Celebrate the Holidays in Siesta Key, Florida
Dreaming of a white Christmas made of sand instead of snow? Siesta Key, Florida, transforms into a tropical winter wonderland each holiday season. With twinkling lights, beachside events, and plenty of Santa sightings, this island offers the perfect mix of festive cheer and coastal charm.
Whether you’re staying for a weekend getaway or an extended holiday vacation, here are the top Christmas events in Siesta Key for 2025 that you won’t want to miss!
1. Meet Santa Claus at the Siesta Key Chamber of Commerce & Visitor Center
5223 Avenida Navarra, Siesta Key, FL
2-4pm, November 29, 2025
Give the jolly fellow a proper Siesta Key welcome at the Meet Santa event, hosted by the Siesta Key Chamber of Commerce & Visitor Center. Bring the kids, snap photos with Santa, and kick off the season with island-style holiday spirit.
If you’re visiting for Thanksgiving week or planning a longer stay, this event is a cheerful way to ease into December—and don’t forget to bring your Christmas list!
Pro Tip: Stop by nearby shops and cafés along Avenida Navarra for a post-photo treat or some last-minute gift shopping.
Meet Santa Claus at the Siesta Key Chamber of Commerce to kick off the holiday season on November 30, 2025.
2. Siesta Key Light Up the Village + Holiday Parade
Siesta Key Village
5:30 PM – 9:00 PM EST, November 29 , 2025
When the lights twinkle on, Siesta Key officially rings in the holiday season! The Light Up the Village and Holiday Parade is one of the island’s most beloved annual traditions.
Siesta Key Village transforms overnight into a beachside Christmas wonderland filled with music, festive decorations, and community spirit. Line up along Beach Road or Ocean Boulevard for the best views of the parade featuring local floats, marching bands, and even Santa himself.
After the parade, join the countdown for the town’s Christmas tree lighting and enjoy holiday cheer throughout the night.
Santa stands aboard a festively decorated boat float, waving to the crowd as colorful lights illuminate the Siesta Key Holiday Parade.
3. Sandy Claws Beach Run
948 Beach Road, Sarasota, FL
Sat December 13, 2025
Trade snow for sand and sneakers for Santa hats! The Sandy Claws Beach Run has been a Siesta Key holiday tradition for nearly 50 years.
Runners of all ages can participate in this 5K or 1-mile fun run along the world-famous Siesta Beach. Expect scenic Gulf views, ocean breezes, and plenty of holiday-themed costumes. Santa himself cheers participants across the finish line!
Whether you run, walk, or just cheer from the sidelines, it’s one of the most spirited ways to start your Christmas countdown.
Join hundreds of runners on Siesta Beach for the 49th Annual Sandy Claws Beach Run this December.
4. Christmas Boat Parade of Lights
5 Bayfront Dr, Sarasota, FL
December 13, 2025
Set sail into the season at the Christmas Boat Parade of Lights, one of the most dazzling holiday spectacles in Sarasota Bay.
Watch as boats of all sizes glide across the water, decked out with glowing lights, festive decorations, and plenty of Santas at the helm. The best viewing spots are at Marina Jack restaurant in Downtown Sarasota or Bayfront Park.
It’s a breathtaking sight as reflections of holiday lights dance across the bay—perfect for a romantic evening or a family night out.
Watch Sarasota Bay light up with festive boats during the annual Christmas Boat Parade of Lights.
5. Lights in Bloom at Marie Selby Botanical Gardens
1534 Mound St, Sarasota, FL
December 6, 2025 – January 3, 2025
Experience over two million lights illuminating the lush tropical gardens of Marie Selby Botanical Gardens. Voted one of USA Today’s Best Botanical Garden Holiday Lights, Lights in Bloom is a must-see attraction for anyone spending Christmas in Siesta Key.
Stroll through pathways lined with glowing orchids, radiant palm trees, and larger-than-life light sculptures. It’s a breathtaking fusion of nature and artistry that dazzles guests of all ages.
Colorful lights illuminate tropical plants and their reflections on the water during the Marie Selby Botanical Gardens Holiday Light Show near Siesta Key.
Celebrate the Holidays with Gertrude Rentals
Make your holiday getaway unforgettable with a stay at Gertrude Rentals. Choose from stylish steps from the beach condos and spacious family homes, many within walking distance of Siesta Key Village, restaurants, and parade routes.
Whether you’re escaping the cold or starting a new holiday tradition, Siesta Key offers the perfect mix of sunshine, sand, and Santa this Christmas season.
👉 Book your stay now at GertrudeRentals.com
