The holidays don’t have to mean snow and cold on Anna Maria Island. They can be all about sunshine, family, and easygoing island traditions. With Anna Maria Island Accommodations, you’ll find the perfect vacation rental to gather together, whether it’s a cozy cottage steps from the beach or a larger home for the whole family. And right now, our Sunshine and Savings promotion makes celebrating the season even sweeter.

Book by October 2, 2025 for travel through December 26, 2025, and choose your savings:

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Halloween on Anna Maria Island is all about family fun, community spirit, and a touch of island charm. Fall is considered the island’s “slow season, ” which means fewer crowds, cooler breezes, and an even more relaxed pace. Making it one of the best times to visit our special island. Whether you’re traveling with little ones ready to trick-or-treat or searching for adult-friendly festivities, you’ll find safe and exciting ways to celebrate across Anna Maria, Holmes Beach, and Bradenton Beach. Even just a short drive away, Bradenton and Lakewood Ranch host lively fall festivals and spooky celebrations of their own, that gives you endless ways...

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Anna Maria Island is known for its sugar-white sands, turquoise Gulf waters, and easygoing coastal charm. Yet tucked just three minutes from Holmes Beach lies a vacation estate that redefines island indulgence. The Palace, a brand-new seven-bedroom, seven-and-a-half-bath masterpiece, lives up to its name with a perfect fusion of sophistication, entertainment, and resort-style amenities designed for only the most discerning of guests.

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Every stretch of sand on Anna Maria Island has its own unique charm. Whetheryou’re visiting for relaxation, adventure, or family fun,there’s a beach that fits your vacation style perfectly.

For Sunset Lovers: Bean Point

The quiet shores of Bean Point are ideal for romantic evenings and picture-perfect sunsets. This beach is a no-swim zone, but is not short on beautiful views and amazing sunsets.

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Fall on Anna Maria Island is the perfect mix of sunshine, warm Gulf breezes, and peaceful beaches. It’s also the season to take advantage of our special offer! Book select homes online for 10% off or call us for up to 15% off 7+ night stays. Guests who qualify with a call-in booking will also receive a Mastercard gift card to spend during their stay.

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Planning your next getaway to Bradenton Beach? Whether you’re booking a romantic escape, a family vacation, or a solo seaside reset, now’s the perfect time to plan your trip. We’re thrilled to introduce three new ongoing promotions that make it easier than ever to save on your stay, and spend more time soaking up our island sunshine!

From value homes perfect for budget-conscious travelers to smaller vacation rentals walkable to the beach. These deals give you more reasons to escape to Anna Maria Island southern gem!

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Dreaming of your next beach getaway? Let Anna Maria Island sweep you off your feet. From sugar-white sands and turquoise Gulf waters to the cozy charm of Holmes Beach and Bradenton Beach, this Florida gem has it all. Whether it’s your first time or a return trip, discover local-approved spots to dine, unwind, and soak up the laid-back coastal lifestyle.

Whether you’re planning your first vacation or returning for another relaxing stay, here’s your local-approved guide to dining and entertainment on Anna Maria Island, Florida, including...

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Planning a trip to Anna Maria Island during the summer months? You may have noticed that it’s also Florida’s rainy season. You don’t have to cancel your trip, this is Florida! A typical summer day here might bring sunshine in the morning, a quick splash of rain in the afternoon, and a jaw-dropping sunset in the evening.

Rainy days on your vacation aren’t the end of the fun, they’re just an excuse to explore the area from a new angle! Cozy up at your vacation rental or discover local hidden gems...

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Looking for the perfect Florida beach destination for the Fourth of July? Celebrate Independence Day 2025 on Anna Maria Island, where coastal charm meets classic Americana. From pirate-themed parades and waterfront fireworks to family-friendly dining and Gulf views, Anna Maria Island offers something special for everyone this holiday weekend.

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PRIME VACATIONS is proud to be featured on Bay News 9, highlighting the remarkable resurgence of vacation rentals as tourism flows in, rejuvenating our community after the challenges posed by last year’s hurricanes, Helene and Milton.

Eric Pullen, our Vice President of Growth and Development, highlighted the extensive repair work across all 600 properties we manage on Anna Maria Island. With about 70% of our inventory back online by Christmas 2024 and 90% expected by early May...

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