
Villa holiday rentals in Castellina in Chianti
Find and book unique villas on Airbnb
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

Wine Experience Villa in Montepulciano
🏡 Villa Talosa è immersa nei vigneti della Fattoria della Talosa, storica azienda vitivinicola di Montepulciano produttrice di Vino Nobile. Un luogo autentico, ideale per rilassarsi con la magia della campagna toscana e una vista incantevole da ogni finestra. A soli 1,5 km dal centro storico, raggiungibile anche a piedi, potrete visitare la nostra Cantina Storica del 1500 sotto Piazza Grande: un’esperienza unica tra storia, passione per il vino. Riscaldamento e aria condizionata sono inclusi.

Tuscany Country House Villa Claudia
Vivi l’incanto della nostra Country House: un antico casale toscano di pregio, finemente restaurato, con vista mozzafiato sul borgo di Canneto (785 d.C.). Immersa nel verde di San Miniato e dotata di ogni lusso moderno, la villa è un rifugio esclusivo per rigenerarsi. Scegli tra il relax totale nella Jacuzzi in giardino, tour enogastronomici d'eccellenza o visite alle vicine città d’arte toscane. Un’esperienza sensoriale indimenticabile tra storia e natura. Prenota il tuo sogno in Toscana!

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.

Il Vichiaccio: Accessible Chianti Villa & Jacuzzi
Cozy Chianti getaway 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!

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.

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.

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).

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.

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Quite old farmhouse on the hills of Florence
Two levels 800th rustic country house, on the hills surrounding the town with original forniture and a stunning view of the facing valley, a beautiful patio and large garden. 25 min driving from center, well placed for Chianti area, Siena, San Gimignano. 1hr driving to Pisa, Lucca, Volterra, Arezzo, Cortona and much more! Possible to have cooking class or dinners with my personal chefs Mirella and Stefano!

"Villa Daisy" overlooking Siena
Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).
Popular amenities for villa rentals in Castellina in Chianti
Private villa rentals

Luxury Villa on Chianti Wine Estate

Villa Siveri - private swimming pool - air con

Valluccia 51

farmhouse Il Poggino house Stella

Montemarcoli

Casa Colombaia, in the Chiantishire

Lucignano Secondo – La Villa

CasaDiManuela:TotallyPrivateChiantiVilla withTub
Luxury villa rentals

Villa with pool in Chianti Area

Romantic Villa with private pool - "Il Pollaio"

Casa de' Miei – Garden Villa near Florence, Chianti

Stone house with private pool Vacavilla Exclusive

[Le rondini in Tuscany] Exclusive View Pool Villa

Villetta dei Fagiani - pools, Jacuzzi in Florence

Villa Poggio in Mandria in Chianti

Private Villa with semi-Olympic pool and Tennis
Villa rentals with a pool

Tuscan villa in Chianti Classico hills Il Poggiolino

Villa Angiolina

La Cipresseta Estate | Cipresso House

San Giovanni in Poggio, Villa Meriggio 95 sqm

Charming Tuscan retreat: spa, pool & cinema

CHARMING TUSCANY VILLA PRIVATE POOL

Private Villa in Chianti between Florence & Siena

Villa La Poggerina, private pool and amazing view
Quick stats about villa rentals in Castellina in Chianti

Nightly prices starting at
Castellina in Chianti holiday rentals start at $128 SGD per night before taxes and fees

Verified guest reviews
Over 140 verified reviews to help you choose

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
Destinations to explore
- Flat rentals Castellina in Chianti
- Rentals with a patio Castellina in Chianti
- Chalet rentals Castellina in Chianti
- Pet-friendly rentals Castellina in Chianti
- Cottage rentals Castellina in Chianti
- House rentals Castellina in Chianti
- Rentals with a washing machine and dryer Castellina in Chianti
- Family-friendly rentals Castellina in Chianti
- Rentals with outdoor seating Castellina in Chianti
- Rentals with pools Castellina in Chianti
- Rentals with a fireplace Castellina in Chianti
- Villa rentals Tuscany
- Villa rentals Italy
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Stazione Santa Maria Novella
- Lake Trasimeno
- Piazza del Duomo (Pisa)
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Pisa Centrale Railway Station
- Cala Violina
- Mercato Centrale
- Fortezza da Basso
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Uffizi Gallery
- Del Chianti
- Mugello Circuit
- Piazzale Michelangelo
- Pitti Palace
- Palazzo Vecchio
- Spiagge Bianche
- Boboli's Garden
- Parco delle Cascine
- Basilica of Santa Croce





