Holiday villas for rent in Chianti


Whether you come to Tuscany for the first time or you know it well, a holiday villa in Chianti is definitely the ideal choice for all lovers of good wine, hilly landscapes of infinite beauty and the tranquility of an area still rich of events and a wide range of outdoor activities. We are an agency specialized in holiday rentals and here we offer you the best offers for holiday villas in Chianti.


Defining the boundaries of Chianti is not simple. The area is so popular in the world that almost every town would like to be part of it. A first differentiation is thanks to the production of wine: Chianti Classico can only be produced in the area between Florence and Siena while the Chianti wine is produced in many provinces of Tuscany with different labels. Hence, for example, Chianti Colli Aretini and Chianti Colli Pisani. The Chianti Classico area, however, remains the most famous and well known area for its history, its medieval villages that have created the legend of the Chianti region since 1300 and its scenery.

If you want to stay in the heart of the Chianti Classico we suggest you rent one of our villas in Castellina in Chianti with its imposing medieval tower and the charming street covered by vaults of the sixteenth century or one of our villas in Radda in Chianti to discover an area rich in castles and vineyards. Among the villas in San Casciano in Val di Pesa or Tavarnelle Val di Pesa you might find the ideal one for you, near Florence and nestled in the hills of Chianti. By choosing one of the villas in Greve in Chiantiyou'll stay in one of the historical towns of Chianti and you will be just a few kilometers from Florence.


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Villa Botticelli Villa Botticelli

Villa for vacation rental in Radda in Chianti, between Florence and Siena, in the Tuscan countryside. Accommodation for 10 people, garden, swimming pool, panoramic view, Internet connection.

7 days: min: 1750 € - max: 2800 €
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Villa Siena Villa Siena

Villa with swimming pool for rent near Siena for holidays in Tuscany. Villa with accommodation for 4/6 people, panoramic view on Siena.

7 days: min: 1016 € - max: 1544 €
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Farmhouse Flora Farmhouse Flora

Farmhouse between Siena, Arezzo and Florence and close to the Chianti Classico region. Sleeps 8+2, garden, olive grove, wide swimming pool, wireless Internet connection, bathroom with Jacuzzi bathtub, fireplace.

7 days: min: 1230 € - max: 2460 €
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Castle Torre Chianti Castle Torre Chianti

Apartment sleeping 5+2 in the tower of an 11th-century castle in Sienese Chianti, near Gaiole in Chianti. Swimming pool, air conditioning, Internet connection, utmost privacy. Riding stable and tennis club in the neighbourhoods.

7 days: min: 1277 € - max: 2128 €
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Villa Letizia Villa Letizia

Luxury villa with private swimming pool in Siena, in Tuscany. Elegant villa with accommodation for 10+2 people.

7 days: min: 3190 € - max: 4665 €
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Farmhouse Castelfranco Farmhouse Castelfranco

Ancient farmhouse with swimming pool at the border between the Chianti and the Casentino, in Castelfranco di Sopra (Arezzo). 8/9 sleeping accommodations, wonderful panorama, barbecue.

7 days: min: 1070 € - max: 2010 €
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Villa Gallo Villa Gallo

Villa sleeping 6 in the Chianti Classico area, a few kilometres from Castellina in Chianti (Siena). Air conditioning, swimming pool, Internet connection. Possibility of organising dinners and wine tasting events to the property.

7 days: min: 750 € - max: 1700 €
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Villa Zanobi Villa Zanobi

Cosy country house sleeping 8 in Sienese Chianti, a few kilometres from Gaiole in Chianti. Garden, wood-burning oven, swimming pool, children's playground with swing set and slide, Internet connection, air conditioning.

7 days: min: 1530 € - max: 2555 €
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Villa Amerigo Villa Amerigo

Country house sleeping 16 a few kilometres from Siena, in the Chianti Classico area. Wide garden, swimming pool, Internet connection, air conditioning. Possibility of purchasing the produce of the farm and of tasting wines.

7 days: min: 1990 € - max: 5465 €
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Villa Marie Villa Marie

Elegant 18th villa sleeping 11+3 divided into three apartments in Monteriggioni (Siena), in Chianti, close to Valdelsa. Wide garden, swimming pool, Internet connection, air conditioning. Riding stable, tennis courts and golf club nearby.

7 days: min: 2900 € - max: 5600 €
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Villa Panorama Villa Panorama

Villa sleeping 8 in Valdelsa, near Sovicille (Siena). Wide garden, swimming pool, barbecue, air conditioning. Wonderful view over the surrounding countryside and the town of Siena. A few kilometres from the Chianti region.

7 days: min: 1845 € - max: 3075 €
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Villa Cattaneo Villa Cattaneo

Villa sleeping 12 for rent between Florence and Siena, in the Chianti Classico region, near Castellina in Chianti. Swimming pool, Internet connection, air conditioning, barbecue. Possibility of purchasing the produce of the farm. Gorgeous panorama.

7 days: min: 2725 € - max: 5115 €
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Villa Stefania Villa Stefania

Small villa sleeping 6 a few kilometres from San Gimignano (Siena), in the Chianti region. Internet connection, swimming pool.

7 days: min: 1240 € - max: 2280 €
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Villa Santa Lucia Villa Santa Lucia

Luxury villa for rent in Staggia Senese, near Monteriggioni (Siena), in Valdelsa. Sleeps 14, swimming pool, wide garden, Internet connection, air conditioning.

7 days: min: 3640 € - max: 6440 €
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Villa Navigatore Villa Navigatore

Beautiful villa sleeping 8 near Gaiole in Chianti (Siena), in the Chianti Classico region. Heatable swimming pool, air conditioning, Internet connection, Finnish sauna. Possibility of organising well-being itineraries, cooking lessons and wine tasting events. Breathtaking panorama, utmost peace and privacy.

7 days: min: 3240 € - max: 4860 €
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Farmhouse Gina Farmhouse Gina

Farmhouse in the Chianti Classico region, in Castelnuovo Berardenga, in the province of Siena. 4/6 sleeping accommodations, swimming pool, garden, Internet connection.

7 days: min: 1240 € - max: 1735 €
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Farmhouse Siena Farmhouse Siena

Holiday farmhouse sleeping 9 near Siena, in the Chianti region. Swimming pool, hydromassage, Internet connection. Wonderful view of the Crete Senesi and Chianti regions and of Siena.

7 days: min: 1625 € - max: 2625 €
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Farmhouse Pestello Farmhouse Pestello

Farmhouse sleeping 12 near Montevarchi (Arezzo), in Upper Valdarno. Garden, swimming pool, basketball/tennis/volleyball pitch, Internet connection, hydromassage, air conditioning. Beautiful view of the valley of the Arno and the ridge of Pratomagno. Possibility of organising wine tasting events and cooking lessons.

7 days: min: 2385 € - max: 4405 €
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