Anna Maria Island Vacation Homes

Serendipity Calls: Experience Paradise in Our Luxurious Anna Maria Island Homes.

Our Most Popular Vacation Homes

Pack your bags, park your car, and get ready for the vacation of a lifetime - Serendipity will take it from there!

Cloud 9

Cloud 9

Anna Maria Island, FL

fanta-sea-47

Fanta-Sea

Anna Maria Island, FL

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Serendipity Deux

Anna Maria Island, FL

From Our Happy Guests

Kind words from those who have stayed with us.

Amanda Parah
3 months ago
This home and location exceeded my expectations! It was the cleanest home I’ve stayed in, the pool/spa/outdoor space was fabulous! Well done! ...
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SANDRA RIFFE
3 weeks ago
This home and the hosts were amazing. The home had everything you could ever need and then some. Our favorite was how we did...
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Laura Carasso
5 months ago
We had a wonderful stay in this beautiful home. Pool and spa area was a great place to chill after a day on the...
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Tim Pereira (Cooney)
3 months ago
We thoroughly enjoyed our stay at Serendipity and would do it again. The house is lovely and comfortable for a family of 5 adults and...
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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.

Update on Hurricane Helene Recovery

October 1, 2024

Dear Valued Guests and Friends, We hope this message finds you safe and well. In the aftermath of Hurricane Helene,…

The Best Bakeries on AMI

September 18, 2024

Imagine it with me: you wake up early to take in the beautiful ocean views from the comfort of your…

Fall Events on AMI: 2024 Edition

September 6, 2024

Get ready to fall into a great time and plan your autumn adventure on Anna Maria Island. Serendipity has put…

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

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