Villa in Tuscany

I've been looking for a large airbnb/homeaway for 8-10 people, also (for June). Found a couple nearish Florence and some other smaller towns, but not quite the perfect set up, in terms of double beds for couples and at least 2 bathrooms. I'm still on the hunt. Perhaps you'll find the perfect one and share!

Booking.com has taken over Villas.com I believe. Also see VillasofDistinction.com I'd be looking for the area south of Florence in Tuscany.
Your group has enough people where you might can find a great Italian cook to do your nightly meals. And the incredible Brunello di Montalcino wines could top it off.

We have used www.tuscanynowandmore.com twice. Almost all of their properties appear terrific. The first property with a view of Montepulciano was awesome. The second included an "upgraded kitchen." Only the dishwasher was new - and it broke. The stove top had just three working burners. It also advertised a heated pool that, in the end, we were required to pay for the heat. Caveat emptor.

We had a wonderful experience renting a villa from Chianti and More in Panzano. They have villas of all sizes in the Chianti region and apartments in Florence. The listings on their website are exclusive to their agency.

We used www.hilltowntours.com. They provided great service and have beautiful villas.

Thanks for the sites to check for a Tuscan villa. The group of 10 want to be near Assisi and Cortona. I'll check out the sites mentioned above.

We're looking for five bedrooms each with ensuite baths for late April 2020. Not too far from main roads, maybe even reachable by our rental car to local train station to get to towns for the day. Would be good to have Pool, outdoor eating areas, renovated kitchen, smaller private areas as well for quiet time, journaling, etc. any ideas?

Thanks, everyone.

One thing to think about, if you want a pool, is that they may not be heated.
Also, you have to think about what altitude your villa will be at; as if it is high in the hills, it may get quite cool at night, and so the pool might not be very comfy to use for the same reason.
We rented what we thought was a perfect villa near Arezzo one year, brought pool toys etc with us; and then could hardly use the pool as it was such icy water!
It never warmed up, and we actually built a fire in the indoor fireplace every night.
When we got back down to Rome, we were sweltering hot.
It was mid September.
Just something to consider; as it never occurred to us to look at what altitude the villa was at.

Try looking in Castiglione del Largo or around the larger town of Perugia. These two locations will put you almost equidistant from Cortona and Assisi.

When using booking.com, for a large group, you might need to set your filters for more people to get the bed setup you desire.

We stayed at a hilltop villa two years ago that has everything you‘re listing...6 bedrooms with own bathrooms, pool, updated kitchens, outdoor eating area, indoor gathering places...except for one thing. It‘s in Umbria, rather than Tuscany. It is close to Assisi and quite easy to get from there to a number of lovely hill towns in Umbria and Tuscany, including Cortona. One of the things that I loved about the place is that we had a view from our hilltop across a valley to Assisi. The pool is unheated, so my guess is that it would be a bit cold for a dip in April. The web address for La Montagnola is http://www.agriturismo-lamontagnola.it/en/ . The six bedroom house on the hilltop is called Caprareccia. It’s actually divided into two independent three bedroom apartments, but can be rented as a whole. There were seven of us when we rented the whole house. It’s a wonderful house and beautiful property. They produce really good olive oil. You can arrange to have a cooking class for your group in the gorgeous family estate house on the property. While the food is cooking, they’ll take you on a tour of the olive oil making operations. It’s off the beaten path just enough that the price is very reasonable.