Villa La Castellana

7 Bedrooms - Sleeps 13
from $ 10,834
Per Week
The exterior of Villa La Castellana Tavarnelle Val di Pesa, Tuscany, Italy

Villa La Castellana proudly sits amongst 17,000 olive trees and centuries-old cypress trees with nothing but thriving vineyards and the gently rolling Tuscan countryside as far as the eye can see.

Villa San Casciano

6 Bedrooms - Sleeps 12
from $ 7,043
Per Week
Pool and patio with sun loungers, umbrellas, tables and view of countryside at Villa San Casciano in Tuscany, Italy Montespertoli, Tuscany, Italy

Villa San Casciano is perfectly positioned for those who want easy access to Florence whilst being surrounded by dreamy Chianti countryside.

Villa Il Sole

9 Bedrooms - Sleeps 20
from $ 13,852
Per Week
swimming pool of Villa Il Sole, Tuscany Tavarnelle, Tuscany, Italy

Located on the doorstep of the Chianti Classico region, Villa Il Sole is beautifully positioned to explore Florence and many of the best villages in Tuscany.

Podere Cipressi

6 Bedrooms - Sleeps 11
from $ 14,684
Per Week
Aerial of Podere Cipressi, Tuscany Tavarnelle Val di Pesa, Tuscany, Italy

Podere Cipressi is a converted Tuscan farmhouse which has been beautifully restored, with vaulted ceilings, arched doorways and generous outdoor space.

Villa Giuliana

6 Bedrooms - Sleeps 12
from $ 10,025
Per Week
Aerial view of the villa San Casciano in Val di Pesa, Tuscany, Italy

A pretty farmhouse set amidst lushly ordered vineyards and picturesque olive groves in the heart of the Chianti Classico region, very close to many of the best loved villages in Tuscany.

Villa Chiocchio

6 Bedrooms - Sleeps 11
from $ 8,891
Per Week
a view of the pool and the facade Greve-in-Chianti, Tuscany, Italy

Perfectly positioned for exploring the Chianti villages of Panzano & Greve, Chiocchio has a sensational pool, an Italian landscaped garden and tennis to play until the last rays of light.


7 Bedrooms - Sleeps 14
from $ 27,733
Per Week
The swimming pool, sun loungers and facade of Tramonti, Tuscany Castellina-in-Chianti, Tuscany, Italy

The sublime views, honey-hued stone walls and brilliant set up make this superbly designed property perfect for the contemporary Tuscan traveller.

Villa Baciata

5 Bedrooms - Sleeps 10
from $ 7,945
Per Week
Exterior of Villa Baciata in Tuscany Italy Castagnoli, Tuscany, Italy

Among the shimmering olive orchards and leafy vineyards, which line the hills of Chianti, is Villa Baciata, a wonderfully-restored Tuscan farmhouse with 40-acres of grounds, and origins dating back to the 18th century.

Villa delle Vigne

9 Bedrooms - Sleeps 18
from $ 35,229
Per Week
The pool at Villa Delle Vigne. Castellina-in-Chianti, Tuscany, Italy

Experience life on an authentic Tuscan wine estate in this remarkable villa, which provides a memorable venue for both a rural retreat and explorations of nearby Chianti, Siena and Florence.

La Regina

6 Bedrooms - Sleeps 12
from $ 38,445
Per Week
Pool and pool area with sun loungers, umbrellas, table tennis and countryside views at La Regina in Tuscany, Italy Panzano-in-Chianti, Tuscany, Italy

A contemporary six-bedroom villa in the heart of Chianti with breath-taking views from its commanding position and within walking distance to Panzano.

Villa Luce

9 Bedrooms - Sleeps 18
from $ 28,753
Per Week
View of Villa Luce in Tuscany Greve-in-Chianti, Tuscany, Italy

Perched above the bucolic hills of Chianti, Villa Luce is exceptional for larger families with spacious grounds and generous interiors. Particularly impressive is the beautifully designed kitchen which truly is the heart of this home.

La Tenuta

7 Bedrooms - Sleeps 14
from $ 31,479
Per Week
Exterior of La Tenuta in Tuscany Castellina-in-Chianti, Tuscany, Italy

Amidst the breath-taking hills of the Chianti region lies La Tenuta, a 13th-century estate which combines modern luxuries with traditional design.

Il Prato di Vignamaggio

9 Bedrooms - Sleeps 18
from $ 35,055
Per Week
Aerial view over Il Pratio di Vignamaggio and the surroundings near Chianti, Tuscany Greve-in-Chianti, Tuscany, Italy

Named after the owners' local wine estate, Il Prato di Vignamaggio is perfectly positioned between two of the region's great villages, Greve and Panzano-in-Chianti, each ten minutes away.

Villa Cispiano

10 Bedrooms - Sleeps 19
from $ 74,696
Per Week
Surroundings of Villa Cispiano in Tuscany Castellina-in-Chianti, Tuscany, Italy

A beautifully designed and recently renovated luxury villa in Tuscany. This hill-top retreat is located on an award-winning wine estate, surrounded with the rolling hills of Chianti.

Ca di Pesa

11 Bedrooms - Sleeps 22
from $ 34,615
Per Week
The swimming pool at Ca di Pesa. Panzano-in-Chianti, Tuscany, Italy

This traditional stone villa exudes Tuscan charm with magnificent views of the Chianti hills. The setting on a private vineyard estate is completely irresistible.

Villa Isabella

16 Bedrooms - Sleeps 32
from $ 68,898
Per Week
Aerial view of Villa Isabella and estate in Tuscany Colle di Val d'Elsa, Tuscany, Italy

A magnificent private Tuscan estate with expansive grounds and tennis court, in a prime location for exploring Siena, San Gimignano and the Chianti hills.

Villa Ardore

8 Bedrooms - Sleeps 16
from $ 54,330
Per Week
Aerial View of Villa Ardore in Provence Barberino Val d'Elsa, Tuscany, Italy

Perfectly located in the heart of Chianti, a delightful hill-top property set in a classically Tuscan landscape of cypress and vineyard.