Discover Anna Maria Island

Serendipity Anna Maria is committed to the quaint island feel. With charming local shops and beautiful beaches Anna Maria Island has received several travel awards and is the perfect place to get away for your vacation.

We look forward to making your stay at our home on Anna Maria Island a pleasant one that you will repeat for many years.

Find a Vacation Home

Island Plaza is one of Anna Maria Island’s Hot Spots

There are some fun and interesting shops and eateries in the area, but some of our favorites are in the Island Plaza located right on historic Bridge Street. Back in April, the travel bloggers at ...
Read More

See Our Newest Luxury Vacation Home

Change is in the air at Serendipity. We’re excited about it and think you will be excited too. For years, we have offered luxury vacation home rentals on Anna Maria Island and people love coming ...
Read More

See Anna Maria Island on the Island Trolley

Anna Maria Island is beautiful and both residents and visitors love to walk our beaches and explore the island. While many things are within walking distance, not everything is. In those instances, the Island Trolley ...
Read More

4th of July on Anna Maria Island

The 4th of July is the biggest holiday celebration in the summer. It’s the unofficial peak of the season and many communities across the United States have events to observe the birthday of the nation. ...
Read More

Be the First to Know

Sign up for our Newsletter and be the first to know about our updates and promotions.

We’ll make sure your next vacation is relaxing and fun!

  • This field is for validation purposes and should be left unchanged.