Family Villas Tuscany
Suggested Family Villas in Tuscany
Tuscany’s rolling hills, sun-drenched vineyards, and charming medieval towns make it one of the most picturesque and sought-after regions in Italy. Whether you’re planning a family vacation, a reunion, or a milestone celebration, finding the perfect villa can transform your stay into an unforgettable experience. Here are some of our top picks for family-friendly villas in Tuscany:
- Sleeps: 10, up to 15 with guest house
- Location: Near Cortona
- Highlights: This beautifully restored olive press offers spacious accommodations ideal for families. Enjoy its rustic charm, large pool, and proximity to Cortona’s historic town center.
- More Info: Antico Frantoio Villa https://classicvillavacations.com/collections/villas-in-tuscany/products/antico-frantoio-sleeps-10-up-to-15-with-guest-house
- Sleeps: Up to 18
- Location: Val d’Orcia
- Highlights: Surrounded by iconic Tuscan landscapes, this luxurious villa is perfect for large groups. Relax in the expansive outdoor spaces or explore nearby Pienza and Montepulciano.
- More Info: [Casa Cote Sud Villa https://classicvillavacations.com/collections/villas-in-tuscany/products/casa-cote-sud
- Sleeps: Up to 16
- Location: Chianti
- Highlights: Nestled in the heart of the Chianti wine region, this villa is ideal for large families or groups. Enjoy wine tastings, outdoor dining, and stunning vineyard views.
- More Info: CentoCinquanta Villa https://classicvillavacations.com/collections/villas-in-tuscany/products/centocinquanta-luxury-villa-in-chianti-sleeps-up-to-16
- Sleeps: Ideal for multi-generational families
- Location: Chianti
- Highlights: Located on an active wine estate, this villa offers a blend of luxury and authenticity. It’s a fantastic choice for families looking to enjoy wine tours and Tuscan cuisine.
- More Info: CentoTrentauno Villa https://classicvillavacations.com/collections/villas-in-tuscany/products/centotrentouno
- Sleeps: Up to 25
- Location: Agriturismo
- Highlights: Perfect for large family reunions, this stunning agriturismo features separate areas for individual family groups, a large pool, and breathtaking countryside views.
- More Info: Podere Vittorio https://classicvillavacations.com/collections/villas-in-tuscany/products/podere-vittorio-beautiful-agriturismo-sleeps-up-to-25
Plan Your Tuscan Getaway
Each of these villas offers something unique for families, whether you’re seeking tranquility, adventure, or a mix of both. With plenty of space, modern amenities, and authentic Tuscan charm, these properties are perfect for making memories that will last a lifetime.
Contact us today to find the perfect villa for your family trip to Tuscany! info@classicvacationrental.com
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Tuscany is full of dreamy landscapes, historic towns, and unforgettable food and wine—but choosing the right area to stay in can make all the difference. From the central convenience of Chianti, to the cinematic hills of the Val d’Orcia the coastal charm of Lucca, and the elegance of Cortona—here’s how to choose the best base for your Tuscan adventure.

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So many women, so many stories. My journey to find unique and special properties introduced me to these extraordinary women and their ventures. I want the women of Canada and the USA to experience Italy and find a way to bring Italy home.
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Women traveling solo or in groups has become a well-documented trend. More women than ever are choosing to travel alone or with friends, sisters, mothers, or book clubs—whether to celebrate a milestone birthday, heal from a personal loss, achieve a long-held dream, or simply take a well-earned break from daily life.

Explore Italy's Most Stunning Train Journeys: A Perfect Villa Escape Add-On
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Italy is a country of endless beauty, where every corner offers a story, a flavor, or a view that takes your breath away. While staying in a charming villa offers the perfect base to immerse yourself in la dolce vita, adding a scenic train journey to your itinerary can elevate your Italian experience even further.
In a recent article by AFAR, some of the most picturesque train rides in Italy were highlighted, showcasing routes that take you through dramatic coastlines, rolling countryside, and even across to Sicily. Here are a few highlights to inspire your next trip: