Why Choose Anna Maria Island for Labor Day Weekend

Labor Day weekend traditionally marks the unofficial end of summer, so why not enjoy the last few days of summer fun on Anna Maria Island? With its wide, white sandy beaches and charming old-school Florida atmosphere, it’s the perfect place to kick back, relax, and enjoy a slower pace of life. 

Where to Stay

If you’re looking for a place to stay during Labor Day weekend, look no further. Our Anna Maria Island and Bradenton Vacation Rentals have everything you need to make your stay memorable. Whether you’re looking for a private pool to soak up the sun, beautiful beach views, or even a hot tub to stargaze, we have just the getaway for you. 

Beachfront

The beaches here are truly the shining star, so make your stay as close to them as possible. Forget packing the car for a beach day; simply step out your door and onto the sand. 

Private Pool

If your perfect summer send-off involves sun-drenched days by the pool, we have the ideal accommodations for your Labor Day Weekend getaway. Choose from our diverse selection of Anna Maria homes, including options with private pools, for a truly relaxing stay.

Lake View

Discover unparalleled beauty with our Lake View properties. Imagine ending your day captivated by stunning sunsets, observing local wildlife, or simply unwinding in the comfort of your own home – all without ever having to leave. If breathtaking views are what you seek, our Lake View properties are the perfect choice.

Golf Course

If your ideal Labor Day weekend involves golf, consider booking one of our rentals with the golf course filter. You’ll be just steps away from the tees!

Hot Tub

Escape to a private hot tub this Labor Day for a revitalizing getaway. Find your perfect sanctuary by selecting the “Hot Tub” amenity. Create lasting memories and indulge in comfort, privacy, and natural beauty.

We have the perfect house for your Labor Day weekend getaway, no matter how you choose to spend it. Browse our rentals by amenity and ensure your trip is unforgettable!

Labor Day Activities

During this time of year, there are a number of fun-filled activities to enjoy during your stay! Whether it’s a classic beach day or snorkeling the local reefs, our rentals put you in the heart of it all. 

Snorkeling

Make your beach day more exciting with snorkeling! Bradenton Beach is ideal this time of year due to its calm, shallow waters, perfect for all ages. For an added thrill, venture about 200 yards offshore to explore an artificial reef teeming with diverse marine life. Find more details on snorkeling locations and gear rentals in our blog.

Fishing charters

Fishing charters are another great way to see the local wildlife and experience the beaches and waters. Charters can range from anywhere between $300-$700, depending on the time of year and experience you are looking for. If you’re looking for a family-friendly tour, we suggest going through AMI Escapes. This 3-hour tour is made with families in mind and emphasizes entertainment just as much as fishing. 

Sunset cruises

Another great way to experience all the island has to offer is to take a sunset cruise around the gulf. Here you will not only get to experience breathtaking sunsets, but also wildlife encounters, tranquil waters, and beautiful scenery. 

Beach day

A visit to Anna Maria Island isn’t complete without a beach day! Make the most of the last days of summer by swimming, building sandcastles, and enjoying the sun. Coquina Beach is an excellent choice for Labor Day weekend, offering convenient amenities like public restrooms, showers, and ample free parking, making it perfect for families during a busy holiday.

Where to Eat & Drink

Dining out during holiday weekends can be a challenge, but we’ve compiled a list of essential eateries that will help you navigate the crowds and enjoy delicious meals.

Ginny’s & Jane E’s Café

This beloved joint is an Anna Maria staple. Open daily till 3, they offer a variety of breakfast and lunch options. We suggest trying the legendary oversized cinnamon roll!

The Waterfront Restaurant

This premier sit-down restaurant is a must-have when visiting. We suggest trying the shrimp and grits for a truly local experience. While they are open on holiday weekends, reservations are required. 

Floridays Woodfire Grill & Bar

Searching for a celebratory drink by the water? Floridays offers tropical margaritas perfectly paired with their crab cakes. Enjoy waterfront views during happy hour, or for a late-night dinner and drink, they are open until 10 PM.

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4th of July on the beach on Anna Maria Island

4th of July on Anna Maria Island

As summer reaches its peak on the Florida Gulf Coast, there’s no better place to be than Anna Maria Island. If you’re looking for a fun destination to spend the July 4th holiday, Anna Maria Island is it. This island paradise offers laid-back charm, pristine beaches, and vibrant Independence Day celebrations that make it the perfect destination for a memorable 4th of July getaway.

Anna Maria Island is a coastal gem known for its Old Florida vibe, stunning beaches, and pristine natural beauty. With all of this on one 7-mile island, it’s no wonder visitors flock to this gorgeous destination year-round. Whether you’re seeking relaxation on the sugar-white sands, exploring the island’s charming boutiques and art galleries, or indulging in fresh seafood at local restaurants, Anna Maria Island offers something for everyone.

What is Anna Maria Island Like in July?

Sunny day on Holmes Beach, Florida

July on Anna Maria Island typically brings warm weather in the 90s (F) and plenty of sunshine, making it the perfect time to hit the beach and enjoy outdoor activities. During summer in Florida, it’s essential to prepare for the possibility of afternoon showers, so bring sunscreen, an umbrella, and lightweight clothing to stay comfortable throughout your stay. 

As one of Florida’s most popular tourist destinations, Anna Maria Island can experience increased crowds during summer, especially around the 4th of July holiday. Booking accommodations and making dining reservations in advance is recommended to ensure a seamless and enjoyable experience during your visit.

4th of July Events on Anna Maria Island

Anna Maria Island is full of patriotic spirit and during the 4th of July. Here are the Independence Day events you won’t want to miss while visiting Anna Maria and nearby Bradenton over the 4th.

  • Independence Day Parades. The Anna Maria Island Privateers 4th of July Parade is a high-spirited romp where the local pirate crew navigates the island in their galleon, tossing beads and candy to spectators. On nearby Longboat Key, the “Shortest Parade in America” takes place on July 4th, starting from Centennial Park and includes pet costume contests and live music.
  • 4th of July Picnic Celebration. At the end of the Privateers’ parade route, head to City Pier Park for a picnic celebration. Enjoy food and live entertainment for the whole family, as well as kids’ activities, starting at noon.
  • Independence Day Fireworks. On July 4, head to Bradenton to catch a spectacular fireworks display over the Manatee River in downtown Bradenton. The Bradenton Riverwalk is a great place to set up your chairs or blanket, with 2 miles of paved paths, as well as an amphitheater and playground. The fireworks should also be visible from Anna Maria Island, with the best spot being close to Anna Maria City Pier.

Things to Do on Anna Maria Island

Birds on the beach in Anna Maria Island

Enjoy the beaches. Spend your days soaking up the sun on the island’s sugar-white sands, swimming in the clear turquoise waters, or simply unwinding with a good book beneath the shade of an umbrella. Holmes Beach is the lively hub at the center of the island, while Bean Point Beach on the northern tip and Coquina Beach on the southern end are quieter, offering a peaceful spot to catch a spectacular sunset.

Explore nature. In addition to pristine beaches, Anna Maria Island has abundant natural beauty waiting for you to explore. Nature lovers will delight in the island’s diverse ecosystems, from hiking through the mangrove forest in Leffis Key Preserve to exploring the surrounding waterways. Rent a kayak or paddleboard and embark on a paddling adventure through the nearby nature preserves and bays, where you can spot dolphins, shorebirds, and maybe even a manatee. To experience the island’s nature with a guide, book a dolphin watching tour, embark on a snorkeling adventure or head out on a fishing charter.

Explore the island. Anna Maria Island is brimming with charm and character, with local shops and restaurants creating a quirky atmosphere unique to the island. Head to Pine Avenue in Anna Maria to visit the historic Anna Maria City Pier and learn about the island’s past at the Anna Maria Island Historical Society. Bridge Street in Bradenton Beach is a vibrant 3-block stretch of restaurants where you can immerse yourself in the lively energy of the island. Since Anna Maria Island is fairly compact, renting a bicycle or golf cart is a great way to explore. Walking and catching a ride on the free trolley is also a fun way to get around.

Plan Your Visit

Vacation rental on anna maria islandWhether you’re soaking up the sun, exploring the island, or marveling at the fireworks show, Anna Maria Island invites you to celebrate Independence Day in patriotic style.

Ready to experience the magic of Anna Maria Island this 4th of July? Book an Anna Maria Island or Bradenton beach vacation rental through Island Dreams, and plan the perfect summer getaway. We offer nearly 60 professionally managed homes and condos, fully equipped with everything you need for a memorable stay.

Accommodations can fill up fast, so book your vacation rental early and start planning your unforgettable 4th of July getaway!

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Christmas Anna Maria Island

Celebrate an Anna Maria Island Christmas

The holiday season is right around the corner, and if you’re looking to give the gift of incredible memories and a trip of a lifetime, consider a stay with Island Dreams Realty on Anna Maria Island. Our Anna Maria Island vacation rentals provide the perfect backdrop for your holiday festivities. Stop by one of the many holiday events on Anna Maria Island and Bradenton during your stay and get into the holiday spirit!

December on Anna Maria Island

The weather on Anna Maria Island in December is dreamy. Highs reach the 70s, and lows average around the 50s, making the temperatures perfect for outdoor activities. Many people flock to the area during December to escape the cold up north, so if you’re looking for a warm vacation destination in December, Anna Maria Island is the place for you. 

Holiday Events on Anna Maria Island & Bradenton

Winter Wonderland Bradenton

Photo from Realize Bradenton

A Night Before Christmas at G.T. Bray Park – Dec. 7, 2024

Kick off the holiday season with A Night Before Christmas at G.T. Bray Park in Bradenton. From 4 PM – 8 PM, kids can enjoy inflatables, face painting, a petting zoo, crafts, a foam zone, and a snow slide. Snap photos with Santa and Mrs. Claus while Christmas carolers sing holiday favorites. There will also be food vendors and a “Shop Local” market where you can find the perfect Christmas presents for loved ones. “The event is free, but a suggested donation of a new, unwrapped toy is recommended. 

Lester Family Fun Day – Dec. 7, 2024 

The 22nd Annual Lester Family Fun Day is a celebration of all things Christmas! From 10:30 AM – 2 PM, children can participate in crafts, pony rides, face painting, and fun inflatables. There will also be a drumline! Santa will appear at noon, so make sure your cameras are ready! Admission is free and the event takes place at the Center of Anna Maria Island. 

Christmas in the Garden – December 1 – 31, 2024

Throughout the month of December, at Longboat Island Chapel in Longboat Key, you and your loved ones can enjoy an evening of Christmas lights and music from a number of musicians. Performances will take place from 5 PM – 9 PM, and admission is free. There is limited seating, so be sure to plan accordingly. For a list of dates, visit here. 

Manatee River Holiday Boat Parade – December 14, 2024

The Manatee River Holiday Boat Parade is a favorite holiday tradition for many in the area. A fleet of boats decked out in holiday lights will stroll along the Manatee River. The parade will start at sundown, and the public can view the boats from the Green Bridge and the Palmetto Pier.

An Old Florida Christmas – December 14, 2024

Celebrate the holidays in Bradenton at An Old Florida Christmas. This annual event features artisan vendors, food trucks, activities and crafts, and live music. From 10 AM  – 3 PM, shop homemade gifts, treats, and more while listening to festive holiday music.  

Winter Wonderland Downtown Bradenton – December 14, 2024

Keep the holiday fun going after visiting An Old Florida Christmas and stop by Winter Wonderland in Downtown Bradenton. Old Main Street will undergo a magical transformation from 5 PM – 8:30 PM with snow falling and plenty of winter-themed activities. Take a ride on the snow slide, snap pictures with Santa and Mrs. Claus, and watch live performances from local youth groups. There will be a winter carnival with exciting games like snowball toss and ice fishing, and local vendors will be set up where you can shop for unique holiday gifts, food, and drinks.

Why Spend Christmas on Anna Maria Island and Bradenton?

Anna Maria Island vacation rental

Take a break from the cold and snowy weather and escape to Anna Maria Island and Bradenton for a warm, sun-filled holiday getaway. Our Anna Maria Island and Bradenton vacation rentals provide the perfect respite from the cold. Choose from homes with private pools, water views, and pet-friendly so the whole family can join in on the vacation.

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Thanksgiving scene on the beach

Visiting Anna Maria Island for Thanksgiving

If you are looking for a special way to spend your Thanksgiving holiday, Anna Maria Island on Florida’s Gulf Coast is the perfect destination. This charming barrier island offers a unique Thanksgiving experience filled with relaxation, serene nature and a warm holiday atmosphere.

One of the main draws of Anna Maria Island for a Thanksgiving getaway is its mild and pleasant weather. The island enjoys average temperatures in the 70s (F) during November, providing an ideal place to escape the cold. Plus this time of year tends to be much quieter than peak tourist season, making it a great time to enjoy the island’s beaches and other attractions without the spring and summer crowds.

Thanksgiving Dinner

Eat your turkey and trimmings by the beach at a number of waterfront restaurants offering holiday meals on Anna Maria Island or inDiners eating outside at an Anna Maria Island beach restaurant Bradenton.

  • Anna Maria Island Beach Café will be open on Thanksgiving Day, offering a traditional meal for pick-up (pre-order required). For those who are hungry for some beachfront dining, a breakfast will also be served in the morning.
  • Pier 22 is a waterfront restaurant in nearby Bradenton with a special Thanksgiving holiday menu starting at 11am. Reservations are strongly encouraged.
  • Bridge Street Bistro in Bradenton Beach offers a Thanksgiving buffet starting at noon, including seafood and other less traditional dishes available in addition to turkey and mashed potatoes. Reservations are required and can be made on their website.

Things to Do Over the Thanksgiving Holiday

There are lots of activities to choose from during your Thanksgiving vacation to Anna Maria Island, with options for everyone.

  • Get a head start on your holiday with the Bradenton Turkey Trot 3-Miler Fun Run. Starting at 8 a.m. on Thanksgiving morning, this event is open to all levels, and proceeds will support local food banks. Race day registration is available for cash only.
  • Explore the laid-back and quaint atmosphere of Anna Maria Island by bike. The slow traffic and flat roads make the island a great place to get around by bike for riders of any level, with trailers and kids’ bikes available for rent as well. On the northern end of the island, do your Black Friday shopping along Pine Avenue, then continue along the Anna Maria Island City Pier for a great view of the Sunshine Skyway Bridge. On the southern end, check out serene Leffis Key Preserve for wildlife viewing and bay views along the boardwalk, then stop by lively Coquina Beach across the road.
  • Rent a kayak or paddleboard and set off to explore the serene waterways of Anna Maria Island on your own. Or book a kayak tour, where you will have the opportunity to see dolphins, manatees and other wildlife. Booking a charter boat for a fishing trip or dolphin tour is a great way to experience a saltwater adventure in the Gulf of Mexico.

Where to Stay

Oceanfront pool at an Anna Maria Island condo rentalStaying in a vacation rental on Anna Maria Island over Thanksgiving has several benefits. It allows you to enjoy a more relaxed and private holiday with your family and friends, and you have the flexibility to cook your own Thanksgiving meal in a fully equipped kitchen, or order takeout from one of the island’s restaurants. Additionally, our vacation rentals offer more space and amenities than a hotel room, such as private pools and outdoor living spaces, and living rooms that the whole group can gather in.

Located minutes from Anna Maria, Coco’s Dream is a cozy canal front home with a backyard pool oasis for ultimate relaxation. The stylish Lime Kiss offers a palm-fringed pool area and a rooftop deck overlooking the Gulf of Mexico.

Anna Maria Island is a great destination for a special Thanksgiving experience. With mild weather, fewer crowds, and plenty of restaurants offering a special holiday meal, it’s a great place to enjoy the holiday with your loved ones. Book your vacation rental and start planning your Thanksgiving getaway to Anna Maria Island!

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