5-Star Luxury Rentals Castellina in Chianti

Tucked into the rolling hills of Chianti, this villa sits on a working winery and olive oil farm – and yes, they do offer tastings. The lower half of the main villa is where the magic happens while up.....

Podere Gioia consists of two independent housing units. Our offer includes three apartments, two of which are in the same unit and the third apartment is a few meters away. Each apartment has an indep.....

Old farmhouse, renovated, with lovely view on the hills of Chianti Classico. Surrounded by vineyards. In the property there is the stone house which consists of 2 parts and the owner's farmhouse.Rusti.....

Old farmhouse, renovated, with lovely view on the hills of Chianti Classico. Surrounded by vineyards. In the property there is the stone house which consists of 2 parts and the owner's farmhouse.Rusti.....

Castellina in Chianti: Large, modern house "Terrazza sul Chianti", 2 storeys, renovated in 2025. 2 houses in the residence. 1.2 km from the centre of Castellina in Chianti, in a secluded, elevated pos.....

Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residence. 2.5 km from the centre of Castellina in Chianti, 11 km from the centre of Ra.....

Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residence. 2.5 km from the centre of Castellina in Chianti, 11 km from the centre of Ra.....

This Italian villa caught our eye for its panoramic views of the Tuscan countryside. There’s plenty to make your holiday memorable here, including both indoor and outdoor pools, a sauna, and a private.....

Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residence. 2.5 km from the centre of Castellina in Chianti, 11 km from the centre of Ra.....

You've got all the perks of a private home combined with the palatial shared grounds of a hamlet at this apartment complex nestled between the Chianti villages of Panzano and Castellina. The views of.....

Surrounded by olive trees and vast swathes of vineyards, this Tuscan home in the heart of the Chianti wine region is a haven of rural relaxation. Its exposed stone exterior gives way to a bright inter.....

From the countryside views to the traditional character inside, there's no denying that this home is unmistakably Tuscan. It's situated among a working vineyard, offering access to the estate's commun.....

With a truly picturesque location in the Chianti hills, this rustic villa is the ideal choice for anybody that has fantasised at any point about eloping to Tuscany for a short while — which is surely.....

Cosy and quaint, this typically Tuscan apartment is part of a pretty collection of homes, all set inside some historic stone buildings that feel charming and characterful. As such, you'll find terraco.....

Perched on a sun-kissed Chianti hillside, this home offers a quintessential Tuscan escape. Rustic stone walls and terracotta tiles give a traditional feel, while the private terrace is perfect for al.....

Casale il Poggino, located in a hilly position in the heart of the Chianti Classico, consists of two units, the farmhouse which is divided into three apartments (for 12 people) communicating with each.....

Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residence. 2.5 km from the centre of Castellina in Chianti, 11 km from the centre of Ra.....

This stone-built villa in the heart of Chianti boasts stunning views of the valley and vine-clad hillsides from almost every room. Perfect for two couples wanting to holiday together without crowding.....

Situated on the first floor of a traditional Tuscan stone building, this apartment puts you right at the heart of rural Tuscany, surrounded by glorious rosemary bushes, grape vineyards and olive grove.....

This apartment is a comfortable base from which to explore all that Tuscany has to offer. Siena, around 27 kilometres away, is an ideal day trip destination, while the small town of Castellina in Chia.....

If you’re in search of a rustic retreat in the heart of Chianti Classico, this home delivers a sweet solution. You can enjoy stunning views across olive groves, vineyards and rolling hills. There’s a.....

Pretty stone farmhouse. The property, made up of two connected units, is immersed in the countryside in the heart of Chianti, an ideal area for visiting Tuscany. Country house "Olimpia", 400 m a.s.l.,.....

Sitting on the hillside in Chianti's countryside, this apartment is part of a small collection of cottages and apartments. Typically Tuscan, the interior may be a tad dated – and you'll have to share.....

After a day touring world-class vineyards, this home is the perfect place to unwind with a glass of Chianti. Sure, there’s no air conditioning here, and the traditional interiors may not be to everyon.....

Old farmhouse, renovated, with lovely view on the hills of Chianti Classico. Surrounded by vineyards. In the property there is the stone house which consists of 2 parts and the owner's farmhouse.Rusti.....