This is my 3rd trip to Tuscany, and so I know I am asking a question that others have called "the holy grail" of Tuscany villa search!

This time we are a larger group (4 couples), so my past research has not been useful. Plus a big stumbling block is that we need a Thursday to Thursday rental period, & many rentals won't accept that. (Even though I ask anyway!)

OUR TOP PRIORITIES:
1) an independent villa/farmhouse/agriturismo
2) within 20-30 minutes walk of a quaint town (my version of "quaint" = pedestrian streets, restaurants, a few shops)

Our last stay near Castellina was a perfect distance, but I don't think they are renting any more (Il Cerreto). I would do Castellina, Radda or Greve; or the area around San Quircio d'Orcia. . . oir anything my forum helpers can suggest that meets our top 2 priorities!

I've looked at over 40 rental agency sites, plus the usual Homeaway, AirBnB, etc. But no matter how much research I do, I know I'm missing a lot.

After much research & emailing owners, I have:
1) GREVE -near Montefiorelle: https://www.vrbo.com/663793 - but a bit more than some want to spend

2) GAIOLE: Casale Le Fonti: https://www.vrbo.com/879452 - perhaps too long a walk to a town that doesn't offer as much as others? I don't know this town...

3) CETONA - Il Vecchio Ulivo: www.homeaway.com/vacation-rental/p1908361 - I don't know if Cetona is the type of town we want, I've never been here

Any input on new places, or one of the 3 above is MOST welcome. Thank you in advance!

I haven't stayed in a villa before so unaware of their rental commitments, but spent a few nights in an agriturismo (La Crociona) outside Montalcino this September - I think most agriturismos would be flexible with your accommodation needs.
Since you've spent time in the Chianti area before, I'd seriously consider Val D'Orcia this time around. Does it have to be walking distance to a town, I suppose you will need and have a car anyway. I had also considered Fonte Bertusi and Cretaiole near Pienza, which receive favorable mentions.

Try this lovely little village https://www.chianti.com/barberino-val-d-elsa/. You might find something there.

Friends have stayed in this one and loved it .

http://www.bonomonte.com/en/hospital...e-san-bartolo/

Thank you Helsie. I was just looking at Barberino Val d'Elsa a few days ago! I like that it has a nice walking path to the next town, Tavarnelle Val d'Elsa.
I will check out Podere San Bartolo.