# Large Villas in Chianti and Siena for 16+ Guests | Doorways > 10+ bedroom villas in Chianti and around Siena for family reunions and celebrations of 16 to 36 guests, personally inspected by Doorways Villa Vacations. Source: https://villavacations.com/travel-guide/large-villas-chianti-siena-16-guests/ 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. [Trip Inspiration](https://villavacations.com/category/trip-inspiration/) By [Susan Russo](https://villavacations.com/author/susan-russo1gmail-com/) · October 23, 2026 ![Large Villas in Chianti and Siena for 16 or More Guests](https://villavacations.com/wp-content/uploads/2026/06/villa-montosca-01-20240703_120420_2822jpg.jpg) For a group of 16 or more in [Chianti](https://villavacations.com/destinations/chianti/) or near [Siena](https://villavacations.com/destinations/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](https://villavacations.com/destinations/florence/) and Siena and in the countryside south of Siena. ## Ten bedrooms or more | Villa | Bedrooms / sleeps | Rate | Why we chose it | | --- | --- | --- | --- | | [Villa Collina](https://villavacations.com/villas/villa-collina/) Siena | 20 / 36 | Rates on request | A 13th-century estate near Siena with twenty en-suite bedrooms | | [La Poggiolaia](https://villavacations.com/villas/la-poggiolaia/) Chianti | 12 / 22 | From €16,250 / week | Five apartments above Certaldo, rented together, with a shared pool | | [Villa Montosca](https://villavacations.com/villas/villa-montosca/) Chianti | 10 / 20 | From €15,000 / week | Three buildings on six acres with views of medieval hill towns | | [Villa Benessere](https://villavacations.com/villas/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](https://villavacations.com/villas/villa-tavernaccia/) Chianti | 8 / 16 | From €32,000 / week | A Renaissance villa with an open-air theatre and views to Florence | | [Casa Bachicche](https://villavacations.com/villas/casa-bachicche/) Chianti | 8 / 16 | From €19,200 / week | A heated pool and private spa, fifteen minutes from Florence | | [Villa Chiara](https://villavacations.com/villas/villa-chiara/) Chianti | 8 / 16 | From €11,460 / week | An infinity pool and spa, halfway between Florence and Siena | | [Villa Cardinale](https://villavacations.com/villas/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](https://villavacations.com/italian-villa-rentals-faq/tuscany/), or see all [Chianti villas](https://villavacations.com/destinations/chianti/) and [Siena villas](https://villavacations.com/destinations/siena/). ## 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. 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