--- title: 'Five best Multigenerational Family Villas' url: 'https://invitationtotuscany.com/guide/five-best-multigenerational-family-villas' markdown: 'https://invitationtotuscany.com/guide/five-best-multigenerational-family-villas.md' lang: en date: '2025-10-23' description: "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 Docciole - Family Villa in Chianti, TuscanyThis is a large old stone farmhouse in Chianti, a classic Tuscan villa. It was converted by the owners, who normally live in Rome, to be their 'multi-generational family country retreat' and they put a lot of thought into what makes a family get-together work, including recognising that sometimes we all need a little 'alone' time. For this reason the lower floor bedrooms are all set up as little independent suites, with their own bathrooms and little kitchens - if you want to have breakfast alone, then this house is set up for that. 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. Radda in ChiantiLastly, it is within walking distance (half a mile) of Radda in Chianti, the self proclaimed capital of the Chianti region of Tuscany. There are restaurants, shops and most importantly, ice-creams in Radda, all without having to get everybody in a car. 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!. Show me Docciole! 2. Colle di Sotto A villa and a cottage near Montelupo The views from the pool are fabulous Colle di Sotto sleeps 15 - or 17 if you use the sofa-bed - in a villa and a cottage, each with a pool. You get two pools, one with a hot-tub, amazing views, and both buildings have AC. Unwind by the twin pools shaded by olive trees, or venture out to discover nearby gems like Florence, Pisa, Siena, San Gimignano, and Vinci. Whether you’re enjoying a glass of wine at sunset or drifting in the pool, Colle di Sotto is a place where time seems to pause, the views captivate, and Tuscany feels uniquely yours. A perfect spot for a family holiday. Colle di Sotto sounds great 3. Dimora A sprawling one floor villa where every door opens onto the garden. Dimora Villa for 12 in Chianti, Tuscany, Italy This villa for 12 is set in the vineyards and olive groves of a large Chianti wine estate. The estate is run along strict bio-organic rules and when the Estate owner converted this villa he decided to make sure the house would be as ecological as he could make it, with solar panels for electricity and rainwater collection. This is a great choice if you're trying to green your holidays. 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 Family fun in the big pool at Valdambra 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. Valdambra Villa Valdambra in Tuscany" taxonomy: category: - Guide tag: - 'Villas in Tuscany' - Family - '5 Best Villas' area: - Italy - Tuscany - Siena - Valdorcia - Florence --- Since 1982: over 40 years' experience Google: 4.8 [Google: 4.8](https://www.google.com/search?q=Invitation+to+Tuscany+Ltd) [+44 (0)20 8444 9500](tel:+442084449500)| [Whatsapp: ](https://api.whatsapp.com/send?phone=447700164339) ![Five best Multigenerational Family Villas](https://invitationtotuscany.com/user/pages/03.guide/five-best-multigenerational-family-villas/Valdambra-cropped.jpg) [ Guide ](https://invitationtotuscany.com/guide) [ Five best multigenerational family villas ](https://invitationtotuscany.com/guide/five-best-multigenerational-family-villas) # Five best Multigenerational Family Villas ## - [Villas in Tuscany](https://invitationtotuscany.com/guide/tag:Villas%20in%20Tuscany) - [Family](https://invitationtotuscany.com/guide/tag:Family) - [5 Best Villas](https://invitationtotuscany.com/guide/tag:5%20Best%20Villas) #### Table of Contents - [Italian Villas for holidays with extended family.](#italian-villas-for-holida) - [1. Docciole](#1-docciole) - [By a village and with an enormous garden](#by-a-village-and-with-an-) - [2. Colle di Sotto](#2-colle-di-sotto) - [A villa and a cottage near Montelupo](#a-villa-and-a-cottage-nea) - [3. Dimora](#3-dimora) - [A sprawling one floor villa where every door opens onto the garden.](#a-sprawling-one-floor-vil) - [4. Villa San Donato](#4-villa-san-donato) - [Swimming pool, a village nearby and wonderful views.](#swimming-pool-a-village-n) - [5. Valdambra](#5-valdambra) - [A sprawling ex-farmhouse with 3 apartments and a great pool](#a-sprawling-ex-farmhouse-) ![author dan wrightson](https://invitationtotuscany.com/user/themes/tuscan/images/dan-wrightson.jpg "dan wrightson")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 --- ## 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](https://invitationtotuscany.com/villas/italy/tuscany/siena/docciole) ### By a village and with an enormous garden ![Docciole - Sleeps 12 in Chianti](https://invitationtotuscany.com/user/pages/03.guide/five-best-multigenerational-family-villas/docciole00007.jpg "Docciole - Family Villa in Chianti, Tuscany")Docciole - Family Villa in Chianti, Tuscany This is a large old stone farmhouse in Chianti, a classic Tuscan villa. It was converted by the owners, who normally live in Rome, to be their 'multi-generational family country retreat' and they put a lot of thought into what makes a family get-together work, including recognising that sometimes we all need a little 'alone' time. For this reason the lower floor bedrooms are all set up as little independent suites, with their own bathrooms and little kitchens - if you want to have breakfast alone, then this house is set up for that. 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. ![Radda in Chianti](https://invitationtotuscany.com/user/pages/03.guide/five-best-multigenerational-family-villas/radda-in-chianti.jpg "Radda in Chianti")Radda in Chianti Lastly, it is within walking distance (half a mile) of Radda in Chianti, the self proclaimed capital of the Chianti region of Tuscany. There are restaurants, shops and most importantly, ice-creams in Radda, all without having to get everybody in a car. 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!.* [Show me Docciole!](https://invitationtotuscany.com/villas/italy/tuscany/siena/docciole) ## [2. Colle di Sotto](https://invitationtotuscany.com/villas/italy/tuscany/florence/colle-di-sotto) ### A villa and a cottage near Montelupo ![colledisotto-pool00236](https://invitationtotuscany.com/user/pages/03.guide/five-best-multigenerational-family-villas/colledisotto-pool00236.jpg "The views from the pool are fabulous")The views from the pool are fabulous [The views from the pool are fabulous](https://invitationtotuscany.com/images/c/o/l/l/e/colledisotto-pool00236-1b444256.jpg) Colle di Sotto sleeps 15 - or 17 if you use the sofa-bed - in a villa and a cottage, each with a pool. You get two pools, one with a hot-tub, amazing views, and both buildings have AC. Unwind by the twin pools shaded by olive trees, or venture out to discover nearby gems like Florence, Pisa, Siena, San Gimignano, and Vinci. Whether you’re enjoying a glass of wine at sunset or drifting in the pool, Colle di Sotto is a place where time seems to pause, the views captivate, and Tuscany feels uniquely yours. A perfect spot for a family holiday. [Colle di Sotto sounds great](https://invitationtotuscany.com/villas/italy/tuscany/florence/colle-di-sotto) ## [3. Dimora](https://invitationtotuscany.com/villas/italy/tuscany/florence/dimora) ### A sprawling one floor villa where every door opens onto the garden. ![Dimora Villa for 12 in Chianti Vineyard](https://invitationtotuscany.com/user/pages/03.guide/five-best-multigenerational-family-villas/dimora.jpg "Dimora Villa for 12 in Chianti, Tuscany, Italy")Dimora Villa for 12 in Chianti, Tuscany, Italy [Dimora Villa for 12 in Chianti, Tuscany, Italy](https://invitationtotuscany.com/villas/italy/tuscany/florence/dimora) This villa for 12 is set in the vineyards and olive groves of a large Chianti wine estate. The estate is run along strict bio-organic rules and when the Estate owner converted this villa he decided to make sure the house would be as ecological as he could make it, with solar panels for electricity and rainwater collection. This is a great choice if you're trying to green your holidays. 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](https://invitationtotuscany.com/villas/italy/tuscany/florence/dimora) ## [4. Villa San Donato](https://invitationtotuscany.com/villas/italy/tuscany/florence/villa-san-donato) ### Swimming pool, a village nearby and wonderful views. [ ![villa-san-donato00018](https://invitationtotuscany.com/user/pages/03.guide/five-best-multigenerational-family-villas/villa-san-donato00018.jpg "The pool at San Donato")](https://invitationtotuscany.com/villas/italy/tuscany/florence/villa-san-donato) 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!](https://invitationtotuscany.com/villas/italy/tuscany/florence/villa-san-donato) ## [5. Valdambra](https://invitationtotuscany.com/villas/italy/tuscany/arezzo/valdambra) ### A sprawling ex-farmhouse with 3 apartments and a great pool ![Farmhouse Villa with a large private pool](https://invitationtotuscany.com/user/pages/03.guide/five-best-multigenerational-family-villas/Valdambra_35.jpg "Family fun in the big pool at Valdambra")Family fun in the big pool at Valdambra [Family fun in the big pool at Valdambra](https://invitationtotuscany.com/villas/italy/tuscany/arezzo/valdambra) 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. [Valdambra](https://invitationtotuscany.com/villas/italy/tuscany/arezzo/valdambra) ![Valdambra family villa for 10-16](https://invitationtotuscany.com/user/pages/03.guide/five-best-multigenerational-family-villas/Valdambra_02.jpg "Villa Valdambra in Tuscany")Villa Valdambra in Tuscany [Villa Valdambra in Tuscany](https://invitationtotuscany.com/villas/italy/tuscany/arezzo/valdambra) ![author dan wrightson](https://invitationtotuscany.com/user/themes/tuscan/images/dan-wrightson.jpg "dan wrightson")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 --- [ Previous Post](https://invitationtotuscany.com/guide/italy/september-villa-visits) [ Top of Page](#top) [Next Post ](https://invitationtotuscany.com/guide/italy/the-great-family-getaway) ### Contact Us ### UK: Head Office [ +44 (0)20 8444 9500](tel:+442084449500) [ info@invitationtotuscany.com](mailto:%7B%7B%20'info@invitationtotuscany.com'%7Csafe_email%20%7D%7D) All Payments are secured by - 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