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.

Mary Ann Henderson
6 months ago
We recently stayed at the Serendipity Gulf property. We had 7 adults & a baby. Everything was perfect. Very clean. Such a beautiful property &...
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Kiersten Chavis
7 months ago
The house was nothing short of amazing. This was our first time to AMI and have absolutely fallen in love with the area. Rick was...
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Bill Whearty
3 months ago
We had a large group of friends celebrate my wife's 50th. Between 18 people we had a few rental properties. Cloud 9 was ground zero...
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Amanda Parah
a year 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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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.

A Guide to Travel Insurance Basics

When you think of the word insurance, what comes to mind?  You might think of medical, car, or even home…

December 1, 2025

Exciting News for Prospective Partners + Serendipity Homeowner FAQ

Serendipity has exciting news: Our team is growing! Join us in welcoming Sabrina as our full-time property manager. Sabrina is…

November 28, 2025

Serendipity Announces New Partnership with PGA Coach Justin Smith

Serendipity has partnered with PGA-Certified coach Justin Smith to offer our guests the amazing opportunity for a 1-on-1 session during…

September 24, 2025

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