Already documented in the late 14th century, the villa belonged to the Segni family until the mid 18th century. It was originally called "Villa di Bellosguardo", from the name of the hill where it is located, but its name changed when its new owner, countess Teresa Spinelli Albizi, during the course of renovation in 1815, had a little iron pavilion in the Chinese style and in the shape of an "ombrellino" (small light umbrella) placed in the garden. In 1874, the property was purchased by the Zoubow family who united it with the adjoining Villa della Torricella, transforming the two gardens into a large romantic park abounding in exotic species including palms, bamboo, cedar and ginkgo biloba. In the first half of the 20th century, the portion of park that looks towards Florence was transformed into an Italian garden by British architect Cecil Pinsent.

The villa, which had numerous illustrious guests, was inhabited from 1617 to 1631 by Galileo Galilei who here wrote Il Saggiatore (The Assayer) and the Dialogo sui massimi sistemi (Dialogue Concerning the Chief World Systems), before moving to Arcetri. Galileo did not like to live in the city, and always lived between Bellosguardo and Arcetri. Between 1616 and 1617 at Bellosguardo, he performed a series of astronomical observations on the mean motions of the satellites of Jupiter (the Medicean planets) and elaborated the relative Tables. Together with Benedetto Castelli, he also observed the stars in the tail of the constellation of Ursa Major.

Inside the entrance loggia, a bust and commemorative plaque recall the great Pisan scientist’s sojourn. The villa has recently been restored, and hosts various events and a congress centre.