Recently in Vacation Ideas.

Key Lime Cottage: Your Dreamy Gulf Front Hideaway

Welcome to Serendipity's newest property, Key Lime Cottage. This cozy cottage is just steps away from the North Shore Coast on Anna Maria Island. Settle in and let the beachy vibes and Old Florida charm ...
Read More

Get Ready to Play: Pickleball on AMI

Caught up in the growing craze that is pickleball? Well, grab your paddles and get ready to play because there is plenty of pickleball action to be had on Anna Maria Island. Whether you’re a ...
Read More

The Center of AMI: A Community Staple

The Center of Anna Maria Island  407 Magnolia Ave, Anna Maria, FL 34216 Hours of Operation  Monday 7 am-8 pm Tuesday 7 am-8 pm Wednesday 7 am-8 pm Thursday 7 am-8 pm Friday 7 am-7 ...
Read More

Capturing the Sound of AMI: The Best Places for Live Music

If you're looking to enjoy some live music during your stay on Anna Maria Island (AMI), you're in luck! The island offers plenty of fantastic venues where you can catch a show. Serendipity has compiled ...
Read More

The Arts & Culture Scene on Anna Maria Island

Nestled along the picturesque shores of Anna Maria Island, a vibrant arts scene thrives, captivating both locals and visitors alike. From enchanting theatrical performances to diverse art galleries and engaging workshops, the island is a ...
Read More
FAQ Beach Image

Serendipity: Frequently Asked Questions

Questions are bound to come up when planning for any vacation. With so many moving parts, it is understandable that you want to ensure things go as smoothly as possible. Serendipity has you covered. Our recently ...
Read More

Events on AMI: Spring 2025

Looking for the perfect time to visit Anna Maria Island? Or maybe you already have one of Serendipity's beautiful properties lined up for a spring-time vacation! One thing is for sure; spring is in bloom and the island is bursting with things to do! March Events on ...
Read More

A Peek Inside Our Beautiful Anna Maria Island Vacation Rentals

Serendipity offers a selection of 11 rental properties, ensuring that you will find the perfect accommodation for your stay on Anna Maria Island. With a variety of options available, each property provides a unique experience ...
Read More

Events on AMI: Winter 2025 

Anna Maria Island is the perfect winter getaway. It is absolutely brimming with picturesque beaches, warm weather, and, best of all, plenty to do. The island is bustling with farmers’ markets, fishing adventures, and so much more! Follow along ...
Read More

A Day Out at Anna Maria Island’s Farmers Markets

There is no better way to spend a morning than at a farmer's market, and Anna Maria Island's Farmers markets are some of the best in the state. With vibrant, fresh produce and unique local arts and ...
Read More

Getaway with Anna Maria Beach Cottages: Cottage 110A

Looking for a cozy place to stay while visiting Anna Maria Island this winter? Our friends at Anna Maria Beach Cottages have just the place for you! Cottage 110A is situated near the beach, between ...
Read More

The Butcher Shops and Fresh Fish Markets of AMI

Nothing beats a home-cooked meal, and quality ingredients make all the difference. A prime cut of meat or a fresh local catch can really shine as the centerpiece of any meal and make all the ...
Read More

Monthly Events on AMI: Winter 2024

Serendipity is set to reopen in early November, inviting you to experience the island paradise of Anna Maria Island this winter. As you prepare for your stay with us, we’ve compiled a list of events ...
Read More

The Best Bakeries on AMI

Imagine it with me: you wake up early to take in the beautiful ocean views from the comfort of your luxurious vacation rental, do your morning stretches, or join in for a sunrise yoga session. ...
Read More

Fall Events on AMI: 2024 Edition

Get ready to fall into a great time and plan your autumn adventure on Anna Maria Island. Serendipity has put together some of our favorite fall events on AMI during your stay with us on ...
Read More
Pier fishing on Anna Maria Island

Fishing Adventures: An Angler’s Guide to AMI

Anna Maria Island, a coastal paradise, offers a diverse range of fishing experiences for enthusiasts of all ages and skill levels. Whether you're seeking a leisurely day with a local brew and a line in the ...
Read More

AMI by Air, Land, & Sea: Guided & Self-Guided Island Tours

There are so many ways to explore the wonder of Anna Maria Island. What better way to do so than by treating yourself to a tour? Whether by air, land, or sea, you can choose ...
Read More

Monthly AMI Events | ’24 Summer Edition 

Getting ready for your summer getaway to Anna Maria Island? The hottest season has some of the coolest events on the island! We have put together a list of some of our favorite monthly AMI ...
Read More
theme park couple

Get Ready for Adventure! Theme Parks Near Anna Maria Island

Anna Maria Island is home to wonderful museums & markets, delicious dining, and so much more. But if you are looking to add a little bit of magic during your stay on Anna Maria Island, ...
Read More
Beach Park Walkway

Discover Outdoor Splendors with a Local Guide to Anna Maria Island’s Parks

Anna Maria Island is a veritable paradise with sugar sand beaches and sunny summer days. It is unsurprising that AMI is a hub for vacationers and business travelers. And while there is joy to be ...
Read More
Coffee on beach

Coffee Shops on AMI + Transport & Day Trip Tips

Favorite Coffee Shops on AMI Looking for a taste of paradise to take your vacation to the next level? Or maybe your “work-cation” needs a caffeine boost to keep that workflow flowing? Perhaps you just ...
Read More

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