
Villa holiday rentals in Castellina in Chianti
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Quick stats about villa rentals in Castellina in Chianti

Nightly prices starting at
Castellina in Chianti holiday rentals start at $127 SGD per night before taxes and fees

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Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Castellina in Chianti rentals

4.5 Average rating
Castellina in Chianti stays receive an average rating of 4.5 out of 5 from guests
Top-rated villa rentals in Castellina in Chianti
Guests agree: these villas are highly rated for location, cleanliness and more.

Manor House - IlVillinoFarmhouse
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area
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CasaDiManuela:TotallyPrivateChiantiVilla withTub
CasaDiManuela:TotallyPrivateVilla in Chianti withTub Jacuzzi The villa, immersed in the Chianti countryside, was obtained from an old farmhouse and then renovated with extreme care and attention to detail. Original terracotta floors and ceilings with ancient exposed beams, old traditional Tuscan furniture, flowery fabrics that dress beds and armchairs, paintings, antique china and lived objects recovered from markets and junk dealers will frame your living room. Nothing here is by chance.
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Villa of the 2 Olive Trees (Abbadia Isola)
FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)
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Villa with pool in Chianti - Castellare Petroso
Located in the heart of the Chianti Classico region, among vineyards and woods, Castellare Petroso offers an authentic Tuscan experience, simple and elegant. The marlstone villa is surrounded by a fenced park of over 5 hectares, ensuring maximum privacy and relaxation. An automatic gate at the main entrance welcomes guests to this unique setting, where the architecture blends into the beautiful, untamed landscape. An exclusive retreat for those looking for the real Tuscany.
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Villa La Doccia, Greve in Chianti
Villa La Doccia is located approximately 8 minutes by car from the center of Greve in Chianti, in the area of Casole, in the heart of the beautiful Chianti countryside. The villa is located in a quiet, peaceful area on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the characteristic Tuscan landscape. The location is ideal for those who want to relax in the countryside while still being close to the center of Greve in Chianti.
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THE CASTELLACCIO CYPRESSES (Cip 1 + Cip 2)
Barn and stone house with swimming pool and stunning views in Chianti Classico The Cipressini del Castellaccio are ancient stone houses, originally agricultural annexes to the main farmhouse dating back to the seventeenth century located in the heart of the Chianti Classico on the side of a slope with a breathtaking view of the Val d.Elsa. Luxuriously renovated and furnished, equipped with every comfort, they are located in such a way as to guarantee absolute privacy.
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Il Vichiaccio: Florence Villa with Jacuzzi
Cozy Chianti Villa near Florence. This 135sqm stone house has a rustic kitchen with a fireplace. It sleeps 9 guests in 3 rooms, but for groups of 11, a 4th bedroom is included. Smaller groups can add it for extra comfort (extra fee). Enjoy the private garden with a covered dining area, a patio with armchairs and parking. The ground floor is fully wheelchair-friendly (kitchen, bedroom, bath). Plus, A/C and a private Jacuzzi (extra fee) for relaxing under the stars!
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Luxury Villa in the very heart of Chianti
The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.
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The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.
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Casanovina
Casanovina is a beautiful holiday villa in the Chianti region, set on an open ridge with spectacular views over the typical Chianti Classico landscape. Just a few hundred meters away is the renowned winery Castellare di Chianti, and the charming village of Castellina in Chianti can be reached in about 25 minutes on foot. This property is perfect for a large family or a group of friends wanting to spend relaxed days together.
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Farmhouse in Chianti
Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).
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Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
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Popular amenities for villa rentals in Castellina in Chianti
Private villa rentals

Luxury Villa on Chianti Wine Estate
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Country house with pool and garden by Vacavilla
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Sestuccia
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Villa in Tuscany with panoramic private pool
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Villa with pool in Chianti Area
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Tuscan Villa with private swimming pool
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Podere il Trebbio
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Luxury Villa in Chianti • Private Natural Pool
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Luxury villa rentals

La Vignaccia (Farmhouse) - villa w/private pool
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Exclusive Tuscan Villa with private pool
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Lucignano Secondo – La Villa
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Put down your luggage, this is just the beggining!
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The Villa of the Spendthrift Brigade!
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romignano wine farm
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Villa San Martino 6-8 people
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Romantic Villa with private pool - "Il Pollaio"
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Villa rentals with a pool

Wine Experience Villa in Montepulciano
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Coaching House
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Villa il Balocco
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Montemarcoli
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Villa La Poggerina, private pool and amazing view
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Villa Gelsomino, your dream in Tuscany
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[Le rondini in Tuscany] Exclusive View Pool Villa
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Panoramic villa in Crete Senesi, overlooking Siena.
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Destinations to explore
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- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Stazione Santa Maria Novella
- Mugello Circuit
- Mercato Centrale
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





