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Check Out the Annual Christmas Parade in Anna Maria Island

Anna Maria Island is a great place to spend the holidays. As many try to escape the drudgery of winter in other parts of the world, it can be a great opportunity to come to Florida to experience the warmer weather.

Even with the warmer weather, however, there are still plenty of opportunities for you and your family to enjoy the festive season with the many different holiday-oriented events happening on the island, including the annual Anna Maria Island Privateers Christmas Parade near our Anna Maria Island, FL rentals.


The Anna Maria Island Privateers Christmas Parade is a great way to get into the holiday spirit. The event typically takes place in early December on a weekend morning, and exact dates and times will be available closer to the event. A parade is a free event that is full of various floats. From the famous “skullywag” float to the annual Santa Clause themed floats, there is plenty to keep your kids entertained at the parade. 


If you are looking to follow the parade for a distance, it is a great way to see the surrounding area. The float spans the length of the island, starting all the way from Bay Front Park and ending at Coquina Beach. So even while you are taking in the parade, there are plenty of other sites and attractions to experience. The parade is free for all those who attend, and there will be plenty of snacks, hotdogs, and soda to keep you and your kids happy while attending the parade.

Santa on Christmas Parade in Anna Maria Island

Looking for other events to partake in after the parade? There is the annual Winterfest Fine Arts and Crafts Festival. With a ton of vendors and craft makers at the event, it is a prime destination to get some last-minute Christmas shopping completed. There is also a wide range of local history and environmental information presented at the festival. This history includes learning about the rare wildlife that inhabits the area, as well as the natural preserves that exist. To end out the festival, there is a raffle held where people can win items and crafts that are strictly unique to the area of Anna Maria Island. Funds from the raffle go to supporting various wildlife and historical initiatives that take place on the island.

Places to Stay

There are many great Anna Maria Island house rentals to stay in during your winter vacation. Even though Anna Maria Island hovers around 70 degrees, it is still a great time of year to spend time outside and enjoy the sunshine.

The Coconut Bayou is a rental unit available to house six people with three bedrooms and three bathrooms. It’s also a dog-friendly stay! At the North End of Anna Maria Island, the Coconut Bayou is located near many restaurants and fun places to shop. The Coconut Bayou is also close to many beaches and is a nice and quiet neighborhood. It is a great intimate getaway location if you are looking to relax. The unit comes with regular five-star reviews from guests who stay there. Rest assured, you can feel good staying at the Coconut Bayou. 

View of the pool at The Idle House || Florida Dreams Realty

The Idle House is a four-bedroom and four bathroom luxury house available in Anna Maria Island. With all brand-new amenities and a ranch-like aesthetic, The Idle House is a luxurious getaway. Looking to participate in some of the best golf courses during your stay? Then the Idle House is the best Holmes Beach rental to stay due to its proximity to them. It’s also close to bays and canal fronts, making it an ideal spot to participate in some great boating endeavors. 

View of the pool at the Sailors Dream || Florida Dreams Realty

The Sailors Dream is a three-bedroom and three-bathroom home, an idyllic stay for a small group of travelers. If you are looking to do some fishing or snorkeling, it is a great place to tune out the world and to enjoy the ocean. With a waterfront view and near to the oceanside, it is a great spot to lounge, catch some rays and some waves. For more information on all of our rentals, contact us today!