Travel & Destinations

Top Multi-Generational Vacation Rentals in Tuscany for Groups of 10 Plus

A curated selection of expansive agriturismos and historic farmhouses in Tuscany designed specifically for large, multi-generational groups. These properties offer ample private space, communal outdoor areas, and modern amenities to ensure comfortable and memorable family reunions.

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Il Borro Luxury Farmhouse

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Located within the exclusive Agriturismo Il Borro estate, this restored 15th-century farmhouse offers sprawling interiors and private gardens. It features multiple bedrooms, a professional kitchen, and access to the estate's Michelin-starred restaurant and spa services.

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Castello di Casole

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A historic castle converted into a luxury resort offering several large villa units within its grounds. Perfect for large groups, these residences provide private pools, expansive terraces, and exclusive access to the estate's championship golf course and renowned wine cellar.

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Poggio Scacciano

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An elegant restored farmhouse near Asciano that comfortably accommodates large families with its multiple wings and interconnected rooms. Features include a large communal living area, a swimming pool, and extensive grounds for children to play safely while enjoying Tuscan landscapes.

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Villa La Foce

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A historic country house set within a 300-acre estate, offering a blend of privacy and grandeur. The property features lush gardens, a swimming pool, and multiple seating areas, making it ideal for multi-generational gatherings who appreciate history and formal landscaping.

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Fattoria Il Prato

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A restored medieval farmhouse located in the heart of Chianti Classico, offering rustic charm with modern luxury. It features a large communal dining room, a swimming pool, and direct access to hiking trails, catering well to groups seeking both relaxation and cultural exploration.

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Castello di Velona

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Situated in the Val d'Orcia, this estate offers luxury farmhouses with stunning views of the iconic Tuscan hills. Each residence is equipped with private pools and large terraces, providing a serene environment for extended families while being close to Montalcino's wine estates.

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Borgo Santo Pietro

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A luxury resort offering independent villas within its historic estate grounds, ensuring privacy for large families. Guests enjoy access to the award-winning spa, gourmet dining, and organic gardens, creating a holistic and rejuvenating experience for multi-generational travelers.

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Agriturismo San Felice

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Part of the Tenuta di San Felice estate, this property offers traditional Tuscan farmhouses set among vineyards and olive groves. It provides a self-catering option with large communal spaces, wine tasting experiences, and proximity to Pienza and Montepulciano for cultural tours.

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Villa Le Fontanelle

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A restored 18th-century villa located in the Chianti region, offering expansive interiors and a large garden. It is ideal for large groups, featuring a swimming pool, outdoor barbecue areas, and easy access to Florence and Siena for day trips and cultural excursions.

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Castello di Brolio

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Home to the Barone Ricasoli winery, this historic castle offers luxury accommodations within its ancient walls. Guests enjoy private tours of the castle, wine tastings, and expansive grounds, providing a unique cultural immersion for families interested in Tuscan winemaking history.

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Fattoria di Maiano

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A beautiful farmhouse located in the Arezzo hills, offering panoramic views and spacious living areas. The property features a large swimming pool, garden, and traditional architecture, making it a peaceful retreat for large families seeking authenticity and relaxation in Tuscany.

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Villa Pizzofalcone

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Located near Siena, this historic villa offers modern comforts within a restored Tuscan setting. It features multiple bedrooms, a large garden, and a swimming pool, providing ample space for multi-generational groups to gather while being close to the city's cultural attractions.

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Borgo Egnaco

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A luxury resort in the Chianti Classico region offering private villas with stunning views. The property includes a golf course, spa, and fine dining options, ensuring that large groups have diverse activities available, from sports to culinary experiences, all within the estate.

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Tenuta di Biserno

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A prestigious estate in the Bolgheri area, offering luxury accommodations surrounded by vineyards and cypress trees. The property provides a secluded and elegant environment for large families, with access to gourmet dining, wine tastings, and guided tours of the estate's organic farms.

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Villa Castelnuovo Berardenga

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A historic villa located in the heart of the Chianti Classico zone, offering spacious interiors and beautiful gardens. It is well-suited for large groups, featuring a swimming pool, outdoor dining areas, and proximity to local wineries and medieval villages for exploration.

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Fattoria di Corsignano

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A restored farmhouse located in the Val d'Orcia, offering panoramic views of the surrounding hills. The property features a large communal area, a swimming pool, and rustic charm, making it an ideal base for families to explore the scenic landscape and nearby thermal baths.

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Castello di Querceto

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A luxury farmhouse within the Querceto estate, known for its organic farming and wine production. Guests enjoy privacy and exclusivity, with access to the estate's olive oil and wine, as well as beautiful grounds for relaxation and outdoor activities for children and adults alike.

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Villa Il Sorriso

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A charming villa located near Siena, offering modern amenities within a traditional Tuscan setting. It features a large garden, swimming pool, and spacious living areas, providing a comfortable and welcoming environment for multi-generational groups seeking a blend of luxury and local culture.

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Agriturismo La Foce

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While distinct from Villa La Foce, this agriturismo offers a more rustic and authentic experience in the same region. It provides large family-friendly rooms, home-cooked meals, and access to the estate's park, making it a budget-conscious yet charming option for larger groups.

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Borgo Santo Pietro Villa

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Offering standalone luxury villas within the Santo Pietro estate, this option ensures complete privacy for large families. The villas feature private pools, chef services, and access to the estate's extensive grounds, combining high-end comfort with the tranquility of the Tuscan countryside.