Beginning around 1890, the William Deerings began wintering in Florida, first around St. Augustine, and later in the vicinity of Miami. Visiting them, both Charles and his half-brother became deeply interested in South Florida. Around 1908, Charles purchased some 212 acres of land in Buena Vista. In 1910, he hired Clinton Mackenzie to design a Spanish-style villa for the property. He hired the great Chicago landscape architect Ossian Cole Simonds to lay out the grounds. Here he supported the New York Botanical Garden by providing them 25 acres to grow cacti. Around this time, Deering made the acquaintance of botanist David Fairchild and allowed the US Department of Agriculture to establish an experimental station on 25 acres of his property. Deering became an avid naturalist and preservationist. The book "Ornamental Gardening in Florida" by Charles Simpson is dedicated to him.