Villas in Chianti for vacation rentals

We have evaluated and chosen for you and your family the best villas for vacation rental in Tuscany. Contact us and choose the villa that best suits your needs according to the area where you want to stay and the particular features of the villa you want to rent. In these pages you will find our proposals for villas in Chianti .


Chianti is certainly one of the most famous areas of Tuscany in the world. Made famous by the red wine Chianti DOCG, the area attracts tourists from around the world fascinated by the beauty of the landscapes and the peaceful atmosphere of its hills.

Chianti is the perfect place for a relaxing vacation, surrounded by breathtaking scenery and a few kilometers from major cities such as Florence, Siena, Arezzo and San Gimignano.

The farms, country houses and villas in Chianti are generally on hilltops and the path to reach them is characterized by lines of cypress trees. Around the houses, rows of vineyards and olive groves. Staying in one of our villas in Castellina in Chianti, Radda in Chianti or Gaiole in Chianti you will be right in the heart of the Chianti Classico on the Chiantigiana road. If you prefer to stay closer to Florence we recommend our villas in Greve in Chianti, San Casciano, Impruneta or Greve in Chianti. To all those who prefer quiet villages, the best choice is one of our villas in Dudda in Chianti, Panzano in Chianti or San Polo.

Well known as an international tourist destination, Chianti is not only famous for the beauty of its landscapes and its medieval villages, but also for its vineyards that, thanks to expert growers, produce some of the most popular wines in the world. This is a land to be discovered in every corner. A vacation looking for perfection not only for your eyes but also for the palate when the wine is accompanied to tasting of typical products such as extra-virgin olive oil, the `cinta senese`, the truffle, Tuscan salami and `pecorino` cheese.

This land is closely linked to agriculture and many folkloristic events and festivals in the country coincide with the most important moments of the agricultural year : in September, for example, there is the `Festa della Vendemmia` (Grape Harvest Festival) in Radda, the `Sagra della Bruschetta` (Bruschetta Festival) in Gaiole and the `Festa del Vino` (Wine Festival) in Greve in Chianti.

In this part of the site you will find our villas in Chianti with pictures and descriptions. Choose your favorite and do not hesitate to contact us.

Tuscany villa with pool near Radda in Chianti in the countryside of Chianti between Siena and Florence. Sleeps 12/13, Internet connection.
7 days: min: 1970 € - max: 2950 €
Country luxury villa in San Polo in Chianti near Florence. 10+2 sleeping accommodations, swimmming pool.
7 days: min: 1750 € - max: 3375 €
Tuscany villa for vacation rental in Panzano in Chianti, in the Chianti district, in the countryside around Florence. 10 sleeping accommodations, swimming pool, mountain bikes.
7 days: min: 1990 € - max: 2290 €
Villa with swimming pool in the Chianti region, in Tavarnelle Val di Pesa (Florence). Sleeps 4+2, Internet connection, air conditioning, children`s toys. Tennis courts and riding stable nearby.
7 days: min: 650 € - max: 1430 €
Elegant villa in Vico d`Elsa in the Valdelsa between Florence and Siena, near San Gimignano . Panoramic position, swimming pool and Jacuzzi hot tub in the garden, air conditioning, Internet WI-FI connection. 8 beds.
7 days: min: 1148 € - max: 2970 €
Castle in the heart of the Chianti district, near Florence. The castle is divided into apartments and includes a farmhouse with 4 to 12 sleeping accommodations. The complex accommodates up to 44 people. Swimming pool, park, breathtaking panorama.
7 days: min: 556 € - max: 8290 €
Villa in San Polo in Chianti, near Florence. 6 sleeping accommodations, panoramic terrace and swimming pool.
7 days: min: 980 € - max: 1850 €
Holiday Tuscany villa for rent in the heart of the Chianti district, between Greve in Chianti and Panzano in Chianti. Sleeps 4+1, swimming pool, air conditioning system.
7 days: min: 900 € - max: 1380 €
Farmhouse near San Polo in Chianti (Florence). The farmhouse is located on the top of a hill and offers a breathtaking view on the Arno river valley and on Vallombrosa mountains. Swimming pool, 10/14 beds.
7 days: min: 1690 € - max: 2590 €
Historical medieval castle in the heart of the Chianti district, near Florence. The castle accommodates up to 25 people in 8 bedrooms from 2 to 4 sleeping accommodations. Swimming pool.
7 days: min: 9335 € - max: 9335 €
Holiday farmhouse in the heart of the Chianti Classico district, near Siena. 4/6 sleeping accommodations, garden, swimming pool, Internet connection.
7 days: min: 1130 € - max: 1630 €
Villa for vacation rentals in Siena countryside. 4+2 sleeping accommodations, swimming pool.
7 days: min: 1016 € - max: 1544 €
Exclusive luxury villa with swimming pool near San Gimignano, in Valdelsa, between Florence and Siena. 10 sleeping accommodations, satellite TV, air conditioning, barbecue, Internet connection.
7 days: min: 4000 € - max: 5650 €
Luxury villa wit swimming pool near Impruneta, on the hills surrounding Florence. 12/24 sleeping accommodations, billiard table, table-tennis table, Internet connection, air conditioning in the bedrooms of the main villa.
7 days: min: 890 € - max: 10833 €
Elegant luxury villa in Barberino Val d`Elsa (Florence), in the Chianti Classico region. Sleeps 10, swimming pool, air conditioning, Internet connection. Riding stable in the neighbourhood.
7 days: min: 2670 € - max: 5300 €
Ancient castle in the Chianti district, near Florence. Sleeps 15/20, swimming pool, Internet connection, table-tennis table. Riding stable, tennis courts and golf club nearby.
7 days: min: 7080 € - max: 9085 €
Holiday villa for rent a few kilometres from San Gimignano, in Valdesa counryside, between Florence and Siena. 8 sleeping accommodations, swimming pool, Internet connection. Air conditioning in the bedrooms of the villa.
7 days: min: 1733 € - max: 3335 €
Luxury villa with breathtaking view over Siena. 10+2 sleeping accommodations, swimming pool, satellite TV.
7 days: min: 3190 € - max: 3990 €
Farmhouse in the Chianti region, near Siena. 8+2 sleeping accommodations, swimming pool, Internet connection. Panoramic position with views of Siena, the hills of Chianti and the Crete Senesi region.
7 days: min: 1625 € - max: 2625 €
Farmhouse in Tuscany between the Casentino and the Chianti, in Castelfranco di Sopra, in the province of Arezzo. 8/9 sleeping accommodations, swimming pool, barbecue, wonderful panorama.
7 days: min: 1070 € - max: 2150 €
Holiday houses with swimming pool in Dudda in Chianti, in the Chianti district, near Florence. Every house accommodates 7+2 people. 9/18/27/36 beds.
7 days: min: 1446 € - max: 10022 €
Prestigious and exclusive villa with swimming pool in a historical castle in Pelago, on the hills surrounding Florence, in Valdisieve. 12+2 sleeping accommodations, hydromassage, wonderful panorama, billiard table.
7 days: min: 3875 € - max: 6250 €
Farmhouse in Tavarnelle in Val di Pesa, in the Chianti region, between Florence and Siena. Sleeps 8/11, garden, swimming pool, hydromassage, Internet connection, barbecue. Riding stables and tennis courts nearby.
7 days: min: 1700 € - max: 3780 €
Apartment in farmhouse for rent in Tavarnelle Val di Pesa (Florence), in Florentine Chianti . Sleeps 6+1, swimming pool, air conditioning, Internet connection. Tennis courts, golf club and riding stables in the neighbourhood.
7 days: min: 1620 € - max: 2835 €
Holiday villa in Montespertoli, in Florentine Chianti, between Florence and Siena. 8/11 sleeping accommodations, fully enclosed garden, hydromassage. Trekking routes in the surroundings.
7 days: min: 1590 € - max: 2585 €
Two villas immersed in the green Chianti countryside, about 400 metres from the famous square of Greve in Chianti (Florence). 6/10/16 sleeping accommodations. Two swimming pools.
7 days: min: 1080 € - max: 5065 €
Elegant luxury villa in Certaldo (Florence), in Empoli countryside. Sleeps 13, wide garden, swimming pool, Internet connection, and barbecue. Tennis club and riding stable within a few kilometres.
7 days: min: 2879 € - max: 4469 €
Portion of a farmhouse in Montespertoli ( Florence ), in Empoli countryside, at the border with Chianti. Sleeps 6, swimming pool, Internet connection, air conditioning, hydromassage, toys for children. Tennis courts, riding stable and golf club nearby.
7 days: min: 1595 € - max: 2025 €
Elegant historic luxury villa dating from the 17th century near Impruneta , a small picturesque town in the Chianti countryside, near Florence . Sleeps 12/16, wide garden, swimming pool, Internet connection, air conditioning, gym, Tennis courts, riding stable and golf club nearby.
7 days: min: 3780 € - max: 7560 €
Elegant villa (in the past an aristocratic residence) in Valdelsa, in Monteriggioni (Siena). Sleeps 11, park, swimming pool, air conditioning, Internet connection, panoramic terrace.
7 days: min: 4200 € - max: 5600 €
Ancient church transformed into an elegant villa with 6 sleeping accommodations. The villa is situated in Valdelsa, close to San Gimignano (Siena). Swimming pool.
7 days: min: 1000 € - max: 2500 €
Villa in Chianti, near Monteriggioni (Siena). The villa is divided into three apartments and sleeps 11+3. Swimming pool, Internet connection, air conditioning. Tennis courts, riding stable and golf club within a few kilometres.
7 days: min: 1440 € - max: 5200 €
Luxury villa dating from the early 20th century on the hills around Montespertoli (Florence). The villa is situated in Empoli countryside, in Lower Valdarno, just a few kilometres from the Florentine Chianti region. Sleeps 8, swimming pool with whirlpool corner, Internet connection, air conditioning and barbecue. Tennis club and golf club nearby.
7 days: min: 3160 € - max: 4740 €
Ancient farmhouse in Greve in Chianti (Florence) with view over the surrounding countryside and nearby Florence. Sleeps 12, wide garden, swimming pool, Internet connection, and barbecue.
7 days: min: 1530 € - max: 2811 €
Villa in the Chianti region, in Montespertoli, at a close distance to Florence historic centre. Sleeps 8+1, wide garden, swimming pool, barbecue.
7 days: min: 920 € - max: 1441 €
Ancient tower of a historic 11th-century castle near Siena, in the Chianti district. Sleeps 5+2, garden, swimming pool, Internet connection, air conditioning. Tennis courts and riding stable nearby.
7 days: min: 1200 € - max: 2000 €
Villa with private swimming pool in the region of Montagnola Senese, near Sovicille (Siena), in a peaceful and panoramic position. Sleeps 8, air conditioning, wide garden, barbecue equipment. Just a few kilometres from Siena and the towns of the Chianti district.
7 days: min: 1800 € - max: 3000 €