Steven- I am not sure if this will meet the definition of a villa, but we rented a very nice 2 bedroom apartment in Greve-In-Chianti last September that we loved. The place was called Casa Nova and it was within walking distance of Greve. Greve is a medium size town with shops, restaurants, a grocery store and a wonderful Saturday market. From there, you can catch a bus north to Florence or South to Siena (it takes about an hour to get to either city) Of course, the bus goes through some other villages in Tuscany on the way that you could explore.) The TI in town can also arrange some tours (wine tasting, castle exploring, etc.) where transportation is included. In addition, when you arrive in Florence, the bus station is right next to the train station and you could use public transportation to get to many other near by areas. Our apartment was in the hills of Chianti nestled in among the grape vines. It was quite large (my husband estimates over 1000 square feet). It had a full kitchen and an nice picnic table to enjoy outdoor meals. Breakfast was not included, but the owner provided us with coffee, juice, jam, tea, etc. We absolutely loved our time there. We took several nice walks up through the vineyards for some jaw dropping views. You might look at this web site for more information about Greve http://www.greve-in-chianti.com/ and this site for more infomation on Casa Nova http://www.casanova-laripintura.it/en/casanova.htm The first web site lists many acomnodations in the area, but be careful that you choose one with in walking distance of Greve. Also, we were there in September and having a pool or air conditioning might be important to you. I'm not sure our apartment had air conditioning and we did not have a pool.