Siena - Chianti area

top-class wine, historic towns, green rolling hills, treat yourself to an unforgettable luxury villa experience


Rent one of Home in Italy's high-end villas in the Chianti or Siena area and treat yourself to an authentic Italian holiday experience. Thanks to its lush landscape and delectable food and wine, a vacation in this well-renowned area of Tuscany is always a sensory overload in the best way. With its top-class wine, historic and charming villages, and green rolling hills, this area of Tuscany never ceases to amaze its visitors.




Results: 25 villas found
Pages:  12

Tuscany, Gaiole In Chianti
from 13,500 to 16,900 € / week
 8/10    4    5

Located in the picturesque wooded area of Chianti, just thirteen kilometers from Gaiole in Chianti, this luxury Italian villa for rent is the perfect destination for those who want to enjoy a tranquil holiday in Italy surrounded only by nature, far from the town and city life. Spread over two ...

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Tuscany, Casole D'Elsa
from 18,900 to 28,000 € / week
 8    4    5

If you want to rent a luxury holiday villa in Tuscany near places to discover, medieval villages, churches, and other spots of cultural interest and use the villa as an exclusive retreat to relax in between activities, Pietti is the place to be. Pietti is set in the iconic Tuscan countryside, ...

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Tuscany, Colle Di Val D'Elsa
from 18,900 to 28,000 € / week
 8    4    5

If you want to rent a luxury holiday villa in Tuscany near charming cultural places to discover, churches, medieval villages, and use the retreat as a lovely spot to enjoy relaxation in between activities, Poggio Corona is the place to be. This exclusive Italian home is set in the iconic ...

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Tuscany, Radda In Chianti
from 13,350 to 20,000 € / week
 10    5    9

Conveniently located midway between Siena and Florence, in the Tuscany region, this luxury holiday villa for rent lies just outside the charming medieval town of Radda in Chianti. Lovingly restored into a luxury modern Italian home, Pratomaggio features various facilities ensuring utmost comfort ...

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Tuscany, Castellina In Chianti
from 12,750 to 23,000 € / week
 18/22    9    8

This large Italian holiday villa for rent is set in one of the most beautiful areas of Tuscany, the Chianti region, at about ten minutes driving to the lovely town of Castellina in Chianti. Beautifully restored in 2021, this high end vacation home comprises the main villa and two guest houses, ...

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Tuscany, Castelnuovo Berardenga
15,750 € / week
 10    5    7

Privacy is the premium at villa Tea. A vacation in this holiday home for rent in Tuscany, surrounded by rolling hills, sloping vineyards and olive groves, is a perfect retreat for just you, your friends and family to get away from it all. Behind the simplicity of a typical Tuscan farmhouse, ...

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Tuscany, Panzano In Chianti
from 28,000 to 49,500 € / week
 34/37    17    19

It is worth renting a large luxury villa for your Tuscan holiday when you need rest and relaxation together with your family or friends. Within a splendid eight hectares (twenty acres) estate in the heart of Chianti, three splendid villas have recently been renovated and furnished for holiday ...

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Tuscany, Colle Val D’elsa, Siena
Price On demand
 26 • 32    16    16

Situated in the heart of Tuscany between Siena and Florence, Villa Contessa is a large top luxury retreat for vacation rentals, ideal for the celebration of important events such as weddings. This grand home owned for centuries by an Italian aristocratic family is encircled by spectacular gardens ...

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Tuscany, Colle Val D’elsa, Siena
Price On demand
 26 • 32    16    16

Situated in one of the most charming areas of Tuscany, between Siena and Florence, Villa Contessa is the ideal top luxury venue to rent to celebrate your wedding day in Italy. This splendid large villa offers breathtaking views of the typical Tuscan countryside and is surrounded by carefully ...

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Tuscany, Gaiole In Chianti
from 13,200 to 26,950 € / week
 10 • 14    7    8

Nestled in the heart of Chianti, Tuscany, this meticulously renewed 400-year-old luxury villa for rent in Italy is a dream destination for an exclusive Italian vacation. The careful restoration has retained the luxury holiday home's original character while infusing it with modern amenities, ...

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Results: 25 villas found
Pages:  12