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.

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.

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…

Beautiful Sea La Vie Property Now For Sale

It’s bittersweet to announce the listing of our Sea La Vie property for sale. It has been a favorite rental…

Long Term Rentals Available [Plus the Latest COVID Update]

Although life isn’t back to “normal” yet here at Serendipity Anna Maria, there is one thing we are celebrating: We…

Start Your Vacation

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