Summer Vacation Sale!

Save big by booking a 7 night vacation at either Retro Retreat or Surf Shack during August or September! Space is limited, reserve your vacation home today!

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.

The Perfect 4-Day Summer Getaway Trip to Anna Maria Island

The cool aquamarine waters of the Gulf of Mexico splash onto the white sandy beaches. Happy vacationers float and play…

Girl walking on the beach

Landmarks, Parks, and Nature: How to Have the Perfect Family Getaway in Anna Maria Island

It’s hard to plan a family reunion. Families are spread all across the country, living different lives in different time zones….

Birds flying over beach water - Serendipity Anna Maria

Why Anna Maria Island is Perfect for a Vacation

Whether you’re looking for a honeymoon destination, a retirement dream vacation, or a getaway with family and friends, Florida is…

Start Your Vacation

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