Italian Villas for Extended family holidays
Tuscany is always wonderful place to take the family on holiday - there is plenty to do and explore for all ages, and swimming pools for when the exploration is done. But it need not just be parents and children: a recent study found that seven in ten families have chosen to holiday together, from kids to grandparents.
We are big fans of the multi-generational holiday, when the whole family goes together. It's a great time to reconnect, enjoy some time together and give the grandparents some quality time with the little ones. And perhaps give the parents a little downtime too.
We've seen a big rise in these kind of holidays in the recent years and have a selection of large family villas that suit this kind of family gathering. Here are our best five multigenerational family villas in Tuscany:
1. Docciole
By a village and with an enormous garden

Conversely, when you are all together, eating and cooking are great social occasions, so the upstairs living room and kitchen are enormous, perfect for large meals together. In summer, Tuscan life moves outdoors, so there is also an outside kitchen, including a fabulous "Heath Robinson-like" clockwork barbecue, set next to an table under a pergola clad in vine leaves.
The last review, from UK clients:
"We absolutely loved our time at Docciole. You will be welcomed by lovely Anna who’s family home it is. It is a typical Tuscan stone farmhouse with a lovely homely feeling and loads of space for living inside and out. We particularly enjoyed the outdoor kitchen under a grape vine pergola and the swimming pool surrounded by olive trees. It is exceptionally well equipped for cooking and eating Anna is a perfect host and responded to the small issues that cropped up. It is a short walk to charming Radda in Chianti with spectacular views across Tuscan countryside, some tourist shops and a useful Coop supermarket. It is perfectly situated to explore the Chianti region if you’re into wine, medieval villages or the spectacular Sienna and Florence. Can’t recommend it highly enough!.
2. Pietrina
A family villa near Arezzo and Cortona
This is a review from guests in 2021:
"We spent a wonderful time at Pietrina that is situated in a very panoramic position close to San Giustino Valdarno. [...] There is a lovely terrace on the front side of the house with a generous BBQ station from which you can look at the ample olive grove and the Pratomagno with its heights and woods and another place where to eat and dine under magnificent old oaks looking to the other side, the hills and fields of the Arno valley. Not to forget the sumptuous pool area with enough space to be able to play crocket or KUP (our passion). All this is beautifully arranged with lots of flowerbeds gradually ascending versus the woods. [...] The situation at the end of a little valley makes Pietrina a very peaceful retreat, sometimes you will see at dusk some boars coming down to the olive grove, a tame fox showed up asking for a goodie which we refused of course because it has to learn to survive in the wilderness. However, it was extremely sweet. A lasting impression is that this is a very natural and authentic neighbourhood (the next neighbours are not very far away). In fact, we got to love this region that seemed to us not at all as touristy as the Chianti or Crete Senesi and offering a great quality of life. Arezzo is stunning and Florence is not too far to visit for a day.
A perfect spot for a family holiday.
Pietrina sounds perfect for us
3. Dimora
A sprawling one floor villa where every door opens onto the garden.
It's also a great choice if you love wine - you can buy the excellent wine produced by vines a few feet from your door and the owner will give you a guided tour of his wonderful cellars in nearby Barberino Val d'Elsa.
Like Docciole, this house also has a fabulous barbecue and lots of spaces for outdoor living, playing and dining.
Famous wine estate? Dimora it is
4. Amorosa
Swimming pool, Tennis court and endless views.
Villa Amorosa is on the edge of the "Riserva di Berignone", an area of over 2,000 hectares (around 5,000 acres) of hills covered in dark holm oaks, with streams, caves, castles and long paths hidden within. This gives the house fabulous views and, for the more adventurous, amazing possibilities for exploring. If you drive to the end of the track that goes past Amorosa, you will find an old house and the road barred. Leave the car and walk from here - not too distant is an old Castle, once owned by the Bishops of Volterra, set on a cliff over the river Sellate.
If you prefer to simply enjoy the view the house has a wonderful fenced pool, a tennis court, a children's playground and a ping-pong table. A perfect villa for relaxing family holidays.
Far from the crowds, perfect! show me Amorosa
5. Valdambra
A sprawling ex-farmhouse with 3 apartments and a great pool
The owner of this beautiful old farmhouse converted it carefully into three apartments that work very well when taken altogether as one big house. There are hammocks among the trees, corners to relax in, wonderful restaurants and places to explore nearby this villa that seems designed to slow down our busy lives.
Arezzo and Siena are both within easy reach, as are smaller hill villages like Civitella in Val di Chiana, or Monterchi.


Author: Dan Wrightson
Dan Wrightson grew up in Tuscany, Italy and has been writing about, sketching and exploring Tuscany and Italy since 1983.
19th Dec 2018 4th Nov 2024