Naples was founded in 1887 by Walter N. Haldeman, the owner of the Louisville Courier Journal in Kentucky. The next year, he constructed the Palm Cottage, the Naples Hotel, and a 600 foot pier at 12th Avenue South.

By the early 1920's, Naples was still a small fishing village when Barron G. Collier bought 900,000 acres of land in what is now Collier County. Born in Memphis, Tennessee, Collier made his fortune selling billboard advertising on streetcars and railways. He was the driving force behind the building of the Tamiami Trail across the Everglades, financing and overseeing the project to its completion in1928.

Everglades City was his development center and county seat, where he built port facilities, a machine shop, and a sawmill. He owned almost every house in town and most of the residents were his employees.

Marco Island was settled in 1870 when W. T. Collier of Tennessee (no relation to Barron Collier) arrived in his schooner. The Olde Marco Inn on Palm Street is a restaurant occupying part of W. D. Collier's Inn, built in 1883.

The site of a famous archaeological expedition in 1895, Marco remained an isolated farming and fishing community until the 1920's when the Olde Marco Ferry and the first railroad link from the mainland were completed. During the late 1940's, Marco Island was developed by the Mackle Brothers and others, adding most of the present day roads and canals.