Discover 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.

We look forward to making your stay at our home on Anna Maria Island a pleasant one that you will repeat for many years.

Find a Vacation Home

How to Love Anna Maria Island Like a Local

Here on Anna Maria Island, there are endless ways to enjoy your stay. Take your pick of beautiful island beaches, quaint coastal villages, and some of the freshest Florida seafood around! Endless sunny days on ...
Read More

3 New Must-Try Restaurants on Anna Maria Island

Are you planning a trip to Anna Maria Island? Maybe you’re a local looking to try something new. Check out these 3 must-try dining experiences! Each of these restaurants located on the island are great ...
Read More

Benefits of Booking a Stay with Serendipity

Vacation is your time to kick back and relax! That’s why Serendipity offers services like flexible check-in and grocery delivery, so you don’t have to sweat the small stuff. Less Traffic, More Vacation Especially during ...
Read More

Introducing Serendipity Circle Home Care and Advertising Services

At Serendipity, we take pride in the time and effort dedicated to our properties to create a memorable experience for our guests. Our desire is to continue to create new experiences on Anna Maria Island ...
Read More

Be the First to Know

Sign up for our Newsletter and be the first to know about our updates and promotions.

We’ll make sure your next vacation is relaxing and fun!

  • This field is for validation purposes and should be left unchanged.