Siesta Key Upcoming Events for the Christmas Holiday Season

A Siesta Key vacation is a unique way to spend the Christmas season. With the warmer climate, Siesta Key offers a wider variety of holiday events.

With so much to do and see a short jaunt from vacation homes on Siesta Key, you should try to check out at least a couple of the events happening in late November and throughout December. To make your holiday planning a little easier, we’ve listed some of our favorite events happening on Siesta Key and in the surrounding areas here.


Siesta Key and the surrounding area is home to some incredible holiday events that you’ll want to take advantage of. Namely, Sarasota is just minutes away and hosts some of the biggest events around. On December 5th, visit the Circus Museum at the Ringling for Holiday Splendor, where you will enjoy extended evening hours and will experience holiday music performed by local school students. Bring an unwrapped toy to support the U.S. Marine Corps Reserve Toys for Tots and receive free admission!

On December 14th, visit Westfield Siesta Key in Sarasota for SantaFest and Holiday Gift Market. There will be tons of family-friendly activities like face painting, gift raffles, and of course, getting to meet Jolly Old Saint Nick himself! This is the perfect way for you to spend time with your family, get some holiday shopping done, and find a special souvenir. The Gift Market takes place from noon until 6 p.m., and SantaFest is from 3 p.m. until 6 pm.

You don’t even have to leave Siesta Key to experience the Light Up the Key Holiday Parade and Holiday Open House, a special celebration that guests young and old will cherish. Meet with Santa and his elves, get some holiday treats, and receive a gift bag if your child is one of the first 250 children to arrive! This event will take place in Siesta Key Village from 6 p.m. until 9 p.m. on Saturday, November 30th.

Additional Details

Siesta Key Light Up the Village Parade and Holiday Open House

When: Saturday, November 25, 2017
Where: 5238 Ocean Blvd., Siesta Key, FL

The Light Up the Village Parade takes place at Siesta Key Village right on Ocean Boulevard and is a perfect event for the entire family.

Children will have the opportunity to give their Christmas wish lists to the man in red himself. There’s also face painting and a visit with Santa’s elves.

The main event is Santa’s arrival on a fire truck around 6:15 p.m. to greet all the children who have come to see him. The first 250 children in line to meet Santa will receive special gift bags.

Organized by the Siesta Key Chamber, this is one of the best family-friendly holiday events offered this season. It runs from 6 to 9 p.m.

Sarasota Downtown Holiday Parade

When: Saturday, December 2, 2017
Where: Along Main St. from Washington Blvd.

Running for more than two decades, the Sarasota Downtown Holiday Parade is one of the events that locals in the area look forward to every year. This event truly marks the beginning of the Christmas season in Sarasota.

With a different theme every year, this parade continues to be a crowd pleaser among the thousands of participants in the procession and many more viewers.

You’ll see marchers, walkers, floats, cars, motorcycles, trucks, clowns, and more. There are prizes for the best floats that grace the streets – the first prize float will win the mayor’s trophy.

The parade starts at 7 p.m. and lasts about two hours. It has become one of the biggest and most well-known parades in Florida. Main Street is blocked off to traffic during the event, which draws nearly 25,000 +spectators. If there is one Christmas event you don’t want to miss, this is it.

sarasota boat parade

Sarasota Holiday Boat Parade of Lights

When: Saturday, December 9, 2017
Where: 2 Marina Plaza, Sarasota, FL

At 6:00 pm, the Christmas Parade takes to the waters as boats of all sorts grace the waters around Marina Jack. There are three different dining options with live performances from local bands, and the option to have a drink at the Piano Bar. Lunch or dinner cruises on the water will be available.

A variety of holiday-themed floats and boats will be in the parade – a fun and unique way to kick off the Christmas season.

If you’d rather stay on the shore, sit back, relax, and watch the decorated boats go by as the sun sets in Sarasota. Marina Jack Restaurant and Bay Front Park are among the best spots to watch the procession.

Lights in Bloom

When: December 14 – January 4
Where: 900 S. Palm Ave., Sarasota, FL

Sarasota’s Marie Selby Botanical Gardens lights up over Christmas week this year for their special holiday event, Lights in Bloom. From 6 – 9 p.m. each night, thousands of lights adorning the trees, bushes, flowers, and other garden fixtures will be flicked on for a magical Christmas experience.

Walk through the garden as the walkways are transformed into sensory light tunnels. Flowers, butterflies, and dragonflies come alive under the lights for this tropical holiday paradise.

The event is so magical that even Santa and his elves come to check it out every night and even meet with children to hear their Christmas wishes. There’s also children’s games, activities, food, and live entertainment.

Book Your Siesta Key Vacation Rental

These are just a few of the many upcoming holiday traditions in the area that are well worth making a stop at during your stay at our vacation homes on Siesta Key!

What is the Weather Like?

The great thing about visiting Siesta Key in the winter is that you won’t have to bundle up quite as much as you would in other destinations. In December, high temperatures are in the low-to-mid 70s, and lows hover around 50 degrees. The water may be a little chilly, but you can definitely still take a dip in the pool or the Gulf, as well as enjoy all of the other fun outdoor activities near our Siesta Key vacation homes.

What to Pack

When you’re planning for a beach vacation in the winter, it can be hard to know what to pack. Go ahead and break out the shorts and t-shirts, but you’ll want to pack at least one pair of pants and a jacket for the cooler days.

One thing that you won’t have to worry about packing is towels, as our Professional Linen Program has you covered. We will provide all of your bath and beach towels, washcloths, and bedsheets, leaving you extra room in your suitcase to bring home the perfect souvenir!

Where to Stay

We are proud to be the premier destination for Siesta Key vacation rental homes. Our rentals will suit parties large and small, and you will always feel right at home in our luxurious accommodations. Enjoy amenities like laundry facilities, full kitchens, covered deck, and HDTVs throughout your home. Step outside for an incredible view of the Gulf or to have a relaxing barbecue with your family. All of our rentals are also conveniently located near the beach and Siesta Key Village, so you’re never far from fun!

Visiting Siesta Key during the holidays will give you and your family unforgettable memories everywhere you turn. You may never go back to celebrating the season at home! For more information about Siesta Key in the winter, as well as our full range of rentals, contact us today!


Siesta Key Luxury Rental Properties
5111 Ocean Blvd. Suite B, C & D
Siesta Key, Florida USA 34242
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