Italian Villas for holidays with extended family.
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 with all the generations 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. Colle di Sotto
A villa and a cottage near Montelupo
A perfect spot for a family holiday.
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. Villa San Donato
Swimming pool, a village nearby and wonderful views.
Originally constructed in the 11th century as a watchtower along the renowned Via Francigena, this is a magical place to stay. The views over the owners own olive groves are beautiful, extending out over rolling hills and valleys. There is a small village nearby, close enough to walk to, and the house is perfectly placed to ast as a base for explorations of the Tuscan art cities, or as a relaxing, warm place to recharge.
The villa boasts terracotta flooring, exposed ceiling beams, and a grand fireplace, all adorned with elegant furnishings. Outside, guests can enjoy amenities such as a swimming pool, a vegetable garden available for guests, and an organic farm where olive oil is produced.
The caretaker resides in the farmhouse adjacent to the guests' villa, offering discreet assistance with requested services while ensuring that the guests' privacy is maintained.
Villa San Donato sounds fabulous!
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 23rd Oct 2025