Machiavelli Villa's compelling history dates back to the late 14th Century. The villa was built by the Machiavelli family and designed by Michelangelo, the famed Italian sculptor, painter, and architect of the High Renaissance. Because of the historical significance of the villa's owners and architects, the original buildings plan for improvements are housed at the Uffizi Gallery in Florence. These plans include a grander palace with a new wing, designed by Giorgio Vasari il Giovane. On the occasion of the marriage between the Machiavelli and Strozzi families, the coat of arms of the two families (Machiavelli/Strozzi) was affixed on the keystone of the central arch of the loggia on the main façade. The same emblem is present on the fireplace located on the ground floor of the villa. Niccolo Machiavelli wrote "The Prince" at his studio in Albergaccio, which was connected to Machiavelli Villa via an internal path.

In 1646, the Machiavelli family sold the Villa and the ownership was turned over to the distinguished aristocratic family of Mazzei. Filipo Mazzei, an Italian physician and a promoter of liberty, was a close friend of the 3rd US president Thomas Jefferson. The Mazzei family was the longest serving owner of the villa, spanning over three centuries until the mid 20th century, with 1956 marking the end of many generations of the Mazzei dynasty's ownership of the Machiavelli estate. Machiavelli Villa was sold to Guidi da Bagno, whose origins are from an ancient noble family. Bagno held the property for only two decades. During this period the ruins from the WWII bombing of the East wing were removed and the front entrance and piazza were modified.

In 2001, the property was sold to the current owners, investing in a multi-million dollar renovation, restoring the villa to its former splendour. During 2007, the restoration was completed and the villa was opened as a Small Luxury Hotel. The classic beauty of Machiavelli Villa combined with its art and idyllic Tuscan setting guarantees a brush with the historic past. At Machiavelli Villa you will find modern day conveniences are seamlessly combined with the splendor of the Renaissance.