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Top Winter Events in the Florida Keys

There really is a lot to do in Florida during the winter months, and if you are not familiar with the area, you may miss out on something exciting! Fortunately, your choice of making Florida your winter getaway wasn’t the only intelligent one you made this year; you also picked RentTheKeys for your vacation escape! If you don’t have a great time while you are staying in one of our fabulous properties, we consider it a failure on our part, and as such, we have created this guide to the top Florida winter events near your vacation sanctuary to ensure that every minute of your stay is the most exciting one you have ever enjoyed!

See the Lights With These Florida Winter Events

Even without cold breezes and snowy landscape, Christmas is still a beautiful holiday in the Keys, and there will be plenty of opportunities to view tree lighting festivities during your stay! Sarasota’s Downtown Christmas Tree Lighting takes place on December 2 from 6 to 8 PM at Selby Five Points Park and offers music, treats, and photo opps with the jolly old elf himself! Holiday Night at St. Armand’s Circle is held on December 3rd from 6-9 PM, featuring an elegant celebration of the season that begins with a Christmas Carol singalong, offers photos with Santa, and the opportunity to do some last minute shopping in the stores that make this circle special! For Christmas Lights shows with a specific Florida twist, the Sarasota Christmas Boat Parade of Lights held December 11th and the Manatee River Holiday Boat Parade in Bradenton, also held on December 11th allow you to watch a parade of boats decorated in their holiday finest.

Annual Christmas Parade, December 4, DeSoto Square Mall in Bradenton

Everyone loves a parade, and the annual Christmas Parade in Bradenton sponsored by the Sarasota Jeep Club offers yet another twist to the standard parade; this one consists of Jeeps old and new decorated to reflect the season! Starting at 5:30, just before the sun sets, and ending at 8:30, this local event isn’t one of our fanciest, but it is definitely a lot of fun.

Sarasota Seafood & Music Festival, January 14-16, JD Hamel Park

If a celebration of seafood and music sounds like a perfect way to start out the new year, this exciting festival in Sarasota is one of our favorites, offering expertly prepared seafood dishes that will make you miss Florida when you have to return home, refreshing beverages of both the alcoholic and non-alcoholic varieties, and all the music your ears love to hear! Tap your tones to the sultry sound of jazz music, rock hard with our local rock bands, and get your funk on with Caribbean music, all under the open skies of Sarasota. The Humane Society will be bringing along a few of their friends who will be up for adoption at these Florida Keys winter events, and even though it isn’t likely you will be able to bring a new friend home with you, being able to pet and cuddle the furry babies will bring a smile to your heart!

Lido Beach Winter Fine Art Festival, February 5 & 6, Lido Beach Pavilion

Lido Beach is one of the area’s most beautiful beaches, but it pales in comparison to the beauty of the art shown at the Lido Beach Winter Fine Art Festival! Offering the best of the best, this juried show never fails to please, and as you stroll the aisles examining oil paintings and elegant sculptures, watercolors that show off the delicate beauty of a beach landscape, and a variety of other genres, you will find yourself marveling that as you are surrounded by all this beauty, you are also comfortable, warm, and the sun is shining! Winter in Florida is really just a continuation of summer, and who is going to complain about that?

Sarasota Winter Craft Show, February 26 & 27 at JD Hamel Park

Have you ever noticed that the more scenic places tend to attract the most talented artists? Maybe the beautiful scenery just makes it easy for talented people to create masterpieces, or maybe we just get lucky, but right here in the Sarasota area, the masterpieces that are being created are out of this world and the Sarasota Winter Crafts show allows you the opportunity to take a part of Florida home with you! Offering art pieces of all genres, you will want to bring everything you see home with you from these Florida Keys winter events, but even if your suitcase isn’t large enough for that painting of the sailboats on Anna Maria Island, the hand-crafted jewelry is small enough to fit in your purse, luggage, or to be worn home, impressing everyone on your plane!

Choose RentTheKeys

However you spend your winter days in Florida, spending your evenings in our comfortable and luxurious vacation escapes will be the highlight of your getaway. Reserve your favorite today!