Chianti and Siena
Large Villas in Chianti and Siena for 16 or More Guests
Estates with 8 to 20 bedrooms in the wine country between Florence and Siena, each one personally inspected by Doorways.
For a group of 16 or more in Chianti or near Siena, the largest villas are historic estates with 10 to 20 bedrooms, and a few farmhouses with eight. Doorways Villa Vacations, an Italian villa specialist since 1994, has personally inspected every one below. They sleep from 16 to 36 guests, between Florence and Siena and in the countryside south of Siena.
Ten bedrooms or more
| Villa | Bedrooms / sleeps | Rate | Why we chose it |
|---|---|---|---|
| Villa Collina Siena |
20 / 36 | Rates on request | A 13th-century estate near Siena with twenty en-suite bedrooms |
| La Poggiolaia Chianti |
12 / 22 | From €16,250 / week | Five apartments above Certaldo, rented together, with a shared pool |
| Villa Montosca Chianti |
10 / 20 | From €15,000 / week | Three buildings on six acres with views of medieval hill towns |
| Villa Benessere Siena |
10 / 20 | From €21,191 / week | Staffed, between the Val di Chiana and the Val d'Orcia |
Eight bedrooms, sleeping 16
| Villa | Bedrooms / sleeps | Rate | Why we chose it |
|---|---|---|---|
| Villa Tavernaccia Chianti |
8 / 16 | From €32,000 / week | A Renaissance villa with an open-air theatre and views to Florence |
| Casa Bachicche Chianti |
8 / 16 | From €19,200 / week | A heated pool and private spa, fifteen minutes from Florence |
| Villa Chiara Chianti |
8 / 16 | From €11,460 / week | An infinity pool and spa, halfway between Florence and Siena |
| Villa Cardinale Siena |
8 / 16 | From €32,000 / week | A former country residence of aristocratic families, near Siena |
Getting around
You will want a car or a private driver: Chianti villas sit at the end of country lanes. Read our Tuscany FAQ, or see all Chianti villas and Siena villas.
Frequently asked questions
Which villas in Chianti have 10 or more bedrooms?
Doorways Villa Vacations offers La Poggiolaia above Certaldo (12 bedrooms, sleeps 22) and Villa Montosca (10 bedrooms, sleeps 20). Near Siena, Villa Collina has 20 bedrooms and sleeps 36, and Villa Benessere has 10 and sleeps 20.
Can 20 people stay together in one villa in Chianti?
Yes. La Poggiolaia sleeps 22 across five apartments on one estate, and Villa Montosca sleeps 20 in three buildings on six acres. Book a summer week about a year ahead.
