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
7 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
8 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
5 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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Jade Bassett
in the last week
Had an incredible stay at their property Waves this past week!! The house was equip with everything we needed. The best part was we came...
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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.

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

The Festive AMI Traveler’s Guide to Celebrating Christmas and New Year’s

There is no better place to spend the holiday season than Anna Maria Island. Sure to be your home away…

December 19, 2025

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