Villa di Castiglioni

In the rolling hills surrounding the village of Montespertoli, at the heart of the Chianti wine region, Villa di Castiglioni stands at the centre of an aristocratic Florentine estate whose history stretches back to the year 1100. The same family has owned the Tenuta di Castiglioni for nearly a millennium — and still does today, retreating here regularly from Florence as generations before them have always done. To stay at Villa di Castiglioni is therefore something genuinely rare in the world of luxury villa rentals: an invitation into a living family home of extraordinary historic depth, shared with a privileged few.
The 17th-century villa is as beautiful inside as its setting suggests. High ceilings, vast sitting rooms, a grand stairwell, and garden-facing sleeping quarters set an atmosphere of quiet grandeur throughout, while family portraits, paintings, and prints adorn the walls — each room following its own considered colour scheme, the whole suffused with the warm Tuscan light that pours through numerous glass doors and windows from morning to evening. Five ensuite suites accommodate up to 10 guests: two on the ground floor with direct access to the outdoor dining terrace and gardens, and three upstairs with open views over the hills and fields of Chianti. The ensuite bathrooms were fully restored in 2019, and a new lift now connects the two floors with ease.
Castiglioni's own cleaning and kitchen staff accompany guests throughout every stay, ensuring that every practical need is met with warmth and discretion — leaving guests free to simply enjoy one of Tuscany's most remarkable and historically resonant homes.
Villa di Castiglioni is a Chianti villa rental of genuine historic distinction — a place where nearly a thousand years of history settles around you as naturally and warmly as the Tuscan sunshine.