Anna Maria Island: Old Hollywood, Old Florida & the Perfect Winter Escape 🎬🌴

Long before Anna Maria Island became a favorite destination for winter travelers, it had already caught the attention of Hollywood.

In 1948, actress and swimming star Esther Williams and a Hollywood production crew came to Anna Maria Island to film On an Island with You, bringing the island's beaches and tropical scenery to the big screen.

Nearly 80 years later, much of what made Anna Maria Island special then is still part of its charm today.

The low-rise buildings. The relaxed pace. The free island trolley. The palm-lined streets. And, of course, the beautiful Gulf beaches.

If you're looking for an Anna Maria Island vacation rental where you can experience that classic Florida atmosphere for yourself, Dans Florida Condos has homes at Runaway Bay that offers a comfortable place to settle in for a few days, a few weeks, or an entire winter.

When Hollywood Came to Anna Maria Island

In 1948, Hollywood came to Florida.

On an Island with You, starring Esther Williams, was filmed in part on Anna Maria Island, showcasing the area's tropical scenery and beaches during a time when the island was still a relatively quiet Florida community.

Williams was one of Hollywood's biggest stars of the era, famous for her elaborate swimming performances and musical films.

The movie offered audiences a glimpse of a tropical paradise — and Anna Maria Island had the scenery to make the impression last.

Today, you can still walk the same island and understand why it made such a memorable backdrop.

Nearly 80 Years Later, Old Florida Is Still Here

One of the things that makes Anna Maria Island different from many other Florida beach destinations is what you don't see.

You won't find a skyline filled with towering beachfront hotels.

Instead, much of the island retains its low-rise character and relaxed coastal atmosphere.

The island is easy to explore, whether you're walking along the beach, riding the free trolley, browsing local shops, or simply finding a quiet spot to watch the Gulf.

It's a slower style of Florida vacation — and that's exactly what many visitors come here to find.

Things to Do on Anna Maria Island

You don't need a packed itinerary to enjoy Anna Maria Island.

Some of the best experiences are wonderfully simple:

• Walk the Gulf beaches at sunrise.

• Spend a lazy afternoon by the water.

• Explore the island using the free trolley.

• Visit the island's shops and local restaurants.

• Watch the sunset over the Gulf.

• Go fishing from the community pier.

• Enjoy time on the water.

• Play tennis or pickleball.

• Relax by the pool after a day at the beach.

For visitors staying longer, the island also makes a great home base for exploring the surrounding Bradenton and Sarasota areas.

Why Anna Maria Island Is Perfect for a Winter Getaway

When temperatures drop across much of the country, Anna Maria Island remains a popular destination for travelers looking for sunshine, warm weather, and a slower pace.

That's why Anna Maria Island winter rentals are especially popular with guests looking to escape the cold for an extended stay.

Instead of packing your winter vacation into a long weekend, imagine having weeks to enjoy island life.

Morning coffee.

A walk on the beach.

Lunch in the sunshine.

An afternoon by the pool.

And a Gulf sunset to finish the day.

That's the beauty of spending winter on Anna Maria Island.

Stay at Runaway Bay, Just Across From the Beach

For guests looking for an Anna Maria Island beach rental, Dan's Florida Condos offers vacation condos at Runaway Bay.

The community sits across the street from the beach, making it easy to enjoy the Gulf whenever you want.

And when you're ready to come back from the beach, Runaway Bay offers plenty to enjoy right on the property.

Guests can enjoy:

• Anna Maria Island's largest heated saltwater pool

• Private beach access

• A fishing pier

• Tennis and pickleball

• Fitness facilities

• Community Wi-Fi

• Charcoal Weber grills

• Comfortable vacation condos for short and extended stays

It's a combination that makes Runaway Bay a convenient home base for exploring Anna Maria Island — while still giving you plenty of reasons to stay close to home.

Experience the Anna Maria Island That Hollywood Discovered

In 1948, Hollywood came to Anna Maria Island because its beaches and tropical setting looked like something out of a movie.

Nearly eight decades later, the island still has that unmistakable old-Florida feeling.

The scenery has changed in some ways, of course. But the things that make Anna Maria Island special remain remarkably familiar: beautiful beaches, palm trees, low-rise communities, warm Gulf waters, and a relaxed pace of life.

Maybe that's why the island continues to feel a little bit like a movie set.

Except this time, you're the one staying here. 🎬🌴

Ready for Your Anna Maria Island Winter?

If you're dreaming about a Florida winter filled with sunshine, beach walks, pool days, and the laid-back charm of Anna Maria Island, explore some our vacation rentals at Dan's Florida Condos.

Stay across the street from the beach, enjoy resort-like community amenities, and make Anna Maria Island your home away from home.

Explore Runaway Bay condos and start planning your Anna Maria Island getaway today.