Castellina in Chianti Castellina in Chianti is a city located on top of a beautiful green hill, seperating the Pesa and Staggia river. This small town is situated at the road that connects Florence to Siena, called the Via Chiantigiana. Castellina in Chianti is a historic town, with origins going back to Etruscan times. It was an important outpost because of its position between Florence and Siena. During times of battles, the city was destroyed and rebuilt many times, increasing the defensive walls every time the town was reconstructed. The Via della Volte is a covered street or tunnel, situated along the ancient walls, once used by guards, now used for shops and restaurants. You’ll be able to find more shops at the main street of Castellina in Chianti, called the Via Ferruccio, but also beautiful places such as Palazzo Banciardi and Palazzo Squarcialupi. These palaces both belong to local important families and the Palazzo Squarcialupi already serves as a wine shop for over 100 years, where you of course will find the delicious Chianti Classico wine. Just outside the city centre, the Fortress with its tall tower can be found, which offers a great view over the town and countryside. Another place that must be visited as well is the Church of San Salvatore, dating back to the 16th century, built in neo-Romanesque style. It contains important frescos, statues and a crucifix. If you like archaeology, the Archaeological Museum of Chianti is definitely something for you, where an Etruscan tomb buried under a tumulus on Monte Calvario and Etruscan necropolis of Poggino can be found. Castellina in Chianti is located at approximately 55 km from Florence, so the easiest option is to fly to Florence and take the car from there. Another option is to fly to Pisa, which is around 100 km from Castellina in Chianti and take the car from there as well.

The most known and visited area of Tuscany is the Chianti area, comprising around eight Chianti towns. The borders of this area aren’t very clear, but it can be said that in general it extends over the provinces of Florence and Siena, covering all of the area between the two cities and extending to the east toward the Valdarno and to the west to the Val d'Elsa. The Chianti landscape is unique and very beautiful, including picturesque little village, forests and hills covered with vineyards and olive trees. This region is of course also famous for its outstanding red wines, presented in bottles in woven baskets. The Chianti wines are characterized by intense aromas of fruit and flowers, easily drinkable with a smooth aftertaste. Traditional farming is still an everyday part of life in this region, including as afore mentioned wine making, but also olive oil production is very important here, making this region so attractive to tourists. 

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There are 155 villas still available of the total of 5 villas

Annalisa (6 persons) - Italy, Tuscany, Gambassi Terme

Villa popularity 2024: 98% booked

Annalisa has been made in an old stone haybarn which, thanks to a careful renovation, has been transformed into a comfortable country house. The house lies within a large estate of 62 hectacres near Gambassi Terme in the florentine chianti hill... read more »

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Citycenter
Lowest week price
6
private pool
45 km
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Serena (10 persons) - Italy, Tuscany, Talamone

Villa popularity 2024: 65% booked

Talamone is a delightful coastal village lying on a small promontory overlooking the gulf at Argentario and behind is the Maremma Nature Park. These days it has become a well known resort with a well equipped port for tourism, and the bay is ideal f... read more »

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Pool
Citycenter
Lowest week price
10
private pool
25 km
€ 6.671,-

Pierluigi (12 persons) - Italy, Tuscany, Poggibonsi

Villa popularity 2024: 98% booked

Fine villa situated in the hills of the Chianti Classico area just a short distance from Poggibonsi, just 3 kms away, where guests can find shops of all kinds. All the most famous place in Chianti are within easy reach of the villa, such as Castelli... read more »

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Pool
Citycenter
Lowest week price
12
private pool
40 km
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Alessandra (12 persons) - Italy, Tuscany, Castellina in Chianti

Villa popularity 2024: 100% booked

Villa Alessandra is a large and attractive stone farmhouse, lying within the old Lilliano estate, in a panoramic position surrounded by the estate vineyards and olive groves and with a splendid view of the Chianti hills. The recent renovation h... read more »

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Citycenter
Lowest week price
12
private pool
20 km
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Lisa (10 persons) - Italy, Tuscany, Castellina in Chianti

Villa popularity 2024: 100% booked

Villa Lisa is a classic stone farmhouse going back to 1500. It started out as a chapel and in 1876 underwent its first transformation into a farmhouse. Today, thanks to a careful renovation, the house has been transformed into a lovely country resid... read more »

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Pool
Citycenter
Lowest week price
10
private pool
20 km
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Saverio (15 persons) - Italy, Tuscany, Montepulciano

Villa popularity 2024: 100% booked

Saverio is made up of two ancient, stone-built country houses, situated one next to the other, only 900 m from the old city centre of Montepulciano. This splendid town is also called "The Pearl of the 1500s", protected by its ancient Renaiss... read more »

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Pool
Citycenter
Lowest week price
15
private pool
65 km
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Giulia 32 (32 persons) - Italy, Tuscany, Colle di Val d'Elsa

Villa popularity 2024: 98% booked

This splendid residence, which dates back to 1400, is located in the heart of the Tuscan countryside, between Florence and Siena and is an ideal place for those who love peace and quiet, being surrounded by nature, and living the atmosphere of the t... read more »

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Citycenter
Lowest week price
32
private pool
30 km
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Giulia 26 (26 persons) - Italy, Tuscany, Colle di Val d'Elsa

Villa popularity 2024: 98% booked

This splendid residence, which dates back to 1400, is located in the heart of the Tuscan countryside, between Florence and Siena and is an ideal place for those who love peace and quiet, being surrounded by nature, and living the atmosphere of the t... read more »

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Pool
Citycenter
Lowest week price
26
private pool
30 km
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Mila 14 (14 persons) - Italy, Tuscany, Barberino Val d'Elsa

Villa popularity 2024: 98% booked

Characteristic rural complex that has been recently built with great care, perfectly furnished and equipped. The complex consists of a large farmhouse and a hayloft, situated in a nice, panoramic position, set amidst the gently rolling hills of the ... read more »

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Citycenter
Lowest week price
14
private pool
35 km
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Mila 8 (8 persons) - Italy, Tuscany, Barberino Val d'Elsa

Villa popularity 2024: 98% booked

Characteristic rural complex that has been recently built with great care, perfectly furnished and equipped. The complex consists of a large farmhouse and a hayloft, situated in a nice, panoramic position, set amidst the gently rolling hills of the ... read more »

Persons
Pool
Citycenter
Lowest week price
8
private pool
35 km
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Mila 6 (6 persons) - Italy, Tuscany, Barberino Val d'Elsa

Villa popularity 2024: 98% booked

Characteristic rural complex that has been recently built with great care, perfectly furnished and equipped. The complex consists of a large farmhouse and a hayloft, situated in a nice, panoramic position, set amidst the gently rolling hills of the ... read more »

Persons
Pool
Citycenter
Lowest week price
6
private pool
35 km
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Rebecca (11 persons) - Italy, Tuscany, Castellina in Chianti

Villa popularity 2024: 87% booked

Large stone-built farmhouse located inside a vast property that extends for 460 hectares, situated in a peaceful and panoramic position overlooking the vineyards and the gentle hills of the Chianti Classico (350 m altitude) and near the farm centre.... read more »

Persons
Pool
Citycenter
Lowest week price
11
private pool
20 km
€ 1.680,-

Letizia (7 persons) - Italy, Tuscany, Castellina in Chianti

Villa popularity 2024: 90% booked

This characteristic, stone-built farmhouse is located inside a vast property that extends for 460 hectares, situated in a peaceful and panoramic position overlooking the vineyards and the gentle hills of the Chianti Classico (350 m altitude). Inside... read more »

Persons
Pool
Citycenter
Lowest week price
7
private pool
20 km
€ 1.085,-

Miriam (8 persons) - Italy, Tuscany, Castellina in Chianti

Villa popularity 2024: 92% booked

This characteristic, stone-built farmhouse is located inside a vast property that extends for 460 hectares, situated in a peaceful and panoramic position overlooking the vineyards and the gentle hills of the Chianti Classico (350 m altitude). Inside... read more »

Persons
Pool
Citycenter
Lowest week price
8
private pool
20 km
€ 1.232,-

Giorgia 16 (16 persons) - Italy, Tuscany, Reggello

Villa popularity 2024: 98% booked

This beautiful villa is situated in a splendid position inside a large estate owned by a famous family of Florentine entrepreneurs. The estate is located in a small, peaceful valley on the foothills of the Apennine mountains near the valley of the r... read more »

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Citycenter
Lowest week price
16
private pool
35 km
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