Gaiole in Chianti Gaiole in Chianti is a medieval city located along the Massellone river and probably named after “gaggiolo” which refers to a big forest. Due to its location, Gaiole has always been an important market centre for the castles and towns in the surrounding. Back in the days, Gaiole was next to being an important market centre also very important to the clergy. This can be traced back to the churches and monasteries that can be found in Gaiole. A church that must be visited is the Parish Church of Spaltenna; consisting of a monastery, church and cluster of farmhouses. Here a valuable 15th century crucifix can be found. A castle situated in this area, also highly recommended to visit is the Castello di Brolio, inhabited by the Ricasoli family since the 12th century, known for producing wine. It isn’t actually possible to enter the castle as descendants of the family still live there, however it is possible to visit the gardens. A wine shop can be found too on the property, offering wine tastings. Of course, the Chianti Classico wine is sold here, but it is also on offer in many other wineries in this region, such as the Abbey of Coltibuono. This former monastery is turned into a wine estate comprising a big forest with a cedar of Lebanon, with a circumference of as much as 7 meters. In order to find some traditional little shops, you must go to the main square where you’ll find a traditional Italian grocery store, an ice cream shop and a cute little pottery shop. Gaiole in Chianti can be reached by flying to Florence and from there taking the car.

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 6 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: 67% 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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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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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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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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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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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 »

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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 »

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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: 91% 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 »

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

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

Villa popularity 2024: 94% 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 »

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

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

Villa popularity 2024: 94% 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 »

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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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