We just got back from two wonderful months in Italy, thanks to Rick Steve's books it went with hardly a glitch and very inexpensively also.
We are now thinking about spending a month or so in a large villa or apartment so that our grown children and grandchildren can spend a week or so at a time. They couldn't all come together but with one family at a time we would only need three bedrooms and two baths plus a large kitchen. Don't know where to start looking so we thought we'd give this site a try because there always seems to be good advise.
Jerry and Stelly
Try this web site.
http://www.greve-in-chianti.com/
We found an apartment on it but I think they have villas as well. We really liked this area.
Jerry:
We have rented Il Palagio (www.infochianti.com) several times. It is a wonderful place and seems just what you are looking for. It is located just outside of Panzano (directly between Florence and Siena).
There are many great villas in Tuscany - just fire up the google machine and see what you find!
Have fun.
For a Tuscan owned and operated business with excellent properties you can also try Tuscany Rent Direct - they have over 300 properties on the site now and there are some really nice villas that will fit whole families, friends, and more.
They also have a pretty useful blog, with tons of articles on small towns, things to do, etc.
Tuscany Blog
Here is their villas page.
Jerry,
I've rented a lovely apartment overlooking Montepulciano.
Great prices and lovely views.
It's called Montorio...they have a variety of apartments.