Imagine waking to sweeping views of rolling vineyards, where the first thing you see is sunlit rows of vines stretching to the horizon. Staying in a villa on a working vineyard offers more than just a holiday; it’s an immersion into Tuscany’s wine culture, with tastings on your doorstep.
From the renowned Chianti hills, home to the world-famous Chianti Classico, to other prestigious wine-producing areas, our villas on vineyards place you at the heart of Tuscany’s winemaking tradition. Whether you want a touch of luxury or a converted farmhouse on wine estates, guests can enjoy tastings and trails through the vines that have inspired centuries of wine production.
To Tuscany offers the best villas in vineyards for wine lovers and those seeking an authentic taste of Tuscany.
The Best Villas in Vineyards in Tuscany
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Villa Agresto
6 bedrooms, 5 bathrooms | Private Pool
Agresto sits on its private hilltop, offering 360-degree vineyard views. This secluded retreat in the Chianti hills of Siena is just 2.5km from the heart of the Ricasoli estate, which offers castle tours, wine tastings, a bar, and a first-class restaurant. The Ricasoli family has been producing wine on the estate for 800 years, with the current Baron Ricasoli still residing in the nearby Brolio Castle. Agresto is a great place to relax and explore the historic wine-making region of Tuscany.
https://www.to-tuscany.com/villaagresto/ -
Villa Bernardi
5 bedrooms, 4 bathrooms | Private Pool
Villa Bernardi is a beautiful and spacious Tuscan holiday home just 3km from the charming town of Panzano in Chianti. This carefully restored 11th-century property has an on-site winery, which is available for wine tastings. Villa Bernardi is an excellent place for large families or group of friends looking to reconnect and indulge in the luxury of the Chianti wine-making region.
https://www.to-tuscany.com/villabernardi/ -
Villa Vinsantaia
2 bedrooms, 2 bathrooms | Private Pool
Relax and unwind at Villa Vinsantaia in the heart of Tuscany's renowned Chianti Classico wine region. Guests can enjoy unparalleled vineyard views from the villa's infinity poolside terrace before taking a leisurely stroll to the local winery, where wine tastings await. The villa is also ideally located for day trips to cultural gems such as Siena and San Gimignano, enriching your Tuscan experience.
https://www.to-tuscany.com/villavinsantaia/ -
Villa dei Cavalli
4 bedrooms, 4 bathrooms | Private Pool
Set on a small wine-producing estate in the upper Valdarno Valley countryside, halfway between Florence and Arezzo, Villa dei Cavalli is the perfect oasis amongst vineyards. Guests can enjoy daily walks through the vineyards, where the pool sits in its own secret hideaway, creating the perfect escape from daily life. The villa sits on a tranquil estate that produces its own oil and wine, with wine tastings available to be arranged on-site and local produce available to be bought directly.
https://www.to-tuscany.com/villadeicavalli/ -
Casa Villa
10 bedrooms, 8 bathrooms | Private Pool
If you are looking for a large villa big enough for a party of 20 in the countryside just outside Florence, look no further than Casa Villa. The villa sits on the Torre a Cona estate, where you can treat your guests to wine tastings and fine dining. The estate's famous Torre a Cona winery has been recognised in the awards known as 'I Tre Bicchieri' (The Three Glasses) and is included in the Vini d'Italia Gambero Rosso Guide 2025.
https://www.to-tuscany.com/casavilla/ -
Casa di Pesa
2 bedrooms, 2 bathrooms | Private Pool
Casa di Pesa is a charming Chianti holiday home set on the Carma wine estate with easy access to the region’s renowned wineries, castles, and historic towns such as Siena, San Gimignano, Florence, and Radda in Chianti, ideal for day trips. This stone house is divided into two separate apartments with private entrances, making it suitable for couples travelling together while enjoying their space.
https://www.to-tuscany.com/casadipesa/ -
Need further inspiration? To Tuscany’s entire villa collection promises to have something for everyone. Whether you seek luxury, tranquillity, or family fun, there's a villa waiting for you.
Or speak to one of our Villa Specialists, available every day, who can provide personal recommendations and answer any of your questions, ensuring you find your perfect Tuscan villa. -
FAQs
1. What makes staying in a vineyard in Tuscany special?
A vineyard villa in Tuscany offers more than a beautiful setting; it allows guests to immerse themselves in the region’s wine culture. Many of our villas are located on working estates where guests can enjoy tastings, tours and strolls through the vines, making it the perfect way to combine relaxation with authentic Tuscan experiences.
2. Which areas of Tuscany are best for villas in vineyards?
The Chianti region between Florence and Siena is the most famous, thanks to its Chianti Classico wines and scenic rolling hills. However, villas in vineyards can also be found in Montalcino, known for Brunello, Montepulciano, home to Vino Nobile, and the Maremma, where prestigious Super Tuscan wines are produced. Each area offers a unique wine and landscape experience.
3. Can I do wine tastings if I stay in a villa in a vineyard?
Many villas in vineyards are part of working wine estates, which host tastings and tours. However, it will depend on the property if these experiences are provided at the villa and whether there is an additional cost.
4. Are vineyard villas in Tuscany suitable for families?
Absolutely. Villas in vineyards in Tuscany often feature spacious grounds, private swimming pools and self-catering facilities that make them ideal for family holidays. While adults can enjoy wine tastings and vineyard tours, children have plenty of space to run around and enjoy the open space.
5. When is the best time to stay in a vineyard villa in Tuscany?
Autumn is the best time to stay at a villa in a vineyard in Tuscany thanks to the harvest season, which offers the chance to experience the process of the wine harvest in practice and feel part of the vendemmia season. However, summer remains a favourite for warm weather and long, sun-filled days by the pool.
If you want to learn more about wine in Tuscany, from the different types produced across the region, wineries and estates to visit and festivals to attend then check our introductory guide to all things wine in Tuscany.
