
Radda in Chianti Rentals

- From $173 per night (USD)
VRBO
La Casanova, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
This charming single-storey stone cottage clings to a south-facing hillside, offering fabulous views of the surrounding ...
From $173 per night (USD)VRBO
- From $187 per night (USD)
Expedia
Casetta con Vista, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $187 per night (USD)Expedia
- From $303 per night (USD)
VRBO
Il Boschetto, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Set across the first floor of a large stone farmhouse, this villa in rural Chianti offers comfortable lodgings for six p ...
From $303 per night (USD)VRBO
- From $187 per night (USD)
Expedia
Scorpione, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $187 per night (USD)Expedia
- From $86 per night (USD)
VRBO
Ulivo, Ceperano, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Ceperano stands among vineyards of native grapes that slope up a 1 Km walk to Radda in Chianti. Crafted with local stone ...
From $86 per night (USD)VRBO
- From $144 per night (USD)
Expedia
Girasole, Ceperano, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ceperano stands among vineyards of native grapes that slope up a 1 Km walk to Radda in Chianti. Crafted with local stone ...
From $144 per night (USD)Expedia
- From $203 per night (USD)
VRBO
La Taverna, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $203 per night (USD)VRBO
- From $299 per night (USD)
Expedia
Angolino, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away at the end of a quiet road, yet barely a mile from Radda, one of Chianti’s main market towns, Angolino is a ...
From $299 per night (USD)Expedia
- From $177 per night (USD)
VRBO
Limoni, Ceperano, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ceperano stands among vineyards of native grapes that slope up a 1 Km walk to Radda in Chianti. Crafted with local stone ...
From $177 per night (USD)VRBO
- From $203 per night (USD)
Expedia
Bacco, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $203 per night (USD)Expedia
- From $292 per night (USD)
VRBO
Casa di Pesa, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A really pretty villa built of light Tuscan stone, Casa di Pesa is set in expansive gardens on a wine estate (www.carmaw ...
From $292 per night (USD)VRBO
- From $504 per night (USD)
Expedia
Il Solatio, Cavriglia, Arezzo and Cortona
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
See Chianti and sigh. Il Solatio offers one of the most exquisite views of this classical landscape, with olive groves s ...
From $504 per night (USD)Expedia
- From $636 per night (USD)
VRBO
Calafralina, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Calafralina is a wonderful stone villa set in the heart of Chianti. Comprising a main house and a cluster of cottages, i ...
From $636 per night (USD)VRBO
- From $518 per night (USD)
Expedia
Villa Beba, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
If you've got a larger group of family or friends that you'd like to share the best of Tuscany with - and you dream of e ...
From $518 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Pergola, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $225 per night (USD)VRBO
- From $370 per night (USD)
Expedia
Poggio della Villa, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Arrive at this delightful stone-built villa on the edge of the Chianti town of Radda and you will quickly shake off any ...
From $370 per night (USD)Expedia
- From $865 per night (USD)
VRBO
Private Villa with WIFI, private pool, A\/C, TV, patio, pets allowed, panoramic view, parking
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
Property Summary Casale il Poggino is a charming vacation rental located in the heart of the Chianti Classico, perched o ...
From $865 per night (USD)VRBO
- From $146 per night (USD)
Expedia
Ancient stone farmhouse on a top of Chianti Hill with private garden and lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets ...
From $146 per night (USD)Expedia
- From $203 per night (USD)
VRBO
Stone Farmhouse in Chianti Hill between Florence, Siena private veranda and lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets ...
From $203 per night (USD)VRBO
- From $170 per night (USD)
Expedia
Farmhouse 15th century in Chianti with private garden and lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets ...
From $170 per night (USD)Expedia
- From $154 per night (USD)
VRBO
Ancient house in Chianti Hills with private lake and garden
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets ...
From $154 per night (USD)VRBO
- From $332 per night (USD)
Expedia
Villa \"San Bartolomeo\" with Pool and Wi-Fi - Pets allowed
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa San Bartolomeo is located in Castellina in Chianti, 20 km from Siena, and boasts beautiful views of the hills. The ...
From $332 per night (USD)Expedia
- From $747 per night (USD)
VRBO
Castellare Petroso, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Castellare Petroso sits on the Etruscan settlement site beneath the ancient hamlet of Colle Petroso. The villa is a reco ...
From $747 per night (USD)VRBO
- From $131 per night (USD)
Expedia
Le Bonatte by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Typical Tuscan stone farmhouse IT5292.850.1 and annex IT5292.850.3 50 m away, situated in the heart of Chianti Classico. ...
From $131 per night (USD)Expedia
- From $863 per night (USD)
VRBO
Casale Il Poggino by Interhome
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
Casale il Poggino, located in a hilly position in the heart of the Chianti Classico, consists of two units, the farmhous ...
From $863 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Farmhouse in the heart of the real chiantishire
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Farmhouse in the heart of Chiantishire at 3 kms minutes distance from the historical township of Castellina in Chianti. ...
From $175 per night (USD)Expedia
- From $344 per night (USD)
VRBO
Le Bonatte by Interhome
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Typical Tuscan stone farmhouse IT5292.850.1 and annex IT5292.850.3 50 m away, situated in the heart of Chianti Classico. ...
From $344 per night (USD)VRBO
- From $378 per night (USD)
Expedia
Private Villa with A\/C, private pool, WIFI, TV, patio, pets allowed, panoramic view, parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Property Summary Villa del Poggio is a rustic single-family house located in the peaceful countryside just 2 km from the ...
From $378 per night (USD)Expedia
- From $3339 per night (USD)
VRBO
VILLA CHIANTI RUBINO
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 14
Set in the very heart of Chianti Classico, this wonderful Villa, once the place where the estate produced and stored it ...
From $3339 per night (USD)VRBO
- From $132 per night (USD)
Expedia
detached villa with private pool and garden
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
<p>Located in a rural area, this welcoming vacation home lets you experience it all in Castellina in Chianti. There's co ...
From $132 per night (USD)Expedia
- From $211 per night (USD)
VRBO
Dionisia, Capannole, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled between vine covered hills, Capannole is a peaceful hamlet of eleven private houses which date back to 1400. A f ...
From $211 per night (USD)VRBO
- From $329 per night (USD)
VRBO
House with character
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Godenano di Mezzo is an ancient farm located in the heart of the Castellina in Chianti countryside, in the cradle of the ...
From $329 per night (USD)VRBO
- From $449 per night (USD)
VRBO
Le Bonatte by Interhome
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
The Le Bonatte farm located in the heart of the Chianti Classico is made up of two real estate units (the farmhouse and ...
From $449 per night (USD)VRBO
- From $1005 per night (USD)
Expedia
Villa Aryanna - Tuscan Countryside Villa with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
VILLA ARYANNA - SIENA AREA Villa Aryanna is a lovely Tuscan style villa located in the Chianti wine producing region of ...
From $1005 per night (USD)Expedia
- Click For Pricing
VRBO
\"DARIO4\" APARTMENT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The position overlooking the private furnished garden conveys into the Casa Dario 4 apartment all the fragrances of the ...
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- Click For Pricing
Expedia
\"DARIO3\" APARTMENT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Casa Dario 3 apartment is perfect for those traveling with the family or with a couple of friends. In its outdoor ga ...
Click For PricingExpedia
- Click For Pricing
VRBO
HOUSE \"BARN. 2\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ideal for those who love traveling with family or friends, the Casa Granaio 2 apartment offers hospitality, elegance and ...
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- Click For Pricing
Expedia
\"LA CAPANNA\" APARTMENT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Surrounded by nature and in a secluded position with respect to the other apartments, La Capanna is an independent house ...
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VRBO
\"PERA 3\" APARTMENT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Casa Pera 3 apartment, decorated in a country-chic style, is perfect for groups of friends or couples with several c ...
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Expedia
\"IL TORRINO\" APARTMENT
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Staying in a real medieval watchtower restored according to the origin interior design is an experience only Borgo di Pi ...
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- Click For Pricing
VRBO
\"PERA 4\" APARTMENT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The large wooden canopy bed and the numerous views of the Tuscan countryside will make you fall in love with the Casa Pe ...
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Expedia
HOUSE \"GUARD 1\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Casa Guardia 1 apartment, obtained from the ancient home of the Borgo gamekeeper, has the distinctive feature of off ...
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VRBO
HOUSE \"GUARD N. 2\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect for a group of friends or for a couple with children, the Casa Guardia 2 apartment maintains all the charm of th ...
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- Click For Pricing
Expedia
\"PERA 2\" APARTMENT
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In the living room with rustic brick arches and exposed beams, you can spend pleasant evenings in front of the fireplace ...
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- Click For Pricing
VRBO
\"DARIO 2\" APARTMENT
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Rustic charm and valuable materials characterize the Casa Dario 2 apartment which, thanks to its triple facilities, is s ...
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Expedia
CASA DARIO APARTMENT 5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The kitchen with the large and original fireplace and the delightful mezzanine which houses the sofa and TV, together wi ...
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- Click For Pricing
VRBO
HOUSE \"BARN. 1\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Brightness, soft colors and warm and hospitable furnishings will welcome you in the Casa Granaio 1 apartment, located on ...
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- Click For Pricing
Expedia
APARTMENT \"DARIO1\"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
If you want a romantic setting in which to relax in the total peace and quiet of the Chianti countryside, the Casa Dario ...
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- Click For Pricing
VRBO
\"PERA1\" APARTMENT
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Let yourself be enchanted by the romantic atmosphere of the Casa Pera 1 apartment, obtained within the old school of the ...
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- From $154 per night (USD)
Expedia
Stunning private villa with WIFI, private pool, TV, terrace, panoramic view and parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Property Summary Caiano is a charming and rustic vacation rental located in the heart of Tuscany, 750 meters above sea l ...
From $154 per night (USD)Expedia
- From $251 per night (USD)
VRBO
Antica Posta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Take a break with friends in the heart of Chianti at this superbly located villa. It’s just a few kilometres to Castelli ...
From $251 per night (USD)VRBO
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Expedia
The Villa
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Casa al Monte is an ancient peasant residence located on the top of a hill, surrounded by olive and fruit trees. It is l ...
Click For PricingExpedia
- From $1007 per night (USD)
VRBO
Villa Tregole, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
The vine-clad hills of Chianti are the classic image of Tuscany and the beautiful backdrop for Villa Tregole. Here in th ...
From $1007 per night (USD)VRBO
- From $763 per night (USD)
VRBO
Villa Arnica A: A characteristic and welcoming ancient tuscan country house surrounded by vineyards and olive groves, with Free WI-FI.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa Arnica A is a characteristic and welcoming ancient tuscan country house surrounded by vineyards and olive groves. ...
From $763 per night (USD)VRBO
- From $668 per night (USD)
VRBO
Casa al Monte In Greve in Chianti - Tuscany
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 14
Property for exclusive use Property at exclusive use. Tuscan farmhouse (400 sq. m.) with private swimming pool and Jacuz ...
From $668 per night (USD)VRBO
- From $5279 per night (USD)
Expedia
Villa Radda - 11 Guests
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 11
VILLA RADDA - FLORENCE AREA With its beautiful medieval tower set up as a wine bar, the villa offers spectacular views a ...
From $5279 per night (USD)Expedia
- From $279 per night (USD)
VRBO
Vacation home Olivo by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Country house "Olivo", detached, renovated in 2020. 500 m from the centre of Castellina in Chianti, 26 km from the centr ...
From $279 per night (USD)VRBO
- From $4815 per night (USD)
VRBO
Villa Pianvecchio by Fantasia Villas
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Pianvecchio is a charming, panoramic villa in the rolling hills of Radda in Chianti which looks out over vineyards and o ...
From $4815 per night (USD)VRBO
- From $1306 per night (USD)
VRBO
Villa Montemaggio by Fantasia Villas
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Montemaggio homestead, completely rebuilt, is in the heart of the Chianti, like an antique tower dominating the sple ...
From $1306 per night (USD)VRBO
- From $4796 per night (USD)
VRBO
Villa Castiglioni by Fantasia Villas
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
Castiglioni is a charming, panoramic villa in the rolling hills of Radda in Chianti which looks out over vineyards and o ...
From $4796 per night (USD)VRBO
- From $115 per night (USD)
VRBO
Panorama, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $115 per night (USD)VRBO
- From $258 per night (USD)
Expedia
Lavanda, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $258 per night (USD)Expedia
- From $420 per night (USD)
VRBO
Wonderful villa, family friendly. infinity pool, A\/C bedrooms, 6\/12 people
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Surrounded by Sangiovese vineyards and ancient olive groves, Casino de Sala is a small picturesque farm within walking d ...
From $420 per night (USD)VRBO
- From $318 per night (USD)
Expedia
Private Villa with private pool, A\/C, WIFI, TV, patio, pets allowed, panoramic view, parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Property Summary Nestled in a secluded and quiet area, the newly renovated Country house "Olivo" is a charming and detac ...
From $318 per night (USD)Expedia
- From $260 per night (USD)
VRBO
Holiday apartment Vagliagli for 1 - 6 persons with 2 bedrooms - Farmhouse
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
ED Refnr. 2899840 Castle in the Chianti, near Siena, nice location, quiet These holiday apartments in Tuscany are pa ...
From $260 per night (USD)VRBO
- From $97 per night (USD)
Expedia
The Porchereccia delle Bartaline
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The apartment is located within our farm just steps from Panzano. It is newly renovated and well cared for in details, c ...
From $97 per night (USD)Expedia
- From $168 per night (USD)
VRBO
Belvilla by OYO Uva
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This 2-bedroom farmhouse situated in Radda In Chianti is subtle for a small group or family. Resting in Tuscany, Italy, ...
From $168 per night (USD)VRBO
- From $4409 per night (USD)
Expedia
Luxury Villa in Tuscany for 10 People
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 10
Every season is perfect for a trip to Chianti, that hilly area of Tuscany world famous for its picturesque landscapes an ...
From $4409 per night (USD)Expedia
- From $189 per night (USD)
VRBO
Belvilla by OYO Limone
- Bedrooms:
- 6
- Bathrooms:
- 2
- Sleeps:
- 6
Situated in Radda In Chianti, Tuscany, Italy, this 2-bedroom farmhouse is ideal for families and groups with pets. Ideal ...
From $189 per night (USD)VRBO
- From $1405 per night (USD)
VRBO
FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 13
Set in the heart of the magical Chianti Classico region, this wonderful 6 BD – 6 BA Villa dates back to the 15th century ...
From $1405 per night (USD)VRBO
- From $1333 per night (USD)
VRBO
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
<p>Close to ecotours, cycling, and more, this family-friendly villa brings it all within reach. With convenient covered ...
From $1333 per night (USD)VRBO
- From $131 per night (USD)
Expedia
Casa Chiara by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Modern house "Casa Chiara", 2 storeys, built in 2009. 300 m from the centre of Castellina in Chianti, in a sunny positio ...
From $131 per night (USD)Expedia
- From $2271 per night (USD)
VRBO
Private and Peaceful Medieval Villa in the heart of Chianti
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 18
Tenuta di San Giusto; a very peaceful and characteristic villa dated from the year 1000. Situated in the municipality of ...
From $2271 per night (USD)VRBO
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Expedia
Case Domine, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Looking for splendid isolation? You’ll find it at this very private villa, alone among the vineyards of Chianti Classico ...
Click For PricingExpedia
- From $494 per night (USD)
VRBO
Villa Beba In Castellina in Chianti, Tuscany
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Property for exclusive use Historical 18th Century villa with outbuilding, on two floors, 340 sq. m. with 5 double bedro ...
From $494 per night (USD)VRBO
- From $266 per night (USD)
VRBO
A paradise of cypress and olive trees
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Close to cycling, hiking trails, and more, this smoke-free vacation home brings it all within reach. Jump into your c ...
From $266 per night (USD)VRBO
- From $156 per night (USD)
VRBO
Belvilla by OYO Farmhouse in Radda with Garden
- Bedrooms:
- 6
- Bathrooms:
- 2
- Sleeps:
- 6
This 2-bedroom farmhouse in Radda In Chianti is ideal for a small family with kids. Located in Tuscany, Italy, it can ho ...
From $156 per night (USD)VRBO
- From $134 per night (USD)
Expedia
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
<p>You'll find bicycles on site at this pet-friendly vacation home. Jump into your car and make short work of the 25-min ...
From $134 per night (USD)Expedia
- From $170 per night (USD)
VRBO
Federico farmhouse with swimming pool and jacuzzi, panoramic position in Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>You'll find bicycles on site at this pet-friendly vacation home. Jump into your car and make short work of the 25-min ...
From $170 per night (USD)VRBO
- From $129 per night (USD)
Expedia
Farmhouse with beautiful pool and jacuzzi, panoramic location in chianti
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 16
<p>You'll find bicycles on site at this pet-friendly vacation home. Jump into your car and make short work of the 25-min ...
From $129 per night (USD)Expedia
- From $2035 per night (USD)
VRBO
Villa \"Cottage San Bartolomeo\" with Mountain View, Pool & Wi-Fi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
The San Bartolomeo Cottage impresses guests with its fantastic view of the hills and valley. The 100 m² cottage consists ...
From $2035 per night (USD)VRBO
- From $562 per night (USD)
Expedia
Belvilla by OYO Villa Ulivo
- Bedrooms:
- 12
- Bathrooms:
- 6
- Sleeps:
- 16
Resting in Radda In Chianti, Tuscany, Italy, this 7-bedroom farmhouse can host a family or group of 14. Just 2 km from t ...
From $562 per night (USD)Expedia
- From $5435 per night (USD)
VRBO
Chianti villa rental
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Villa Castiglioni is a stunning Chianti villa rental. It is situated in the Chianti region in Tuscany, an area ...
From $5435 per night (USD)VRBO
- From $1036 per night (USD)
Expedia
Villa Al Bosco: An elegant and welcoming three-story villa situated in a secluded location surrounded by meadows and by green hills, with Free WI-FI.
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Villa Al Bosco is an elegant and welcoming three-story villa situated in a secluded location surrounded by meadows and b ...
From $1036 per night (USD)Expedia
- From $1013 per night (USD)
VRBO
Villa Al Borgo: A welcoming two-story villa located in a characteristic village, with Free WI-FI.
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 11
Villa Al Borgo is a welcoming two-story villa located in a characteristic village. It sleeps 11 people. From Villa Al Bo ...
From $1013 per night (USD)VRBO
- From $747 per night (USD)
Expedia
Casa Perano, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Imagine the perfect Chianti villa – a secluded house with private pool and fabulous 180-degree views starring a hilltop ...
From $747 per night (USD)Expedia
- From $899 per night (USD)
VRBO
Charming Stone Villa with Pool in the heart of the Chianti countryside in Siena.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
A fascinating renewed stone farmhouse with a stunning private pool and stylish external dining and seating area in the h ...
From $899 per night (USD)VRBO
- From $4370 per night (USD)
VRBO
Luxury Tuscany villa
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Villa Vecchio is a super-stylish luxury Tuscany villa on a wine estate in the heart Chianti region. Originally ...
From $4370 per night (USD)VRBO
- From $635 per night (USD)
VRBO
Cielo di Radda, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A smart villa with a private pool just a short walk from one of Tuscany’s honeypot historic towns – what more could you ...
From $635 per night (USD)VRBO
- From $1817 per night (USD)
Expedia
Private villa in Chianti with swimming pool surrounded by nature
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 24
<p>Close to ecotours, winery tours, and more, this pet-friendly villa brings it all within reach. Thanks to the convenie ...
From $1817 per night (USD)Expedia
- From $468 per night (USD)
VRBO
Casa Momi - One Bedroom Villa, Sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This romantic home in the Chianti Classico countryside offers stunning views of rolling hills, forests, and vineyards an ...
From $468 per night (USD)VRBO
- From $210 per night (USD)
Expedia
Cottage \"Podere in Volpaia\" with Garden & Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Located in Radda in Chianti, the cottage "Podere in Volpaia" has everything you need for a comfortable holiday. The 85 m ...
From $210 per night (USD)Expedia
- From $158 per night (USD)
VRBO
Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The traditional holiday apartment 'Rifugio sulla via di Volpaia' is located in Radda in Chianti and is the ideal accommo ...
From $158 per night (USD)VRBO
- From $752 per night (USD)
VRBO
PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
The Piaggione of Serravalle, at a glance, appears as a gem naturally cast on the highest ridges of the Chianti hills of ...
From $752 per night (USD)VRBO
- From $745 per night (USD)
VRBO
Casa Boccaccio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Immerse yourself in the beautiful Chianti countryside at this semi-detached apartment set in a cluster of 10 private sto ...
From $745 per night (USD)VRBO
- From $160 per night (USD)
Expedia
Wonderful private villa with A\/C, WIFI, TV, terrace, pets allowed, panoramic view and parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Property Summary Welcome to "Casa Chiara," a modern two-story vacation rental built in 2009 and conveniently located jus ...
From $160 per night (USD)Expedia
- From $511 per night (USD)
VRBO
Beautiful private villa for 14 guests with private pool, WIFI, TV, terrace, pets allowed and par...
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Property Summary The Le Bonatte farm offers a cozy and simple vacation rental situated in the heart of the Chianti Class ...
From $511 per night (USD)VRBO
- From $228 per night (USD)
Expedia
Casa Marina, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Immerse yourself in Tuscan daily life at Casa Marina, a townhouse on a pretty street in the heart of Radda. Take up resi ...
From $228 per night (USD)Expedia
- From $2619 per night (USD)
VRBO
Borgo Merlo - Nine Bedroom Villa, Sleeps 22
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 22
You will find Borgo Merlo in the verdant Chianti hills in the heart of Tuscany. The accommodation here comprises three n ...
From $2619 per night (USD)VRBO
- From $170 per night (USD)
Expedia
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $170 per night (USD)Expedia