Buckle up because Siesta Key is gearing up to deliver the ultimate gift of holiday joy and island enchantment! This year, the holiday season promises to be more dazzling and memorable than ever before.
Whether you’re a lucky year-round resident who gets to experience holiday excitement regularly or a sun-seeking visitor eager to escape the winter chill, we’ve got something for everyone this season.
Join us as we take a deep dive into the shimmering sea of things to do in Siesta Key during this holiday season. Discover Siesta Key activities that will add a twinkle to your season, then unwind in our comfortable Siesta Key vacation rentals after a busy day!
Siesta Key Holiday Parade
Join the jolly Siesta Key Holiday Parade and let the holiday spirit sweep you off your sandy feet! Siesta Key is getting all dressed up with twinkling lights and festive cheer for this spectacular event on November 25th. The parade kicks off at 5.30 p.m. from Avenida del Mare and Beach Road and winds its way north on Beach Road and onto Ocean Boulevard, all the way into the heart of Siesta Key Village.
Expect to see local businesses and groups decked out in their holiday best, all coming together to give Santa the warmest welcome imaginable. And speaking of the big man himself, Santa will make his grand entrance at the Siesta Center right after the parade, ready to spread holiday happiness to all. Getting to the festivities is a breeze with free public transportation courtesy of the Siesta Key Breeze Trolley, running from Turtle Beach to Siesta Key Village. Hop on and let the holiday magic begin!
Selby Gardens Lights in Bloom
This enchanting event taking place throughout the holiday season is more than just a garden lit up with over two million twinkling lights – it’s a journey through a world of wonder! As you wander through this illuminated paradise, you’ll cross paths with radiant rainforest butterflies, dragonflies that twinkle like stars, and flowers that seem to burst into their own kaleidoscope of light. This event is not just about the lights either. You can capture unforgettable holiday photos to cherish for years to come, immerse yourself in exciting activities, and savor delicious food and beverages as you explore this illuminated wonderland.
47th Annual Sandy Claws Beach Run
Get ready to dash through the sand and soak up some sun at the 47th Annual Sandy Claws Beach Run! Hosted by Sarasota County Parks, Recreation, and Natural Resources, along with the Friends of Sarasota County Parks, this run is a beloved tradition in the vibrant Sarasota running community.
You can set your pace on the world-famous Siesta Beach sand in the thrilling 5K run or have a more leisurely start to your morning by taking a relaxing stroll along the picturesque shore in the 1-mile fun run. Whichever you opt for, all participants will proudly sport finisher medals. Custom awards are up for grabs for the top six finishers in each age category, too, so lace up those running shoes and aim for the podium!
But it’s not just about the run; there’s a whole beach party waiting for you. Groove to the beat of the music, savor delicious food and try your luck with exciting raffle prizes. Plus, it wouldn’t be a Sandy Claws Beach Run without the holiday-themed costume contest, so get creative with your festive attire. Mark your calendars and round up your friends and family for a sandy, sunny, and spectacular beach run that’s been delighting Sarasota for nearly half a century.
Sarasota Holiday Boat Parade of Lights
Prepare to be dazzled by the magic of the season on December 9th with this twinkling festival on Sarasota Bay, known as the Sarasota Holiday Boat Parade of Lights. This is a must-see for all ages, and the prime spots to catch all the boat parade action are City Island and Bayfront Park/Marina Jack in downtown Sarasota. Admission is free, making it a fantastic outing for families, friends, and anyone looking to immerse themselves in the holiday spirit.
Hosted annually by Suncoast Charities for Children and Marina Jack, this event is a true gem in Sarasota’s holiday calendar. Attendees are encouraged to bring along an unwrapped toy or book as these heartfelt donations will find their way to Suncoast Charities for Children, who will then distribute them to The Florida Center for Early Childhood, The Haven, and Children First. This is a great way to embrace the true spirit of the holiday season!
Christmas Glow Run
Get ready to dive into a dazzling holiday extravaganza with the Sarasota Christmas Glow Run 5k – the ultimate family-friendly event that’s sure to light up your holiday season like never before. The Sarasota Christmas Glow Run 5k promises to be an enchanting night as the city transforms into a winter wonderland of colorful Christmas decorations and lively tunes. This professionally chip-timed race is all about coming together with your loved ones to run or stroll along a picturesque lakeside course, surrounded by the most heartwarming Christmas energy.
You’ll be glowing brighter than Rudolph’s nose thanks to the awesome complimentary glow products you’ll get with your registration! Lace-up those sneakers and come create cherished memories while celebrating the true spirit of Christmas at one of the most anticipated events of the year. And if you work up a post-run appetite, be sure to explore the wide variety of restaurants and local Sarasota breweries in the area!
Plan Your Next Visit!
Are you ready to explore the variety of holiday-themed things to do in Siesta Key Florida this year? Browse our selection of stunning rentals and start planning your adventure today!
Book Your Siesta Key Vacation Rental
Discover the perfect Siesta Key vacation rental with The Cottages on the Key.
When it comes to vacationing on the #1 ranked beach in the United States, Siesta Key, Florida, our rentals are your ticket to a successful and memorable getaway. Whether you’re jetting off with friends or embarking on a family adventure, our Siesta Key rentals are the ultimate choice. Dive into a selection of luxurious homes, each promising fantastic amenities and convenient access to the breathtaking Siesta Key beaches.
If you’re planning a grand group escape, our 5-bedroom Siesta Key house rentals will be your dream come true, accommodating up to a whopping 24 guests! Perfect for family reunions, weddings, birthdays, or any celebratory gathering, these spacious havens offer not only ample room but also a treasure trove of top-notch amenities, all within a stone’s throw of the area’s top attractions.
And for those who crave the ultimate in luxury, our collection of Sarasota vacation rental homes awaits. With private pools, hot tubs, lush tropical landscaping, waterfront vistas, canal access, kayaks, private carports, and sizzling gas grills. Don’t let this opportunity slip through your fingers! Book your Siesta Key vacation rental today and prepare for an adventure like no other. Your slice of paradise is just a reservation away.