Before it was an inviting tourist destination full of beautiful Siesta Key rental properties, the island was a wild, over-run island booming with wildlife. Let’s take a look at how Key got to where it is today.
Humble Beginnings
The first inhabitants of Siesta Key were Native Americans, who lived on the island for thousands of years before the arrival of Europeans. The Calusa Indians were one of the most prominent tribes in the area, and they built impressive shell mounds that still exist today. These mounds were used for a variety of purposes, including as ceremonial sites and as places to live.
In the 16th century, Spanish explorers arrived in the area and established a settlement in nearby Tampa Bay. However, they did not establish a permanent presence on Siesta Key, and the island remained largely untouched by Europeans until the 19th century.
Heating Up
In the late 1800s, Siesta Key became a popular spot for wealthy Northerners who were looking for a warm and sunny retreat during the winter months. These visitors built large, luxurious homes on the island, some of which still exist today.
During this time, Siesta Key was also home to a thriving fishing industry. The island's abundant waters provided an abundance of fish, and fishermen would sell their catch to markets on the mainland.
In the early 20th century, Siesta Key's population began to grow, and the island became more accessible with the construction of a bridge that connected it to the mainland. During World War II, Siesta Key was used as a training ground for soldiers, and a military radar station was built on the island.
After the war, Siesta Key experienced a boom in development, and the island's population continued to grow. The tourism industry also began to take off, and Siesta Key became a popular destination for visitors from around the world.
In the 1960s and 1970s, Siesta Key became known for its vibrant counterculture scene. Hippies and artists flocked to the island, and it became a hub for creative expression and free-spirited living.
Something for Everyone
Today, Siesta Key remains a popular destination for tourists, and its stunning beaches and lively nightlife continue to attract visitors from around the world. But the island's rich history can still be seen in its architecture, its landmarks, and its natural beauty.
One of the most iconic landmarks on Siesta Key is the Siesta Key Beach Pavilion, which was built in the 1950s and remains a popular spot for visitors today. The pavilion's unique design, with its curved roof and colorful tiles, is a nod to the island's history and its artistic heritage.
Another landmark that pays homage to Siesta Key's past is the Siesta Key Drum Circle, which takes place every Sunday evening on the beach. The drum circle is a gathering of musicians and dancers who come together to celebrate the island's creative and free-spirited culture.
Floridians’ Favorite Getaway

In addition to its landmarks, Siesta Key's natural beauty is also a testament to its rich history. The island's beaches are renowned for their white sand, which is composed of pure quartz crystals that were formed millions of years ago. This sand is so fine that it feels like powder underfoot, and it is one of the main attractions that draws visitors to the island.
Siesta Key's history is a complex and fascinating one, and it is evident in every corner of the island. From its Native American heritage to its role as a hub for counterculture in the 1960s and 1970s, Siesta Key's past is as vibrant and diverse as its present-day reputation as a tourist destination.
Where to stay in Siesta Beach
There’s no shortage of Siesta Key vacation rentals, but which part of the island is right for you?
If you're looking for luxury, there are several high-end hotels and resorts that offer stunning views of the Gulf of Mexico. For those who prefer a more laid-back vibe, there are cozy beachfront cottages and bungalows that offer a more intimate experience. And if you're traveling on a budget, there are also plenty of affordable options, including motels and vacation rentals.
As a trusted Siesta Key Property Management provider, we have a slew of rental options for guests to choose from. Check out our listings and give us a call today!