Staffed villas in Chianti, from castles to palazzi
The great houses of Chianti were always run by people who knew them: the cook who understood the wood oven, the housekeeper who kept the keys to the cellar. A staffed villa keeps that tradition alive. Meals follow the season and the market, the table is laid on the terrace without anyone asking, and the family on holiday faces nothing more demanding than choosing the wine.
The 32 villas below have a cook, a butler or staff living on site, and several are houses of real history. One is a 15th century castle in an 8 hectare walled park of sequoias and cedars of Lebanon, with a consecrated chapel; another was built in 1854 by the Hohenlohe Waldenburg princes, within a 1,100 hectare wine estate; a third was the summer house of Salvatore and Wanda Ferragamo, with original frescoes and a private chapel.
At a glance
- 32 private villas
- From 2 to 20 bedrooms
- Up to 38 guests in one villa
- 32 with a private pool
- 32 with a cook or staff
- Availability and price on request, reply within one working day
Ribollita, pappa al pomodoro, pici with ragù and bistecca cooked over wood: a local cook will build the week around what is in season.
On one medieval estate near Castellina a Chianti Classico cellar lies directly below the palazzo, so a tasting needs only a staircase.
Breakfast only, lunch and dinner, or a butler throughout: each house differs, and we set out exactly what is included before you confirm.
Choose your villa
Add up to five villas to your list and send one request with your dates: we confirm availability and price with each owner.
























Show all 32 villas








Positions are approximate: the exact address is shared once your stay is confirmed.
Questions before you choose
What does staff on site mean?
It varies: a cook, a butler, or a caretaker and housekeeper living on the estate. Each listing states what is included, and we confirm hours, days and any extra charges with the owner.
Is there a driver or transfer service?
Not usually as standard, but owners can often recommend trusted local drivers. Florence airport is under 1 hour 15 minutes from most Chianti villas, and we pass on transfer options with our reply.
Can we book a staffed villa for a short stay?
Sometimes, outside the peak weeks of July and August. Send your dates for up to five villas in one enquiry, and we reply within one working day with availability, price and the service each offers.
- Summer in Chianti from a villa among the vines
- Easter in Chianti, in a villa of your own
- Autumn in Chianti, a villa for the harvest
- Christmas in Chianti, by the fire in your own villa
- Wedding villas in Chianti among vineyards and olives
- Family villas in Chianti, with room to roam
- Large villas in Chianti for groups of family and friends
- Chianti villas with a private pool above the vines
- Staffed villas on the Amalfi Coast
- Staffed villas in Sorrento
- Capri villas with a cook, butler or staff
- Staffed villas in Tuscany, with a cook or butler
- Umbria villas with staff, the house looked after
- Staffed villas in Puglia, the masseria kept for you
- Staffed villas on Lake Como, with a cook in house
- Sicily villas with staff and a private cook