Luxury villas for rent in Tuscany

Castellina in Chianti

The centre of Castellina in Chianti built up area is the ancient fortress designed in the second half of the fifteenth century by the great architect Giuliano da Sangallo.


Castellina in ChiantiCastellina stands more than protected on its hilly bed. The village offers a series of patrician palazzos which are restored military garrisons built first by the associates of the counts Guidi who, originally from Garfagnana , pressed forward into the heart of Tuscany in the attempt to control it either diplomatically or militarily, and later by the Florentines who were constantly on their guard against the Sienese. The centre of the built up area is the ancient fortress designed in the second half of the fifteenth century by the great architect Giuliano da Sangallo.
In Via Ferruccio one gets the feeling of Castellina’s former opulence. Right at the end of this street, at the fork leading to the fortress, is the neo-Romanesque church of San Salvatore, rebuilt after being destroyed in the second world war.
A stop-off in Castellina may obviously include tasting at the numerous wine lodges, but you can also get to know the great art of Chianti pork-butchers whose charcuterie is highly prized for its unforgettable flavours.

Rocca di Castellina in ChiantiIf we want to find the origin of Castellina in Chianti we have to go far back to the beginning of history. These hills, sometimes wild, often softly rolling, still indicate that mankind has been using them for differenl purposes at least since the 7th century B.C. Towns and settlements founded during this period and located along the most important donkey tracks leading from the mountains down to Castellina in Chianti, are stil] proof of a communication link between the large Mediteranian Etruscan cities like Vulci, Vetulonia and Roselle, as well as the famous tradin' centers of the North like Spina.
Since the 1 3th century A.D. Castellina is part of the "Lega del Chianti", meaning "Chianti Alliance". This was a administrative and military alliance within the state of Florence. Because of its optimal strategic location which guaranteed the control of all surrounding roads, as well as the whole valley of the Elsa river, Castellina retained its military position.
Proof of this is the existence of the imposing fortress, nowadays used by the local town govemment. Castellina was once surrounded by mighty walls and smaller towers, only two gates intermpted the closed defence line. One pointed towards Siena, the other towards Florence. Unfortunately both gates were completely destroyed (the gate towards Florence was destroyed during battles in the second World War). Parts of the defending walls can shall be seen today. Unfortunately most parts have been covered over or been integrated into the later construction of houses.
In 1483 Castellina was once again retumed to the Medici. Due to the surrender of Siena to the troops of Karl Vin April 1555 and the following ammexation of the State of Siena, Castellina in Chianti lost its strategic importance and became a part of the dominion of the Grand Duchy of Toscany.


Castellina in Chianti: discover the surroundings

  • Chianti museums Chianti museums (7 km)
    Chianti museums: Museo di Arte Sacra of Impruneta, Basilica di Santa Maria of Impruneta, Museo di Santa Maria sul Prato of San Casciano val di Pesa, Museo di San Cascinao
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  • Chiantishire Chiantishire (7 km)
    The Chianti territory with its hilly countryside of incomparable beauty lies in the heart of Tuscany.
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  • Radda in Chianti Radda in Chianti (7 km)
    Radda in Chianti is the vineyard village. From the high ground on which it was built in the middle ages, between the waters of the rivers Arbia and Pesa, you gaze over a very dense interweave of vineyards.
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  • Monteriggioni Monteriggioni (10 km)
    Monteriggioni is without doubt one of the most classical and best known Italian walled town.
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  • Poggibonsi Poggibonsi (11 km)
    Poggibonsi rises nearby the confluence of the Staggia torrent in the Elsa river, along the valley dividing the region of the Chianti by the Colline Metallifere.
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  • Staggia castle Staggia castle (11 km)
    The walls of Staggia castle in Poggibonsi join the castle on the northern side and are today almost intact, with the exception of two short interruptions.
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  • Brolio Castle Brolio Castle (12 km)
    The Brolio castle has a Longobard origin, although today of the ancient original small fortress remain only the location.
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  • Meleto castle Meleto castle (12 km)
    Like in a fairytale, the Castle of Meleto stands out in the enchanting Chianti landscape at the end of a nice avenue lined with cypress-trees and junipers, in the middle of sun-kissed fields and vineyards.
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  • Gaiole Gaiole (12 km)
    Gaiole in Chianti has developed along the valley of the River Massellone due to its idea position as a trading and meeting point and its origins are based in these very geographical characteristics.
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  • Barberino Val D'elsa Barberino Val D'elsa (12 km)
    A winding hilly road, once the ancient Via Cassia and now State road n° 2, leads up to the town of Barberino Val d’Elsa, situated high up above the valley.
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  • Greve in Chianti Greve in Chianti (13 km)
    In the ancient times, Greve in Chianti was a small built-up area of the territory called "Agro di Florentia", even if expert and researchers of the Etruscan civilization claim that it can date back to a previous century.
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  • Colle Val D'Elsa Colle Val D'Elsa (15 km)
    Colle di Val d'Elsa is located in the heart of Tuscany, in a strategic position, close to the cities of Siena, Florence and Volterra, along the route of the old Via Francigena
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  • Valdelsa Valdelsa (15 km)
    Val d'Elsa is located in the heart of Tuscany, in a strategic position near the cities of Siena, Florence and Volterra.
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  • SentierElsa SentierElsa (15 km)
    The way down is located to the left of the bridge of San Marziale, as one stands with one's back to Colle di Val d'Elsa.
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  • Siena Siena (17 km)
    Founded by the Etruschis, Siena was Roman colony to the time of August.
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  • Travel Siena Travel Siena (17 km)
    A way of travelling that priviledges direct contact with nature in order to capture emotions and discover the Terre di Siena furthest corners.
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Accommodations in the area


    • Greve in Chianti (Florence)
    • 14 km from Castellina in Chianti

    Villa Chianti 7 beds

    Villa Chianti is a private villa for rent in Chianti area with pool and garden that can accommodate up to 7 people.
    An oasis of peace and tranquility with views of the Chianti valleys not far from the main tourist attractions of Tuscany.

    Availability request


    • Bagno a Ripoli (Florence)
    • 30 km from Castellina in Chianti

    Villa Valdarno 12 beds

    Villa Valdarno is a typical Tuscan farmhouse located in a secluded and peaceful area in the heart of the Tuscan countryside, among vineyards and olive groves, and enjoys a privileged panoramic view of the Florentine Valdarno.
    The ideal solution for groups of friends or acquaintances who wish to spend their holidays in Tuscany with the comforts of a detached villa with swimming pool and large garden.

    Availability request


    • Lucca (Lucca)
    • 77 km from Castellina in Chianti

    Historic Villa Lucca 12 beds pool

    Historic villa 14 km from the center of Lucca immersed in the green of the Tuscan vineyards and olive groves, it has a private swimming pool and a large park.
    Set on 350 square meters in a dominant position offers a unique view of the hills of Tuscany.

    Availability request


    • Castiglione della Pescaia (Grosseto)
    • 86 km from Castellina in Chianti

    Villa Roccamare Castiglione della Pescaia 12 beds

    Beautiful and characteristic villa with stone finishes located in the exclusive Roccamare area in Castiglione della Pescaia.
    Surrounded by the green of the pine forest and the total privacy with 2000 sqm park equipped with relaxation area and barbecue is located about 400 meters from the sea and has a private beach.

    Availability request


    • Castiglione della Pescaia (Grosseto)
    • 86 km from Castellina in Chianti

    Villa Punta Ala 9 beds pool

    Beautiful villa with swimming pool surrounded by greenery and tranquility of the exclusive tourist destination Punta Ala and small attic used as service personnel only 300 meters from the sea of Tuscany.
    This ideal solution for those who want to spend their holidays near the beautiful sea of Punta Ala with the comforts of an exclusive villa.

    Availability request


    • Massarosa (Lucca)
    • 88 km from Castellina in Chianti

    Stone Farmhouse Massarosa 8 beds pool

    Stone farmhouse in typical Tuscan style skilfully and elegantly renovated in a dominant position on the hills of Massarosa with spectacular views that reach the sea of Tuscany. The farmhouse has a swimming pool with whirlpool.
    Perfect solution for those that search the real authentic Tuscany staying in the hills but not far from the Versilia sea.

    Availability request


    • Viareggio (Lucca)
    • 90 km from Castellina in Chianti

    Villa Torre del Lago 5 beds

    Typical Tuscan farmhouse for rent in Torre del Lago, Massaciuccoli area with 3 bedrooms and 5 beds, just 1 km from the Tuscany coast.
    Ideal solution for small groups or families looking for a villa for rent not far from the sea in a context of absolute privacy.

    Availability request


    • Massarosa (Lucca)
    • 91 km from Castellina in Chianti

    Farmhouse Massarosa 14 beds pool

    Beautiful ancient Tuscan farmhouse completely renovated located on Tuscan hills 10 km from the golf course of Versilia. The villa can accommodate up to 14 people.
    An oasis of peace for those looking for a stay in the Tuscan hills while staying close to the sea. Perfect for a relaxing holiday in close contact with nature.

    Availability request


    • Camaiore (Lucca)
    • 92 km from Castellina in Chianti

    Charming villa Tuscany coast 14 beds pool

    Eighteenth-century villa located in a picturesque area of the Tuscan hills at the foot of the Apuan Alps, the villa has a park with swimming pool and tennis court.
    The spacious suites of the villa embellished with charming details and enhanced by modern comforts will make your stay an unforgettable experience.

    Availability request


    • Camaiore (Lucca)
    • 93 km from Castellina in Chianti

    Villa Pieve di Camaiore 8 beds pool

    Luxury and charming villa with swimming pool for rent surrounded by the green hills of Camaiore not far from the sea of the Tuscan coast.
    The villa is ideal for those looking for an oasis of absolute peace and relaxation guaranteed by the elevated position and the external fence in style.

    Availability request


    • Camaiore (Lucca)
    • 93 km from Castellina in Chianti

    Villa Prato di Sopra Camaiore 10 beds pool

    This villa is really some thing special, perched on the top of a hill the views are endlessly breath taking.
    This villa is really some thing special, perched on the top of a hill the views are endlessly breath taking.

    Availability request


    • Camaiore (Lucca)
    • 93 km from Castellina in Chianti

    Villa Camaiore Hills 10 beds pool

    Villa located 3 km from the center of Camaiore in a quiet and sunny position 10 km from Tuscan sea.
    Ideal for those looking for a villa accommodation on the hills of Versilia a few miles from Tuscan sea.

    Availability request


    • Camaiore (Lucca)
    • 93 km from Castellina in Chianti

    Restored Farmhouse Camaiore 9 beds pool

    Beautiful fully restored farmhouse located on the hills of Camaiore. The villa is surrounded by a park of 2500 square meters in which is inserted the beautiful pool.
    Thanks to the dominant position on the valley from the farmhouse you can enjoy a beautiful 360 ° panoramic view.

    Availability request


    • Camaiore (Lucca)
    • 93 km from Castellina in Chianti

    Villa Camaiore Hills 7 beds pool

    Wonderful villa with swimming pool surrounded by greenery, tranquility and privacy of the Pieve di Camaiore about 10 km from the sea of the Tuscan coast.
    The villa has all the comforts necessary to ensure an unforgettable stay in Tuscany and is the ideal solution for small groups up to 7 people who want to stay in the countryside but not far from the sea of Versilia.

    Availability request


    • Massarosa (Lucca)
    • 95 km from Castellina in Chianti

    Villa Massarosa 10 beds pool

    Beautiful and spacious villa in the countryside located in the hills of Versilia, 3 km from the golden beaches of the Tuscan coast with private pool and park.
    Perfect solution to stay in the green hills of Tuscany, 3 km from the golden beaches of Versilia

    Availability request