Tuscan villa

Try www.tuscany.net This site has a very good search function and good personal support if you're looking for recommendations. A friend of mine got a fabulous villa this way and had a great vacation.

I see a "villa" as a big old house you rent for just yourself. Owners don't live on the property. You have the whole place to yourself. We looked for a villa last year in prep for an Italian visit of about twelve of us this year. We found a few drawbacks:

1. Most villas only rent by the full week, Saturday to Saturday. If you only want 5 days, you're out of luck. If you want 10 days, you're out of luck. If you need to arrive on a Wednesday, too bad. So it kind of complicates your planning.

2. After a while we realized that if we commit to a villa that will hold all 12 of us, then some of the group end up canceling late into the planning (as indeed most of them did in our case), the remaining travelers could be stuck with paying for the whole place.

So we ended up staying at an agrituismo instead. At an agriturismo, the owner has broken the old family house, or an old barn on the property, up into several apartments for rent. The owner's family often live there too (it's a working farm), and there may be strangers in the apartment adjoining you. So an agriturimo can be very different from renting a whole villa for yourself.

We picked places that would hold all of us if we all were going, but each family rented their own accommodations so nobody risked being stuck with more than their own bill. Most places let you cancel with no charge until shortly before your visit.

At the agriturismo each family had an independent apartment with kitchen, so for meals there, one family could cook the meat, another would cook vegetables, another would make a salad, etc. then we'd all come together at a table on the patio at meal time. It was great.

Also, many agriturismos will rent by the night, or with a minimum of just 2 or 3 nights, and they're flexible on arrival/departure dates.
We did our searching at these places:

http://www.agriturismo.net/

http://en.agriturismo.it/

Steve,
Just two weeks ago, we spent five days in a wonderful apartment near Cortona, and very close to the Torontola train station, so we could travel into Florence without a car. It is called La Mucchia Casa Vacanze and is an 18th c. farmhouse that was lovingly brought back from ruin by the owners. It has eight apartments with one or two bedrooms. Ours had two, as we were two couples, and enjoyed cooking our own meals, etc. There's a pool, terraces and gardens, and near to stores to obtain provisions. We had a lovely time there, traveling to Florence by train, and via car to Cortona, San Gimignano, Pienza; Assisi and Orvieto are also easy day trips. Have a great trip!