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, green rolling hills, this area of Tuscany never ceases to amaze its visitors.




Results: 22 villas found
Pages:  123

Tuscany, monteroni d'arbia
Price On demand
 12    6    9

The setting of the top luxury villa for rent in Italy La Tenuta is undoubtedly the same as the imaginary sceneries of all those who dream of the enchanting Tuscan countryside. A stone dwelling situated on a hilltop of medium height which dominates one of the most beautiful valleys of the ...

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Tuscany, cetona
from 6,800 to 12,600 € / week
 10    5    4

In southern Tuscany, not far from Montepulciano, this corner of paradise is located at a four-kilometre distance from Piazze and seven kilometres from Cetona. The villa offers a panoramic view of 360 ° from the Val di Chiana to the Cetona mountain. The highlight of this haven of peace is the ...

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Tuscany, rapale
from 7,100 to 11,900 € / week
 18    9    9

If you’re looking for Tuscan rolling hills, sloping vineyards, olive groves, quaint medieval villages, and outstanding art, you’ll find it all here at Villa Merlini. This exclusive large family villa for rent featuring 9 bedrooms is located in the heart of the charming Tuscan ...

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Tuscany, Castellina in Chianti
from 13,800 to 26,900 € / week
 14    7    8

In the heart of the Chianti area, at just 25 minutes from Siena and 50 minutes from Florence, villa Olivia is a luxury retreat offering the best of everything you could wish for a holiday rental in Tuscany. Dating back to the 17th century, the villa is set in a large estate beyond a narrow road ...

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Tuscany, Casole d'Elsa
Price On demand
 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
Price On demand
 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, casole d'elsa
from 8,200 to 16,900 € / week
 12/14    6    5

This traditional six-bedroom luxury villa, called Porcilia, is the quintessence of the typical Tuscan country house; traditionally built in stone, its ancient structure has remained intact during the centuries. The mixture of deluxe and rustic makes this Italian family villa for rent a charming ...

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Tuscany, radda in chianti
from 11,450 to 17,950 € / 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 12,600 to 20,600 € / 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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Results: 22 villas found
Pages:  123