point

You’ll have to take a short trip to the mainland for this ghostly fun. Marie Selby Botanical Gardens historic Spanish Point campus in Osprey is leading spooky stories and ghost tours at Spanish Point. Take a tour led by storytellers as they reveal the spookier history of the Spanish Point campus. Tours take place from 7:30-9 p.m. October 28-30. Admission is $15 for all Selby Gardens members and $20 for non-members. Guests must be 8 years old or older to participate.

The Monsters Cruise

An adults-only party, the Monsters Cruise invites all witches, ghouls, zombies, monsters, and other scary spirits aboard the LeBarge. There will be a full bar and snacks available throughout the night for purchase aboard the vessel. Come in your Halloween best. There will be plenty of adults-only Halloween fun on board, including a drag show. The cruise sets sail Saturday, October 30 and sails from 9-11 p.m. This event is for guests 21 years old and up. If you don’t want the fun to end, look for other events at local restaurants and bars that take place before or after the cruise.

Choose Your Own Adventure

Don’t forget you came to Siesta Key to rest and relax in the Florida sun as well as to have some Halloween fun. There are plenty of indoor and outdoor activities that don’t necessarily have a spooky theme. Gather your group and head to the beach for swimming, stand-up paddleboarding, sandcastle building, and more. Get out to some of the indoor attractions like escape rooms, museums, galleries, restaurants, shopping and an endless number of other activities. You can also choose to decorate your rental with removable, non-damaging decorations or create a Halloween-themed scavenger hunt or other activity that keeps you closer to home and away from the larger crowds of official events.

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Siesta Key Halloween

When you book your spooktacular Halloween getaway to Siesta Key, you won’t be hard pressed to find something to fill every minute of every day of your trip. Fuel up for the day or bring the group together with a delicious home-cooked meal prepared in your unit’s fully equipped kitchen. When the spooky fun is done for the day, relax in a private bedroom, or spread out in the open living area for a game, movie, or TV show. When you’re not at the beach or soaking up the Halloween fun, enjoy some outdoor time on a private patio or balcony. Choose a premium unit for stainless steel appliances, double ovens, flat screen TVs, and more. Rent Siesta Key has a rental to fit your needs, from one-bedroom units for your small family or spookily romantic getaway all the way up to six bedrooms for a Halloween reunion with friends or family.

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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:

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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.

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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.

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Fun Fall Activities in Siesta Key, 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.

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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.

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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.

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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.

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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.

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