
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 $175 NZD per night before taxes and fees

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Over 150 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
4.93 out of 5 average rating, 255 reviews
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.
4.97 out of 5 average rating, 106 reviews
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)
4.97 out of 5 average rating, 174 reviews
La Vignaccia (Farmhouse) - villa w/private pool
Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.
4.96 out of 5 average rating, 102 reviews
Il Vichiaccio: Florence Villa with Jacuzzi
Cozy Chianti Villa close to 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!
4.95 out of 5 average rating, 202 reviews
Villa La Doccia, Greve in Chianti
Villa La Doccia is located about an 8-minute drive 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 and peaceful area, on a small farm surrounded by vineyards and olive groves, where guests can enjoy nature and the typical Tuscan landscapes. The location is ideal for those who want to relax in the countryside but at the same time be close to the center of Greve in Chianti.
4.85 out of 5 average rating, 179 reviews
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.
5.0 out of 5 average rating, 17 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
4.98 out of 5 average rating, 107 reviews
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.
4.98 out of 5 average rating, 120 reviews
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.
5.0 out of 5 average rating, 190 reviews
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).
4.95 out of 5 average rating, 221 reviews
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.
4.89 out of 5 average rating, 309 reviewsPopular amenities for Castellina in Chianti villa rentals
Private villa rentals

Casanovina
4.92 out of 5 average rating, 12 reviews
Villa with pool in Chianti - Castellare Petroso
5.0 out of 5 average rating, 33 reviews
Tuscan Villa with private swimming pool
4.64 out of 5 average rating, 45 reviews
Luxury Villa on Chianti Wine Estate
4.93 out of 5 average rating, 96 reviews
Villa in Tuscany with a private panoramic pool
5.0 out of 5 average rating, 35 reviews
Country house with pool and garden by Vacavilla
4.85 out of 5 average rating, 26 reviews
Villa with pool in Chianti Area
4.95 out of 5 average rating, 73 reviews
Casa Faraona, villa with private pool
5.0 out of 5 average rating, 31 reviewsLuxury villa rentals

Poggio del Fattore-Villa with pool, hilltop, Chianti
4.99 out of 5 average rating, 131 reviews
Exclusive Tuscan Villa with private pool
5.0 out of 5 average rating, 16 reviews
Dream House in Tuscany, with Amazing View and Pool
4.82 out of 5 average rating, 72 reviews
Valluccia 51
5.0 out of 5 average rating, 50 reviews
romignano wine farm
4.74 out of 5 average rating, 57 reviews
L'Apparita del Peruzzi | Villa | Private Pool & A/C
5.0 out of 5 average rating, 22 reviews
Put down your luggage, this is just the beggining!
4.89 out of 5 average rating, 99 reviews
Tenuta Uzielli an elegant countryside villa
5.0 out of 5 average rating, 20 reviewsVilla rentals with a pool

Wine Experience Villa in Montepulciano
4.97 out of 5 average rating, 126 reviews
Coaching House
5.0 out of 5 average rating, 67 reviews
STUNNING 5BR VILLA WITH POOL IN CHIANTI TUSCANY
4.81 out of 5 average rating, 36 reviews
Villa il Balocco
4.98 out of 5 average rating, 43 reviews
[Le rondini in Tuscany] Exclusive View Pool Villa
4.92 out of 5 average rating, 25 reviews
The Villa of the Spendthrift Brigade!
5.0 out of 5 average rating, 28 reviews
Private Villa with semi-Olympic pool and Tennis
4.98 out of 5 average rating, 50 reviews
Chianti Tuscany: villa with a view
4.93 out of 5 average rating, 80 reviewsDestinations to explore
- House rentals Castellina in Chianti
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- Chalet rentals Castellina in Chianti
- Pet-friendly rentals Castellina in Chianti
- Cottage rentals Castellina in Chianti
- Rentals with pools Castellina in Chianti
- Villa rentals Tuscany
- Villa rentals Italy
- 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)
- Stazione Santa Maria Novella
- Cala Violina
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





