From 1835 to 1842 the vastly outnumbered Seminole Indians fought the U.S. Army to a stalemate in the longest and bloodiest Indian war in U.S. history. A chain of forts around the outskirts of Collier County were reactivated when a third and final fight with the Seminole broke out in 1855. The few surviving Seminole retreated deep into the Everglades and Big Cypress Swamp where they developed a culture suited to the climate and terrain of south Florida.

A river and two inlets are named for the first settlers in the Naples area, Roger Gordon and Joe Wiggins, who moved here in the 1860's. For the next few decades, magazine and newspaper stories telling of the area's mild climate and abundant fish and game likened it to the sunny Italian peninsula. Naples quickly gained a reputation as a winter resort. Social life revolved around the Naples Hotel, which has played host to many celebrities. Barron Collier's completion of the Tamiami Trail in 1928 opened up the region's enormous agricultural and resort potential.

During World War II hundreds of servicemen came to Naples and Collier County when the U.S. Army Air Field was built in 1943 to train pilots for combat over Europe and the Pacific. At the height of the war, several hundred men and 75 aircraft were assigned to the Naples base. Many of these officers remembered Naples when the war was over and brought their families to live in Naples.