Castellina in Chianti Rentals
From $102 per night (USD)VRBO
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The apartment Al Poggio Della Capannina in Castellina in Chianti is the perfect accommodation for a stress-free holiday ...
From $102 per night (USD)VRBO
From $678 per night (USD)VRBO
Casale Monte
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
The cottage in Castellina in Chianti has 6 bedrooms and has capacity for 12 people. The cottage is 480 m². The farmhouse ...
From $678 per night (USD)VRBO
From $100 per night (USD)VRBO
Our cottage, in the beautiful Tuscan countryside, not far from the cities of art
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Located in Barberino Tavarnelle, this welcoming vacation home brings it all within your reach. Let your feet make sho ...
From $100 per night (USD)VRBO
From $1895 per night (USD)Expedia
Villa Castellina located in an organic boutique winery,
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
<p>Located in Castellina in Chianti, this welcoming villa lets you experience it all. With the property's convenient ons ...
From $1895 per night (USD)Expedia
From $1574 per night (USD)VRBO
Luxury Villa W/ Panoramic Views & Private Pool
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
<p>Located in Castelnuovo Berardenga, this 7-bedroom, 7-bathroom villa lets you experience it all. Fans of nature and th ...
From $1574 per night (USD)VRBO
From $678 per night (USD)VRBO
Casale Santino
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
The cottage in Castellina in Chianti has 5 bedrooms and has capacity for 10 people. The cottage is 400 m². Casale Santin ...
From $678 per night (USD)VRBO
From $1208 per night (USD)VRBO
Charming Villa W/ Private Pool in Heart of Chianti
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 8
<p>Nestled in Radda in Chianti, this 8-bedroom, 4-bathroom villa brings it all within your reach. Fans of nature and the ...
From $1208 per night (USD)VRBO
From $450 per night (USD)Expedia
In The Heart Of Chianti, Pool, Wifi, View
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Situated in the heart of Chianti this property is rich in history and is in a privileged position offering panoramic vie ...
From $450 per night (USD)Expedia
From $513 per night (USD)VRBO
Beautiful villa for 10 guests with private pool, WIFI, A/C, TV and panoramic view
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Vacation rental In The Heart Of Chianti, Pool, Wifi, View - Lillia is a lovely property (400 sq m) that includes WiFi i ...
From $513 per night (USD)VRBO
From $1062 per night (USD)Expedia
Beautiful private villa with WIFI, private pool, TV, patio, pets allowed and panoramic view
- Bedrooms:
- 5
- Bathrooms:
- 9
- Sleeps:
- 23
Property Summary Fattoria Petraglia is a rustic farmhouse dating back to the 15th century, surrounded by trees, meadows, ...
From $1062 per night (USD)Expedia
From $921 per night (USD)VRBO
Fattoria Petraglia by Interhome
- Bedrooms:
- 5
- Bathrooms:
- 9
- Sleeps:
- 23
Monteriggioni: Rustic farmhouse "Fattoria Petraglia", detached from the 15th century, surrounded by trees, meadows and v ...
From $921 per night (USD)VRBO
From $10198 per night (USD)Expedia
Villa Castellina - Castellina in Chianti, Siena, Toscana
- Bedrooms:
- 11
- Bathrooms:
- 10
- Sleeps:
- 19
VILLA CASTELLINA - CHIANTI AREA Villa Castellina is a luxurious property overlooking the beautiful hills of the famous T ...
From $10198 per night (USD)Expedia
From $99 per night (USD)VRBO
Chalet in Chianti with swimming pool and tennis court
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
<p>Located in Castellina in Chianti, this welcoming vacation home brings it all within your reach. With convenient onsit ...
From $99 per night (USD)VRBO
From $1038 per night (USD)VRBO
Fattoria nel Chianti 14 In Castelnuovo Berardenga, Tuscany
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Property for exclusive use Classic manor, 380 sq. m., located in a farm in a panoramic location, with a large garden and ...
From $1038 per night (USD)VRBO
From $1521 per night (USD)VRBO
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this marvelous typical Tuscan stonehouse in picturesque Radda in Chianti. With 4 cozy bedrooms including 1 que ...
From $1521 per night (USD)VRBO
From $1181 per night (USD)Expedia
Holiday Home 'Badia a Passignano with Pool' with Shared Pool, Private Terrace and Wi-Fi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The holiday home Badia a Passignano with pool is located in Barberino Tavarnelle and is the ideal accommodation for a re ...
From $1181 per night (USD)Expedia
From $175 per night (USD)VRBO
Apartment Fonterutoli
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
'recently renovated apartment located in a medieval village between Siena and Castellina in Chianti Località Fonterutoli ...
From $175 per night (USD)VRBO
From $2341 per night (USD)Expedia
Exclusive Historic Villa & Vineyard -- Private Chef, Pool, Views, Tennis, & More
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Benvenuti a Villa Poggio alle Corti! Poggio alle Corti is an exclusive private villa and vineyard with breathtaking pan ...
From $2341 per night (USD)Expedia
From $255 per night (USD)VRBO
Stunning private villa with WIFI, A/C, TV and panoramic view, close to Greve In Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Property Villetta Cafaggio, Ac, Wifi, Panzano In Chianti is a lovely stone building (110 sq m) that includes WiFi inter ...
From $255 per night (USD)VRBO
From $1747 per night (USD)Expedia
Wonderful private villa with private pool, A/C, WIFI and terrace, close to San Gimignano
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Conveniently located 8 km (5 mi) from Castellina In Chianti, Italy in the tourist area "San Gimignano And Surroundings" ...
From $1747 per night (USD)Expedia
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Setriolo by Arceno Rentals Club, exclusive Villa and Annex, Pool A/C Concierge
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
SETRIOLO IS NEWLY ADVERTISED. FOR THE FIRST THREE RESERVATIONS RECEIVED A WINE TASTING WILL BE OFFERED COMPLIMENTARY BY ...
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From $410 per night (USD)Expedia
Stunning private villa for 8 guests with private pool, WIFI and TV, close to Siena
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Casa La Cedrina, Pool, Monteriggioni is a nice property (200 sq m) with private pool and WiFi internet. The property ca ...
From $410 per night (USD)Expedia
From $459 per night (USD)VRBO
Wonderful villa for 10 guests with A/C, WIFI, TV, patio and panoramic view
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Property Summary 'Terrazza sul Chianti' is a large, modern two-story house renovated in 2025, situated in Castellina In ...
From $459 per night (USD)VRBO
From $646 per night (USD)Expedia
Panoramic Chianti Villa with Private Pool & SPA - Castellare Petroso
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Castellare Petroso, where the Tuscan dream comes to life. This magnificent villa is located in the heart of C ...
From $646 per night (USD)Expedia
From $359 per night (USD)VRBO
Casa La Cedrina, Pool, Monteriggioni
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Independent house near Monteriggioni, immersed in the peace and colors of the Tuscan countryside, arranged over two leve ...
From $359 per night (USD)VRBO
From $2196 per night (USD)Expedia
Villa in Badia A Passignano with 6 bedrooms sleeps 14
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
Rinomia — Villa dei Corticelli A country retreat with boutique hotel services in the heart of Chianti Nestled among rows ...
From $2196 per night (USD)Expedia
From $1891 per night (USD)VRBO
Muricciaglia 14, Emma Villas
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
This rate includes: -Utilities: Electricity, water, gas for cooking purposes - weekly linen, initial and final cleaning ...
From $1891 per night (USD)VRBO
From $1002 per night (USD)VRBO
Villa Yasmin, elegant villa, in the heart of Chianti Classico
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
<p>Located in Castellina in Chianti, this welcoming villa brings it all within your reach. Jump into your car and make s ...
From $1002 per night (USD)VRBO
From $159 per night (USD)VRBO
Fattoria Petraglia - Loggiato by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Monteriggioni: Rustic farmhouse "Fattoria Petraglia", detached from the 15th century, surrounded by trees, meadows and v ...
From $159 per night (USD)VRBO
From $140 per night (USD)VRBO
Cellole - La Stalla by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residen ...
From $140 per night (USD)VRBO
From $3171 per night (USD)VRBO
Podere Palazzolo, ancient farmhouse nestled in the hills of Chianti Classico.
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 16
<p>Located in Castellina in Chianti, this 8-bedroom, 8-bathroom vacation home lets you experience it all. Fans of nature ...
From $3171 per night (USD)VRBO
From $397 per night (USD)Expedia
Terrazza sul Chianti by Interhome
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Castellina in Chianti: Large, modern house "Terrazza sul Chianti", 2 storeys, renovated in 2025. 2 houses in the residen ...
From $397 per night (USD)Expedia
From $5659 per night (USD)VRBO
Villa in Piazza with 11 bedrooms sleeps 20
- Bedrooms:
- 8
- Bathrooms:
- 11
- Sleeps:
- 20
Villa Cavresa — Chianti, The Villa At The Glance There is a moment, along the road that winds through the rows of Chiant ...
From $5659 per night (USD)VRBO