Ciao Tom and welcome to our forum!
That sounds like an awesome trip! Now, your choices are very wide if all you really need is a pool and walking distance to a (good) restaurant
. You could either decide to stay in one place for the 2 weeks or divide it up into 2, if this is your first time in Tuscany I'd say divide it into 2 places and the first week stay closer to area further up, closer to Florence - you could visit the coast, Pisa, Lucca, San Miniato, San Gimignano, areas of Chianti, Florence, of course!
The second week stay in the area of the Val d'Orcia, south of Siena and visit Siena, Volterra, the wine town of Montalcino and Montepulciano, San Quirico, Pienza, the hot springs at San Filippo and Bagno Vignoni.
Ok so suggestions for the first week:
Viticcio outside of Greve in Chianti - close enough to town, it's a winery so you can also enjoy tastings and winery tour. Read
our review here.
Villa Le Torri - this is divided into apartments, close to a small town with a restaurant or two. Here is
my review.
These two are pretty central, there are a lot others I'm thinking of that are not too close to town, but as you will have a car maybe you want you'd like those too? Let me know.
As for south of Siena, I'd recommend Podere Cunina, which is close enough to Buonconvento for a walk but also on top a hill, with great views. So you might want to take the car anyways if you want to avoid the climb uphill on the way back. Here's
my review. They do cooking classes which I'd recommend!
Another two to look at - Sarna Residence and Villa San Fabiano - you can find those and more on this page:
Val d'Orcia Accommodation: find the perfect rental for your vacation in Val d'Orcia,Tuscany. Book your holiday accommodation directly with the owners!
www.tuscanyaccommodation.com
Ok let me know what you think of these options, and what you like.... that way I can offer more specific ideas if these are not what you're looking for.
