Spend your holiday season on Anna Maria Island! With a variety of exciting holiday events happening throughout the month, there’s something for the entire family to enjoy during this magical time of year. After the challenges brought by Hurricane Helene and Hurricane Milton, our island has come together, with many local businesses reopening and thriving once again. These heartwarming community events are sure to create unforgettable memories for you and your loved ones!

Holmes Beach Christmas Tree Lighting

Date: Dec 6, 2024

Time: 5:45 PM

Location: Hancock/Whitney Bank, across from the Chamber parking lot, Holmes Beach

Features: Annual Christmas tree lighting ceremony to kick off the holiday season

Christmas on Bridge Street

Date: Dec 7, 2024

Time: 2:00 PM

Location: Bridge Street, Bradenton Beach, Anna Maria Island

Features: Transforming into a magical winter wonderland with the island’s largest light display, streetlights, palm trees, storefronts, and clock towers adorned in twinkling lights. A stunning 40-foot Christmas tree at the center of town. A celebration of the city’s restoration of Bridge Street, honoring the spirit and strength of Bradenton Beach. Food, drinks, music, and additional festive activities.

Bradenton Beach Restaurant Crawl for Recovery

Date: Dec 7, 2024

Time: 3:00 PM – 7:00 PM

Location: Bradenton Beach

Features: $15 admission. Enjoy food and drinks while supporting local restaurants recovering from Hurricane Helene and Milton.

Lester Family Fun Day

Date: Dec 7, 2024

Time: 10:30 AM – 2:00 PM

Location: The Center of Anna Maria Island, 407 Magnolia Avenue, Anna Maria, FL 34216

Free Admission

Features: Pony rides, face painting, crafts, fun inflatables, MHS drumline performance, burgers, and hot dogs. Santa arrives at noon.

Christmas in the Garden 2024

Date: Dec 1 – Dec 31, 2024

Time: 5:00 PM – 9:00 PM (Special performances at 6:00 PM)

Location: Longboat Island Chapel, 6200 Gulf of Mexico Drive, Longboat Key, FL 34228

Features: Celebration of lights and music

Winter Wonderland 2024

Date: Dec 14, 2024

Time: 5:00 PM – 8:30 PM

Location: Old Main St., Bradenton, FL 34205 (Less than 30 minutes from Anna Maria Island)

Features: Meet Santa and capture holiday memories. Photo opportunities with festive vignettes. Lively performances by local youth groups. Winter carnival with games like snowball toss and ice fishing. Make-and-take creative activities. Snowfall magic. Local vendors with gifts and seasonal treats.

Shore Thing Tiki Cruises with Santa

Date: Dec 14, 2024

Times: 9:30 AM – 10:30 AM & 11:00 AM – 12:00 PM

Date: Dec 19, 2024

Time: 12:30 PM – 1:30 PM

Date: Dec 21, 2024

Times: 9:30 AM – 10:30 AM & 11:00 AM – 12:00 PM

Location: 119 Bridge St Suite 140, Bradenton Beach, FL 34217

Features: Cruise the beautiful waters of Anna Maria Island with Santa.

Manatee River Holiday Boat Parade

Date: Saturday, Dec 14, 2024

Time: Evening (specific time not mentioned)

Location: Manatee River

Features: Annual tradition with boats of all sizes decorated for the holidays, competing for prizes and the winning title. A nonprofit charity event celebrating community traditions, local businesses, and holiday spirit.

Holiday Celebration on Anna Maria Island

Date: Dec 14 and Dec 21, 2024

Time: 11:00 AM – 5:00 PM

Location: Gulf Dr., Pine Ave., and South Bay Blvd., City of Anna Maria

Features: Display of beautifully decorated tree ornaments. Santa Claus appearance (Meet Santa from 1:00 PM to 3:00 PM on both days).

Bradenton Gulf Islands Concert Series 2024-2025

2024-2025 lineup:

Dec 14, 2024: Sheena Easton

January 11, 2025: The Wailers (outdoor lawn performance)

February 8, 2025: Robby Krieger of The Doors

March 24, 2025: The Moody Blues’ John Lodge

Location: The Center of Anna Maria Island, 407 Magnolia Avenue, Anna Maria, FL 34216

Book Your Stay with Us!

We know how important it is to find the perfect rental home for the holidays, and there’s no better place to spend this special time than with your loved ones on the beautiful Anna Maria Island. Whether you’re looking for a cozy beachfront retreat, a dog-friendly home, or a rental with a private pool, we have a variety of options to suit your needs. Let us take the stress out of your planning and ensure your stay is seamless and unforgettable.

Call us today and speak with one of our Vacation Rental Specialists who will guide you through every step, from booking to check-out!

Reservations: (941) 778-6066 x1