By the time you read this, your holidays for 2024 will have concluded and your resolutions for 2025 may include one that promises more beach days in your future, with a trip to Anna Maria Island over the holidays found at the top of your wish list. For us, 2024 wasn’t the greatest of years, but as we at Anna Maria Life Vacation Rentals roll up our sleeves and get to work making sure that every property we offer for your vacation accommodations shines bright, we are excited about all the possibilities of 2025. So much so, we decided to sit down and create this Anna Maria Island holiday preview, spreading our excitement to those who are already making plans for the next major holidays on the calendar!
Memorial Day Weekend
The best way to pay homage to those we lost is by continuing to live your best life, and Memorial Day Weekend on the island will make you feel glad to be an American. Spending your days frolicking in the surf and relaxing on white sand beaches and your evenings celebrating the culinary landscape with visits to Beach Bistro, located at 6600 Gulf Drive. An annual observance at City Pier Park starts at 10 AM, leaving you plenty time after to explore all the island has to offer. Memorial Day is held on May 26 in 2025.
Labor Day Weekend
Don’t you just love a holiday that doesn’t just acknowledge how hard you work, but also gives you paid time off for more relaxation? Labor Day Weekend on Anna Maria Island is an idyllic experience, one that includes plenty of beach time, delicious sweet and fresh seafood, and hopefully more than a few rum punches that will serve as exclamation points to the end of summer. Labor Day falls on September 1 in 2025.

Halloween
As you begin to get out the sweaters and boots for your little trick or treaters, we on AMI are still luxuriating in summer, but that doesn’t mean we won’t celebrate the spooky season. Our Trail of Treats, held on Halloween offers trick or treating at local businesses and a costume contest at the end of the night and for the adults, or children who don’t frighten easily, Sarasota Suncoast Tours offers their Stories, Shipwrecks, and Spirits on Anna Maria Island Ghost tour that takes participants to where the spirits are known to linger.
Thanksgiving
Some years it is easier to feel thankful than others and in 2025 when your Florida vacation on AMI will give you a long list to of things to be thankful for, including warm weather, beach days, and a delicious Thanksgiving feast at Pier 22, located at 1200 1st Avenue West. Our favorite part of Thanksgiving, aside from the meal, is waking up early on Thanksgiving day and watching the Macy’s Thanksgiving Day parade in our jammies and if you feel the same, the state of the art televisions in our Anna Maria Life Vacation Rentals holiday hideaways will make you feel as if you are on the streets of New York watching the parade live and in person; only you will be warm, cozy, and preparing for a walk along sandy shores after the parade!
Christmas
From the lighting of the Christmas tree on Pine Avenue, to meet and greets with Santa Claus, the holidays shine bright on Anna Maria Island every year and it truly is the most wonderful time of the year. The Holiday of Treasures event that takes place on Bridge Street in Bradenton Beach helps us cross off all the names on our holiday gift lists and offers more chances to meet the Claus’s, as Mrs. Santa joins in the fun as well. And last but not least, in the middle of December brings the Privateers Christmas Parade, a festive procession of floats, marching bands, local celebs, and for a whimsical twist, the Privateer’s most famous pirate ship sails majestically down the boulevard! Christmas on Anna Maria Island in 2025 is destined to be the holiday you compare all others against from here on out.

New Year’s Eve
And with a blink of an eye, we arrive at the end of 2025, filled with joy, happiness, and hope that 2026 will be just as spectacular as 2025 was and if you are spending the last day of the year on Anna Maria Island, we are pretty sure it will be. Watching fireworks from the balcony of your Anna Maria Life Vacation Rentals is always a great idea, but if you want to get out and celebrate, both nearby towns of Bradenton and Sarasota offer a family friendly celebration in their downtown areas.
Celebrate the Anna Maria Island Holidays of 2025 with Us
Offering a soft place to land at the end of every celebration, our Anna Maria Island rentals will be where your most treasured memories are created. Reserve your favorite escape today!