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Recommendation for Tuscany House/Villa Rental for a large family?

We are planning a trip this summer (June 2023; a bit of a late revenge travel!) for our extended family of 6 adults and 3 kids. We want to find a house or villa to rent for our 4 days stay in the Tuscany area. We want to be close to either Florence or Siena, but plan to visit nearby hill towns, Pisa, Luca, etc.

We have looked at VRBO, AirBnB, and Bookings.com, and there are a lot of options. We wanted to see if any seasoned Italy travelers here have recommendation for:
1) an area or even a specific house/villa we should consider?
2) a more local agency we should work with?

Some of the considerations we have are:
- We will have a car, but don't want to be too far from restaurants/markets.
- Family friendly; our kids are ranged from 1 to 8.

Thanks in advance!

Posted by
1057 posts

A somewhat delayed response, but I have used Tuscany Now villa rental company with great success and will be staying in another of their villas this fall. They have plenty of places big enough for your family group. We stayed in Umbria, not Tuscany, at this incredible place. We loved the little town of San Gemini (no, NOT San Gimignano in Tuscany) and the nearby Roman ruins of Carsulae, formerly a very busy Roman market town and now barely visited by tourists.

You may have found something you like by now; my key advice is to look to see how far a villa is from a town or a few shops. It’s annoying to get in the car for 45 minutes down twisty roads every time you need something to eat.

Have a great trip!