It goes without saying that a big family holiday is the ultimate bonding experience. You’ll wake up to breakfast together, quality time by the pool and, if you’re in Tuscany or Umbria, a whole host of immersive experiences.
That said, a holiday with very young children requires a meticulous plan. If you’re on a multigenerational adventure – sometimes spanning as many as four generations – there’s the question of accessibility and other practicalities.
Our handpicked selection of family villas keeps these practicalities in mind. For one, they’re equipped with child-friendly swimming pools and other baby-proof amenities. With our complimentary concierge on hand at all hours, parents can organise a babysitter alongside tailored family activities.
Find the perfect family villa
If you want a family villa within walking distance of a village, or a private tennis court villa, there’s plenty to choose from. Our portfolio of large villas in Tuscany includes villas for rent with in-villa chefs, cinema rooms or hot tubs, with golf courses nearby and much more.
Sartomare
One for big family gatherings, Sartomare is exceptionally family-friendly, offering rooms with bunk beds and plenty of space for all generations to relax and reconnect. Children will love the dedicated playroom, complete with table tennis and table football.
The villa’s pizza-making parties are always a hit with younger guests, while the private tennis court and soccer field keep everyone active. Active families can make the most of e-mountain biking, horse riding and hiking in the stunning Maremma and Monte Argentario countryside.
Villa Cieli
Days are filled with culture, coastline and gelato stops with a stay at Villa Cieli, located within easy reach of Lucca and the Versilia beach clubs. This exquisite private villa sleeps up to 16 guests and is perfect for adventurous families thanks to its idyllic location.
Inside, expansive, light-filled living spaces create a relaxed setting for family life. Parents can unwind in the master suite, complete with a freestanding marble bathtub. Step out onto the private terrace for a quiet morning coffee before the day begins.
Venture outside to find a child-friendly swimming pool with a shallow beach entry for toddlers, and enjoy convivial family gatherings in the sun-kissed courtyard.
Borgo Fiore
Benefitting from three separate wings, Borgo Fiore is a family favourite. Its layout offers an exceptional level of privacy, allowing teenagers and couples alike to come and go as they please.
Meanwhile, the communal spaces have been designed with gathering and connection in mind. There’s also a spectacular private swimming pool that’s gated and secure.
The Villa Manager lives nearby, ready to assist with child-friendly menus, experiences and games – the list is endless.
Villa Astori
This beautiful Tuscan villa boasts a long list of family-friendly amenities. With multiple ensuite bedrooms and a separate guesthouse, there’s plenty of privacy for multi-generational groups.
A vast living room and spacious kitchen make it ideal for group gatherings and in-villa cooking classes. Outdoors, highlights include a large, secure swimming pool and table tennis facilities.
Families are assigned their own Concierge to handle every detail, from restaurant bookings to day trips.
Villa Denise
Ideally located for exploring the beaches of Versilia, Villa Denise is exceptionally family-friendly thanks to its size. The estate features a gated spring water swimming pool, shaded sunbeds, play areas, and a whirlpool zone.
There’s also a tennis court, football pitch and ping pong table – perfect for keeping everyone entertained.
Valdimora
This grand villa comes with flawless service, including an on-site concierge to handle every detail. Adults can unwind in the private spa, complete with a heated indoor pool, sauna and rainfall shower.
The concierge can arrange tailored wellness programmes, while toddlers can safely explore the large garden and play area.
Masseto al Bosco
This restored Tuscan farmhouse is ideal for families. Enjoy mornings by the heated pool, followed by tennis matches and breakfasts with fresh local produce.
Babysitters can be arranged, allowing adults to explore nearby Chianti vineyards. A separate guesthouse adds extra privacy.
Querciatello
Querciatello combines stylish interiors with family-friendly features. Child-safe gates and enclosed surroundings ensure peace of mind.
The private swimming pool, shaded pergola and concierge services make it easy to relax and enjoy a bespoke stay.
Villa Albizi
Villa Albizi simplifies family travel with its dedicated app, allowing guests to request services like fresh linen or meals.
Spacious living areas, a Family Suite and expansive gardens make it ideal for families with children.
Estate of Petroio
Spread across 650 acres in Chianti, this estate is ideal for large family gatherings. Two restored farmhouses offer elegant interiors and generous communal spaces.
Accessibility is thoughtfully considered, with ground-floor bedrooms for mobility-restricted guests. Two fenced pools and sports facilities make it perfect for children.
Contact our Villa Specialists
Discover our curated collection of family villas in Tuscany, Umbria and beyond. Our Villa Specialists can help you find the ideal villa, complete with child-friendly amenities and concierge services.
Each villa is unique. Whether you’re looking for a villa near a village or one close to golf courses, we can make it happen.