Need Villa for 11 People in Siena Area

As an aside - many or most of the villas in Tuscany are out in the countryside, and for
11 people, you'd need at least 2 cars/vans to get everyone around in, unless you can
rent a Mercedes Sprinter or something like that.

I don’t have suggestions for specific villa or agriturismo (farmhouse converted to villa).
I suggest checking the following websites which have plenty of choices in Tuscany.
www.agriturismo.com
www.agriturismo.it
www.agriturismo.net
www.agriturismi.it
www.agriturismtaliani.it
and also www.vrbo.com, www.holidu.com

As mentioned in the previous comment, nearly all will require private transportation to reach, as they tend to be in secluded country locations not served by public transit of any type.

For 11 people you will need at least 3 station wagons or large cars. You could rent two vans, but each van is likely more expensive to rent than 3 cars. Also vans are not easy to maneuver in the narrow Italian streets.

A Mercedes Sprinter Van or any van holding more than 8 pax plus the driver requires a D1 type of license in the EU. The D1 license is a mini bus driving license for vans (or minibuses) with more than 9 passengers but no more than 16, which is what you require for 11 people.unless someone in your party has a bus license, that is not an option for you, and I wouldn’t suggest to anybody to rent a vehicle that large in Italy, unless you are a professional bus driver.

Check your options:
www.autoeurope.com

hey hey pochola430
looking for a villa to fit your family may be tough but roberto give options for you to look at. you will need a bigger van as he mentions or 3 cars for all of you if you want to stay that offers parking (free or a fee) since they are out in the countryside with transportation being a hard sell for all of you. make sure all drivers have an IDP (aaa.com/IDP) along with drivers license, it is mandatory in italy. read all about driving, laws, rules, ZTL's, parking, road conditons, maps of area, space for people and luggage, pack light and is there a washer/dryer available. lots to think about.
where are the markets at to buy supplies needed for kitchen.
discovertuscany.com
tuscany is a big area to look at within the florence area. glad you're looking ahead of time since may can be a busy time, many travelers to italy nowdays and it's high season. when you find what suits your gang book it. then decide on attractions/activities. where will you fly into and out of. check-in times are usually 3-4pm and check-out times are 10-11am. look at all necessities you need, are linens included or need to pay for them, can you check in early or pay an extra day if arriving early. ask you hostess/host. what is included, what month is pool open if an important issue. ask about kitchen, outdoor dining you need.
good luck, enjoy and happy hunting
aloha

Yes

https://www.rentbyowner.com/property/la-villa-di-primo/BC-1419682

My family and I took this villa for a week.

https://www.castellodimodanella.it/

Quintessential location for a wedding. Popular with Australians.

Regards Ron

I've used this English company twice with good results both times: Tuscany Now and More. They're not a very big outfit but were very responsive. They have exclusive listings of the villas they represent, see if you find anything you like.