Many cities throughout the Sunshine State have become increasingly industrialized over the years, making way for high-rises and busy streets. However, there is one special place that you can still experience that Old Florida feeling: Anna Maria Island. This seven-mile stretch of shore just off the coastline is the perfect place to relax and unwind in one of our comfortable Anna Maria Island vacation rentals. AMI remains proud of its history and strives to keep the slow-paced lifestyle that Florida originated with.

About the History
Anna Maria Island was first discovered by the Native American Timucua and Caloocan tribes. The Spanish explorer Hernando de Soto passed the island in 1539, and it was eventually settled by Madison Post. Post, who served as the mayor of Tampa, named the island for his sister-in-law Anna and his wife Maria.
George Emerson Bean was Anna Maria Island’s first permanent resident, setting up his homestead in 1892. This area is now known as Bean Point. Some of the first buildings to appear during the early days of Anna Maria Island are still available to visit today.
The island has been very intentional in maintaining their traditional setup, choosing to focus more on encouraging local business instead of welcoming too many national chain businesses. In fact, the island has imposed height restrictions on buildings and has forbidden high rise apartments and offices. The tallest building on Anna Maria Island is a three-story condo that has apparently been grandfathered in.
“Old Florida” Buildings and Structures
The term “Old Florida” is defined as anything from the mid-20th century or before. Many of the buildings and structures found throughout Anna Maria Island today still maintain that Old Florida charm. For instance, Historic Green Village is a self-preserved community of restaurants, shops, and houses that features restored buildings that date back as far as 100 years ago.
Another popular Old Florida attraction in Anna Maria Island is the Old Jail, which was originally built in 1927 and has been preserved incredibly well over the last 90 years. Visitors from near and far love coming to the Old Jail to get a photo op and learn more about the history of the island.
While you’re in town, you’re bound to make a stop at the City Pier, which was originally built in 1911. Granted, the pier has had to be restored and rebuilt several times due to storm damage over the decades, but it has still managed to maintain that Old Florida charm that Anna Maria Island is known for.

A Casual Experience
The Old Florida charm of Anna Maria Island can be found around every corner. You won’t find busy thoroughfares or crowded buildings anywhere on the island; instead, the locals put an emphasis on a slower-paced way of life that visitors from all around can appreciate.
As we mentioned, the vast majority of businesses and restaurants on the island are locally operated. You’d be hard-pressed to find a chain establishment anywhere on AMI! It’s not uncommon to spend hours chatting with the locals and getting to know the native business owners that have called Anna Maria Island home for decades.
Plan Your Next Vacation
Your trip to Anna Maria Island is sure to provide the rest and relaxation you deserve. After you spend the day exploring AMI, you can take that relaxation even further by staying in one of our Anna Maria Island rentals with a pool! Ready to play on your Florida getaway? Contact us today to learn more about our Anna Maria Island vacation rentals.
The Art Community
Anna Maria Island’s art community has played a big role in maintaining the Old Florida feeling. All throughout the year, local artists hold workshops, outdoor festivals, art shows, and galleries, and paintings by local artists are often featured inside small shops. Supporting Anna Maria Island local artists is just one way that you can show your enthusiasm for the Old Florida atmosphere.


