Make a Reservation

Check-in:

Check-out:

Guests:

Children:

 

 

Searching...

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.

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...

Woman wearing hat looking out at the water - Serendipity Anna Maria

5 Things To Do During Winter Family Vacations To Anna Maria Island

Do cold, dark winters get you down in the dumps? You’re not alone. About 10 to 20 percent of people...

Heart in the sand at beach- Serendipity Anna Maria

The Magical History Of Anna Maria Island

The history of Anna Maria Island has many periods of discovery. As the first explorer, Ponce de Leon came to...

Start Your Vacation

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