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Holiday villas in Tuscany

Montalcino Area Holiday Villas, Tuscany

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Montalcino Area

Montalcino Area, Tuscany, Italy
22 br, 25 ba (22 Ensuite), Pool

Whether you’re gathering to celebrate, reunite, or plan for the future, Borgo Finocchieto offers ample space, luxurious amenities and a beautiful historic setting near Siena. Finocchieto was abandoned in the 1960s after nearly 800 years as a farming village, but it’s been restored to offer 22 bedrooms, event space for 50 and hotel-like comforts in what was once a manor house and farmhouses.

From
€850 - 16818 /nt

View Villa Borgo Finocchieto - Full property
Montalcino Area, Tuscany, Italy
6 br, 6 ba (6 Ensuite)

Villa Oddi, featuring 6 bedrooms, is one of the largest Villas of the estate. Its renovation has accentuated the beauty and charm of the residence with a personal touch of its owner, bringing it into the 21st century with state-of-the-art technology, home automation and a private screening theater with an 82 inches screen.

From
€5000 - 9790 /nt

View Villa Villa Oddi
Montalcino Area, Tuscany, Italy
5 br, 6.5 ba (5 Ensuite)

Enjoy the privacy of your own Tuscan home combined with resort-worthy amenities at Casa Biondi. Located on the Castiglion del Bosco estate in the Val d’Orcia region, the five-bedroom property has space for a large family or group of friends, rustic charm to spare and an ideal location just steps from the golf course.

From
€4000 - 9240 /nt

View Villa Villa Biondi
Montalcino Area, Tuscany, Italy
5 br, 6.5 ba (5 Ensuite)

Expand your horizons at Villa Sant’Anna. The panoramic views from this restored farmhouse encompass the best of Tuscany’s Val d’Orcia region, from rolling hills and vineyards to a golf course, and five bedrooms provide plenty of space for the whole family or large groups of friends.

From
€3800 - 8800 /nt

View Villa Villa Sant'Anna
Montalcino Area, Tuscany, Italy
5 br, 5.5 ba (4 Ensuite)

Set on the estate of Castiglion del Bosco in Tuscany’s Val d’Orcia region, Villa Stabbi pairs the charm of a traditional Tuscan country house with resort-worthy amenities and a stunning setting amid vineyards and a golf course. The property’s five bedrooms are divided between the main villa and a private guest house, perfect for larger families or groups of friends.

From
€3500 - 8470 /nt

View Villa Villa Stabbi
Montalcino Area, Tuscany, Italy
4 br, 5.5 ba (4 Ensuite)

If spending the night in a former police station doesn’t appeal at first, the warm, elegant Villa Chiusa will change your mind. Four bedrooms divided between a main house and guest house offer plenty of space and privacy, and the property’s infinity pool wows with panoramic views of the countryside around Montalcino.

From
€3200 - 8250 /nt

View Villa Villa Chiusa
Montalcino Area, Tuscany, Italy
9 br, 9.5 ba (9 Ensuite)

Once upon a time, Borgo Finocchieto was the center of a medieval Tuscan village. Today, the nine-bedroom manor house near Buonconvento is an up-to-date gathering place, its 14th-century foundations supporting an event space for fifty, teaching kitchen, media room, gym and Jacuzzi.

From
€6480 - 7840 /nt

View Villa Borgo Finocchieto
Montalcino Area, Tuscany, Italy
4 br, 5.5 ba (4 Ensuite)

With the stone exterior of a traditional Tuscan farmhouse and rustic-chic interiors, Villa Gauggiole is a dreamy four-bedroom retreat in the Val d’Orcia region. Spread out over a main villa and guest house, the property offers plenty of space and privacy, but thanks to its location on the Castiglion del Bosco estate, there are vineyards, trails and even a golf course just minutes away.

From
€3100 - 7260 /nt

View Villa Villa Gauggiole
Montalcino Area, Tuscany, Italy
3 br, 3.5 ba (3 Ensuite)

Once an olive-oil press for the estate of Castiglion del Bosco, Villa Oliviera has been converted to a charming three-bedroom escape for a family or a few couples. With stunning views of the area around Montalcino, breezy living spaces and quiet, private bedroom suites, the villa offers all the traditional architecture and views of the Tuscan countryside with touches of romance and luxury.

From
€2500 - 7260 /nt

View Villa Villa Oliviera
Montalcino Area, Tuscany, Italy
3 br, 3.5 ba (3 Ensuite)

Set on a hilltop next to the ruins of a medieval castle, Villa Castello offers a private, romantic retreat with panoramic views, intimate interiors and resort-worthy amenities. Three bedrooms make this restored farmhouse the perfect size for a family or a few couples, and its location on the Castiglion del Bosco estate in Tuscany’s Val d’Orcia region means there are plenty of outdoor activities nearby.

From
€2500 - 6875 /nt

View Villa Villa Castello
Montalcino Area, Tuscany, Italy
4 br, 4.5 ba (4 Ensuite)

Villa Casa del Fiume may have been a farmhouse once, but this restored four-bedroom Tuscan villa will make you feel like a noble. Set on the Castiglion del Bosco estate in the Val d’Orcia region, the property has commanding views of the area around Montalcino, a golf course and vineyards just steps away, jet set-worthy amenities like a private tennis court and a guest house with its own kitchenette.

From
€2500 - 6600 /nt

View Villa Villa Casa del Fiume
Montalcino Area, Tuscany, Italy
3 br, 3.5 ba (3 Ensuite)

Perched on a hilltop and surrounded by gardens, Villa Alba is a quiet retreat in the heart of Tuscany’s Val d’Orcia region. Located on the Castiglion del Bosco estate, the three-bedroom villa is the perfect size for a family vacation, offering a private, luxurious space, resort-worthy amenities and plenty of vineyards, fields and woods to roam.

From
€2500 - 6000 /nt

View Villa Villa Alba
Montalcino Area, Tuscany, Italy
7 br, 7 ba (6 Ensuite), Pool

Sitting on a spectacular estate of twenty-five acres and boasting stunning views of the hills, Villa Leopolda is a true gem of Tuscany’s beloved countryside. Villa Leopolda is situated in an unspoiled area south of Siena, between the fascinating wine region of Montalcino and the beautiful coast of Maremma.

From
€1551 - 2040 /nt

View Villa Leopolda
Montalcino Area, Tuscany, Italy
6 br, 6 ba (6 Ensuite)

Discover a lesser-known side of Tuscany at villa Pieve A Pava. Located in the Crete Senesi area just south of Siena, the six-bedroom property was once its own small borgo, but was recently converted to a luxury villa.

From
€1150 - 1690 /nt

View Villa Pieve A Pava
Montalcino Area, Tuscany, Italy
3 br, 3 ba (1 Ensuite)

If you’re an oenophile who dreams of a Tuscan vacation, villa Le Vigne is for you. Located on a working wine estate near Montalcino, the renovated 18th-century stone farmhouse is surrounded by vineyards, and guests can arrange to tour the on-site wine cellar and have a private tasting.

From
€736 - 915 /nt

View Villa Le Vigne