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

52574-138870-xzZy--HPrjKjrJew50IgKKUsL8pI6h5oSWHRuXtfv3sM-63adacfd1268e

Serendipity Deux

Anna Maria Island, FL

From Our Happy Guests

Kind words from those who have stayed with us.

Kiersten Chavis
12 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...
Read More »
Mary Ann Henderson
10 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 &...
Read More »
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! ...
Read More »
Bill Whearty
8 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...
Read More »

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.

Stocking Your Fridge: The Best Grocery Stores on AMI

No one wants to have to worry about groceries while on vacation. With this guide, you can cast those worries…

January 26, 2026

Don’t Miss a Game: Football Season on AMI

Playoff season is finally here! Even if your team didn’t make the cut, this season is one not to be…

January 12, 2026

Anna Maria Island: A Snowbird’s Paradise

Is there something about the winter months that has you wanting to travel? You may be a snowbird at heart….

January 1, 2026

FAQ

More FAQ

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.