Records indicate that José Caldez, who had operated a fishing rancho[Note 1] on the island, called it Josepha's when he sold it in 1833.

A local folk story, extant in at least two versions, tells of Gaspar kidnapping a Spanish princess, with whom he becomes enamored.

One version identifies the princess as Josefa, daughter of Martín de Mayorga, Viceroy of New Spain from 1779 to 1782, and indicates that her burial place of Useppa Island still bears her name in an altered form.

A 9-metre-tall (30-foot) conical shell midden with ramps is located on the west side of the island towards the southern end.

The southern end of the island may have grown by as much as 500 metres (1,600 feet) during the 20th century, possibly when a golf course was developed there.

Useppa Island is high ground that became separated from the mainland by a rising sea level around 4500 BCE.

[3][5] Before Useppa Island separated from the mainland, the area was visited by Paleo-Indians, who were present in Florida by at least 8,000 BCE.

Around 1784, Jose Caldez of Cuba began using Useppa Island as the base for his seasonal fishing operations.

Henry Crews, the U.S. Customs officer on Josefa Island (Useppa), was killed in late March 1836, possibly by Seminoles or by Indians working at the rancho.

The U.S. Army established Fort Casey on, renamed, Useppa Island early in 1850, but abandoned it before the end of the year.

Barron Collier bought the island in 1911, and developed the resort, enlarging the hotel and adding tennis courts and a 9-hole golf course.

In 1960, Useppa briefly served as a CIA training base for Cuban exiles in preparation for the Bay of Pigs Invasion.