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History of Siesta Key

Modern-day Siesta Key is famous for its gorgeous beaches, lovely emerald waters, and numerous restaurants. Consequently, this Florida gem attracts hundreds of thousands of vacationers yearly, making it one of the state’s tourist hotspots. But behind the picturesque views and thrills lies an intriguing narrative of Siesta Key history dating back to the early 20th century.

A Tale of Humble Beginnings

At the turn of the 20th century, Siesta Key went by Little Sarasota Island or Sarasota Key. The few families that lived there primarily practiced fishing, while the island featured thick vegetation and a list of wild animals, including several venomous snakes. Things took a turn when in 1906, Captain Louis Roberts and his dear wife, Ocean Hansen Roberts, converted their boardinghouse into a hotel. Mrs. Roberts’ culinary skills, particularly her clam chowder recipe, gained her a reputation and began to draw A-listers, including Hollywood stars. A year after the hotel opened its doors, Captain Roberts and two partners, Harry Higel and E. M. Arbogast, teamed up to form the Siesta Land Company, with the trio later renaming the island Siesta Key. Harry Higel later used his prowess to market the island while improving its surroundings to draw more guests. In 1917, Harry Higel, the then-mayor of Siesta Key, supported the establishment of the island’s first bridge, opening up the area to more guests. Nearly 10 years later, in 1926, the county built the island’s second bridge and platted the division of the northern part of the Key. Development slowed following the Great Depression but took off again in the 40s and 50s, with several famous artists making the island their residence.


Siesta Key has grown in leaps and bounds over the decades, with the island now hosting hundreds of excellent hotels and numerous world-class restaurants. The warm winter weather, sugar-white sandy beaches, and beautiful turquoise waters persist, drawing massive droves of vacationers. Many of the island’s historic pictures hang at the Sarasota County History Center and the Crescent Beach Grocery at the junction of Stickney Point Road and Midnight Pass.

Reserve Your Siesta Key Rental

Few Florida destinations match the charm and thrill of Siesta Key. This beautiful barrier island offers vacationers an experience of a lifetime thanks to its impressive collection of attractions. At Rent Siesta Key, we offer an expansive selection of cozy vacation rentals, including beach-view condos, pool homes, and on-the-beach houses for the ultimate getaway experience. Contact us today to book your Siesta Key rental and enjoy a laid-back island vacation.