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Villas Gaiole in Chianti, Villas in Gaiole in Chianti as holiday homes

Properties by Type » Villas by Geographical Area » Chianti » Gaiole In Chianti

Villas in Gaiole in Chianti as holiday homes

Are you planning your holidays in Tuscany? Do not hesitate to contact us. We are an agency specialized in villas as holiday homes and we have selected the best villas in Chianti and in Tuscany. Here we offer villas in Gaiole in Chianti, sure that you will love this area in Tuscany. Besides our list of villas in Gaiole in Chianti, we have prepared also a brief introduction on this beautiful town.



The historic centre in Gaiole in Chianti is characterized by its beautiful square in a triangular shape. In the past, the town developed as a ‘mercatale’, a place for a market: the square, in fact, was the main place of encounter and exchange. Today when you arrive in the square in Gaiole in Chianti, you may want to visit the beautiful Church of San Sigismondo in neo-Gothic style.

The Castello di Brolio (Brolio Castle) is certainly one of the most important castles in this area. During your stay, enter inside the well preserved medieval walls and visit the castle of the year 1000 and the Chapel of St. James with its works of the fifteenth century. The architect Giuliano da Sangallo transformed the defensive castle in a magnificent residence and the Ricasoli family was able to skillfully create and carry out a winery. In the eighteenth century the wine Chianti Castello di Brolio was already known throughout Europe with contracts for monthly shipments of wine crates for noblemen in London and Amsterdam. In the nineteenth century it was Bettino Ricasoli at the Castle of Brolio to determine the types of grape used for Chianti Classico.

Not to missed, the Badia di Coltibuono is a Church surrounded by woods of White fir trees and there is also a 20-metre high and 7-metre wide cedar of Lebanon. The Abbey belonged to the Vallombrosan monks.

Choose one of the Villas in Gaiole in Chianti that you find below. Castles, abbeys and great wine are waiting for you!

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Our most requested holiday homes:
Castle Torre Chianti Castle Torre Chianti

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: 1277 € - max: 2128 €

Reviews 1
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Villa Ivano Villa Ivano

Luxury villa dating back to the 16th century between Florence and Arezzo, in Upper Valdarno. Sleeps 12, swimming pool, Internet connection, barbecue. Perfect for holidays in Tuscany at the discovery of Valdichiana, Casentino and Chianti regions.

7 days: min: 1915 € - max: 4150 €
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Villa Navigatore Villa Navigatore

Elegant villa in panoramic location in the heart of Chianti Classico, just a few kilometres from Gaiole in Chianti (Siena). Sleeps 8, heatable swimming pool, Finnish sauna, air conditioning, Internet connection. Possibility of organising wine tasting events, cooking lessons and wellbeing itineraries. Utmost peace and privacy.

7 days: min: 3240 € - max: 4860 €
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Villa Botticelli Villa Botticelli

Tuscan villa with pool near Radda in Chianti in the countryside of Chianti between Siena and Florence. Sleeps 10, Internet connection.

7 days: min: 1750 € - max: 2800 €

Reviews 6
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Villa Simona Villa Simona

Villa for vacation rentals in Siena countryside. 4+2 sleeping accommodations, swimming pool.

7 days: min: 1016 € - max: 1544 €

Reviews 2
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Villa Letizia Villa Letizia

Luxury villa with breathtaking view over Siena. 10+2 sleeping accommodations, swimming pool, satellite TV.

7 days: min: 3190 € - max: 4665 €
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Villa Greve in Chianti Villa Greve in Chianti

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: 1070 € - max: 1380 €
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Villa Zanobi Villa Zanobi

Independent house in an old hamlet in the Chianti Classico area, near the village of Gaiole in Chianti (Siena). Sleeps 8, swimming pool, wood-burning oven, children's playground with slide and swing, air conditioning.

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

Elegant villa in Upper Valdarno, between Montevarchi and Arezzo. Sleeps 10, swimming pool, private pond, barbecue, Internet connection. Ideal for relaxing holidays in the peaceful Tuscan countryside. Factory outlet of a famous fashion brand within a few kilometres.

7 days: min: 3190 € - max: 3725 €
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Farmhouse Pestello Farmhouse Pestello

Farmhouse with swimming pool in the heart of Tuscany, near Montevarchi (Arezzo) Sleeps 12, tennis/volleyball/basketball court, hydromassage, Internet connection, air conditioning. Possibility of organising cooking lessons and wine tasting events. Wonderful views over the valley of the River Arno and Pratomagno.

7 days: min: 2385 € - max: 4405 €

Reviews 1
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Farmhouse Sesta Farmhouse Sesta

Farmhouse dating back to the early 20th century situated in the countryside around Arezzo, a few kilometres from the Chianti region. Sleeps 8, wide fully fenced park, swimming pool, Internet connection.

7 days: min: 635 € - max: 2365 €

Reviews 1
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