Paradise on 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.

Popular Rentals

Park your car, Bring your bathing suit and we will supply the rest – You are an islander now.

From Our Happy Guests

Kind words from those who have stayed with us.

Brandy Scott
a week ago
There are no perfect words to describe how AMAZING Serendipity is! Our family of 7 (4 adults, 3 children) feel so lucky that our Coronavirus...
Natasha Rivera
a year ago
Loved it will go back white sand warm water
Matthew Hazard
a year ago
An ultimate type of relaxation; very nice.
Jackie Griffin
a year ago
I love this place. I want to go back. I had the privilege of visiting friends and I was shocked. It's more...

Featured Areas

We offer exquisite vacation rentals across Anna Maria Island.

Serendipity Anna Maria Island

Anna Maria

Beautiful, Tranquil & Plenty of Sunshine

Serendipity Anna Maria - Father and daughter walking on beach

Waterfront

Your Vacation is Only Steps From the Water

Boy paddle boarding - Serendipity Anna Maria

Coastal View

Enjoy the beauty of Anna Maria Island

Our Core Values

Our dedicated team aligns with our simple core values “C.A.R.E.”

C

Putting our Customers first.

A

By maintaining a friendly and helpful Attitude

R

And treating all of our clients with Respect

E

While Enjoying life in the process!

Latest Articles & Updates

Read more about Anna Maria Island and what it has to offer your next vacation.

Everything You Need, Right Where You Are [Grocery Delivery Info]

Vacationing is all about relaxing right? It’s about ease and comfort. It’s about escaping the daily hassle of life.  So…

Travel with Confidence [Update to COVID-19 Policies]

This year has been unusual, to say the least. The COVID-19 pandemic has affected everyone, including their travel plans for…

Restrictions Have Been Lifted for Short Term Vacation Rentals

Serendipity Anna Maria is happy to report that effective May 21st, 2020, restrictions on vacation rentals have been lifted. This…

Start Your Vacation

You’ve Earned it! We’ll make sure your vacation is relaxing and fun.