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A beautiful villa set on an award-winning wine estate, surrounded by rolling Tuscan hills

Set in the Tuscan countryside, just outside the Renaissance town of Montepulciano, Villa Chiani is a true beauty. With views over its own vineyards along with the stunning Val di Chiana, this romantic hideaway offers guests an authentic Tuscan experience.

Located on a wine estate of over 50 hectares, this five-bedroom villa is surrounded by vineyards, olive groves, fruit orchards, truffle hunting grounds, and lush forests. The on-site Icario Winery produces some of the region’s most revered wines, including Vino Nobile di Montepulciano, and guests can take tours and enjoy wine tastings or lunches during their stay.

The private grounds of the villa include verdant lawns and gardens blossoming with fragrant roses and jasmine, along with a host of native plants, creating a relaxing ambience. A vast infinity pool overlooks the undulating valleys and is lined with sun loungers, perfect for soaking up the sun after a swim.

These views can also be enjoyed from the various outdoor lounge and dining areas, which are spread across the grounds and the villa’s many terraces and patios. In the barbecue area, guests can enjoy the traditional wood-fired fireplace for a rustic experience or the modern gas grill for quick, convenient al fresco meals.

The estate comprises three buildings, which include a restored rural mansion and two guest cottages. The main villa features a comfortable living room with plush sofas and a large country kitchen with an expansive wooden dining table, perfect for entertaining. The three spacious bedroom suites each feature king-size beds and en-suite bathrooms.

The quaint Sansasio Cottage has an open-plan, studio setup. The main space features a king-size bed, a living area with a sofa bed, and a kitchenette. It also boasts an en-suite bathroom and a private patio, perfect for enjoying the views in tranquillity.

The Monterosso Cottage is set across two floors. The ground floor features a king-size bed and doors leading directly out to the garden and pool area. The lower level is home to a lounge area with a wine bar and a dedicated yoga & fitness space, as well as a spacious bathroom with a Jacuzzi.

The beautiful surroundings, on-site winery, and vast swimming pool make Villa Chiani the perfect choice for families and friends seeking a relaxing escape in the Tuscan countryside.

Highlights

Swimming Pool

Swimming Pool

Jacuzzi

Jacuzzi

Countryside Views

Countryside Views

Services

Included

Available extras

Enhance Your Stay with Personalised Services

After booking, your dedicated concierge will craft the perfect experience — tailored to your preferences. From everyday essentials to exclusive experiences, our curated add-ons elevate every villa stay.

Essential

Essential

Signature

Signature

Prestige

Prestige

Features

Indoor

Outdoor

Bedrooms

This property comfortably accommodates up to 10 guests in its 5 bedrooms.

MAIN VILLA – SECOND FLOOR
Nysa Junior Suite – king-size bed and en-suite bathroom with shower
Vitaroccia Junior Suite – king-size bed and en-suite bathroom with shower
Nobile Suite – king-size bed, private living room with sofa bed, and en-suite bathroom with bathtub/shower

SANSASIA COTTAGE
Sansasio Suite – king-size bed, living area with sofa bed & kitchenette, en-suite bathroom with shower, and private patio

MONTEROSSO COTTAGE
Monterosso Suite – king-size bed, lounge area with bar & yoga/gym space, en-suite bathroom with Jacuzzi bathtub, and garden access

Nb. Up to 4 children or 2 adults may be accommodated on sofa beds on request.

Location

Disclaimer: the location on the map may be approximate due to privacy reasons.

About the area

Villa Chiani is ideally located on the outskirts of Montepulciano, a Renaissance gem in the province of Siena. Famed for its deep artistic roots and a winemaking heritage dating back to the Etruscans, the town remains a premier destination for history and culture enthusiasts.

The region offers a rich array of experiences, from vineyard tours and wine tastings to traditional cooking classes and museum visits. For those seeking adventure, the rolling Tuscan landscape is best explored via guided bike tours or breathtaking hot air balloon flights over the Val d’Orcia.

The villa provides easy access to Tuscany’s most iconic sites. Guests can quickly reach the UNESCO-listed city of Pienza, the Gothic splendour of Siena, and the historic streets of Arezzo and Cortona, making it a perfect base for discovering the cultural heart of Italy.

Distances

Frequently asked questions

Inclusions vary by property but generally cover accommodation, cleaning services, and basic utilities. Some villas may also include additional services such as concierge, breakfast, or a private chef. Full details can be found on each villa’s page. If a service is not included in the price, our concierge team can arrange it for you, ensuring a fully personalised stay. Let us know your preferences, and we’ll take care of the rest!
Booking is simple! If you have a specific villa in mind, click "Send Enquiry" on its page. If you're considering multiple options, click the heart icon to save your favorites and send one enquiry for all of them. Our team will check availability and send you a detailed offer within 24 hours. Need help choosing? We’re happy to assist!
Yes, a deposit is required at the time of booking, typically 30% of the total amount. The remaining balance is usually due 30 to 90 days before check-in, depending on the property. Some villas may have different payment schedules, which will be specified in the offer we send you.
We accept bank transfers and major credit cards. Payment details will be provided during the booking process.
Yes, we offer a wide range of services, including in-villa options like private chefs, chauffeurs, and spa treatments, as well as activities such as yacht charters, wine tastings, and guided tours. We can also arrange experiences for the rest of your holiday, even beyond your villa stay. After booking, your dedicated concierge will contact you to customise your itinerary.
Yes, most high-end villas require a minimum stay of 7 nights, usually starting from a Saturday. However, many properties offer flexibility during certain times of the year, except for peak seasons like summer and Christmas holidays, which typically have stricter requirements. A smaller number of properties accept shorter stays year-round. If you have specific dates in mind, please contact us for availability.

Have more questions?

Connect with our Villa Experts – we’ll handle the rest.

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From EUR 14,000 to EUR 18,000 per week

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"Just ended the most epic week celebrating my parents 50th anniversary in this gorgeous villa which has amazing facilities like a separate gym, a huge terrace with surreal views of the mountains and Bellagio, a gorgeous pool, and a ping pong table. This kept the kids happy which means it let us adults rest. The villa was kept super clean with the most helpful Terrence who made everyone of us feel at home. Terrence kept the kitchen stocked, and helped organised everything. Mauro, Michael and Elisabetta's breakfasts and dinners were fantastic and we really got to experience Italian hospitality. Chef Mauro's cooking class and Angela's yoga class were a family trip highlight. Thank you to all for making this such a memorable holiday "

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