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


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.”


Putting our Customers first.


By maintaining a friendly and helpful Attitude


And treating all of our clients with Respect


While Enjoying life in the process!

Latest Articles & Updates

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

Serendipity Anna Marias Response to COVID-19

Dear Current & Future Guests, Thank you for your patience as we work with you to accommodate your individual needs to…

Waffels on Anna Maria Island

11 of the Best Foodie Spots in Anna Maria Island

Is there a better way to experience a city than to eat your way through it? We think not. And…

Planning your Perfect Romantic Getaway in Anna Maria Island

Looking to wow your significant other with the perfect romantic getaway? There’s no better place to whisk them away to…

Start Your Vacation

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