A Brief History of Siesta Key

Long before Siesta Key came to be known for what it is today, packed with man made attractions and remarkable Siesta Key vacation rentals, it was a quiet island infested with mosquitoes, snakes, shrubs, wild cats and aggressive boars.

All of this did little to encourage new settlers to this island up until the 20th century. By the mid-1940s it only had a population of about 300 people.

However, in 1906, things began to change for the better when the wife to Captain Roberts decided that her culinary prowess in the kitchen was something of a raw talent that would do more good in the outside world.

They converted their large boarding home into a hotel and hosted northern visitors during the long winters. Mrs. Roberts’ cooking was so good that her famous seafood recipes were whispered far and beyond and attracted Hollywood elites and members of the Eastern Establishment to her doorstep.

The Siesta Land Company

Barely a year after opening the hotel, Cpt. Robert teamed up with other two partners to form the Siesta Land Company, which mapped out the island and renamed it to Siesta Key. With its new name, modern Siesta Key history then began in full force. It was renamed to a far more appealing and fresher name than her predecessors, Clam Island, Little Sarasota Island, or Sarasota Key.

Harry Higel’s Development of Siesta Key

The most iconic and notable member of the founding group was Harry Higel, then-mayor of Sarasota. He was a visionary and a developer who worked relentlessly over the years trying to shape Siesta Key into a land of modern tourist attractions. He began by launching lots of advertising and dredging three canals through the Siesta Village area and connecting them to the bay.

Ever the go-getter, Higel went ahead and opened the Higelhurst Hotel in 1914 on the shore at Big Pass, a bit north on the Key. A lot of credit goes to Higel for his commitment to building a bridge to Siesta Key, which was completed in 1917.

In the meantime, its sister bridge went under construction and connected the southern end of the island to the mainland at Stickney Point. This bridge was first opened in 1927, however development started to slow down during and after the Great Depression.

Development started to pick up again in the 40s and 50s after several well-known artists moved to the island and architects Paul Rudolph and Ralph Twitchell build a number of homes on the island.

The Attractions and Draws of Siesta Key

Today Siesta Key boasts a permanent population of 6,500 inhabitants and draws tourists to its incredible attractions and beaches from all corners of the world, averaging around 350,000 every year with growing numbers in recent years.

What brings so many visitors to Siesta Key? The ever-white sandy beaches that stay cool to the touch, warm winters, thrilling outdoor activities, and fantastic ocean views are just a few of the gems that the island has to offer.

What to Do When You Visit Siesta Key

If you’re intrigued now and want to visit, a few suggestions can go a long way in making your Siesta Key experience more satisfying and full of fond memories that will keep you coming back for more.

Your first attraction stop would probably be Siesta Beach, as it’s known for its fabulous white sands, beautiful umbrellas, and magnificent blue skyline. Lifeguards are on duty from Memorial Day to Labor Day, however the water is very safe for swimming during the fall and winter months, and quite shallow close to shore.

Crescent Beach is another excellent beach option on the island that is typically less crowded since it is undeveloped. White powdery sands and beautiful sunsets are some of the unique attractions of this beach, as well as world-class snorkeling/scuba diving at the Point of Rocks.

Boat tours can be very fun for groups and are hugely popular among locals and visitors alike. On a hot sunny afternoon, there’s nothing like a cool breeze brushing against your face as you cruise through the ocean and view the local scenery and marine life including dolphins.

Visitors can also explore a handful of nearby local museums and historic sites to learn about Sarasota and Siesta Key history. Or spend countless hours exploring the dozens of local stores, spas and restaurants in Siesta Village.

Of course, this is just a brief list, as this island is packed with sensational Siesta Key vacation rentals, attractions, beach escapes, and intriguing history that you won’t want to miss the next time you’re planning on being in Southwest Florida.