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Radda in Chianti Rentals

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Results: 100 Rentals

  • Casale il Gualdo In Radda in Chianti, Tuscany
    From $847 per night (USD)

    VRBO

    Casale il Gualdo In Radda in Chianti, Tuscany

    Bedrooms:
    6
    Bathrooms:
    8
    Sleeps:
    16

    Property for exclusive use Casale il Gualdo is an old stone house, completely independent, measuring 300 sq. m. and capa ...

    From $847 per night (USD)

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    Details
  • Il Corno, Radda in Chianti, Siena and Chianti
    From $693 per night (USD)

    Expedia

    Il Corno, Radda in Chianti, Siena and Chianti

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    8

    Il Corno is a beautifully restored farmhouse in a stunning panoramic position, ideal for a large family or a group of fr ...

    From $693 per night (USD)

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    Details
  • Il Torrino In Radda in Chianti, Tuscany
    From $741 per night (USD)

    VRBO

    Il Torrino In Radda in Chianti, Tuscany

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    Property for exclusive use Il Torrino is a beautiful country home, composed of a main house and an annex, sleeping 12 in ...

    From $741 per night (USD)

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    Details
  • Stunning private villa for 12 guests with A/C, private pool, WIFI, close to Greve In Chianti
    From $3150 per night (USD)

    Expedia

    Stunning private villa for 12 guests with A/C, private pool, WIFI, close to Greve In Chianti

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    12

    Villa Pianvecchio is a beautiful holiday home with WiFi internet, private pool and air conditioning. The property can ...

    From $3150 per night (USD)

    Expedia

    Details
  •  Villa San Piero in Chianti - First Class Service, Top Location, Maximum Privacy
    From $1830 per night (USD)

    VRBO

    Villa San Piero in Chianti - First Class Service, Top Location, Maximum Privacy

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    YOUR VACATION DREAM BECOMES REALITY. Fully restored luxury Villa with 700 years of history, romantic chapel and antiq ...

    From $1830 per night (USD)

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  • Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)
    From $446 per night (USD)

    Expedia

    Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    12

    ---------- IMPORTANT: WE HAVE RECENTLY ADDED THIS PROPERTY TO OUR WALLET. LOOK AT OUR FEEDBACKS FOR THE OTHER PROPERTIES ...

    From $446 per night (USD)

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  • Molino del Ponte, Radda in Chianti, Italy
    From $300 per night (USD)

    VRBO

    Molino del Ponte, Radda in Chianti, Italy

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    If you have ever wondered what was life like in the Tuscan region of Italy in the 1600s, look no further than this retre ...

    From $300 per night (USD)

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  • L'Angolino In Radda in Chianti, Tuscany
    From $322 per night (USD)

    VRBO

    L'Angolino In Radda in Chianti, Tuscany

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    ***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Property for exclusive use Be ...

    From $322 per night (USD)

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  • La Terrazza by Interhome
    From $234 per night (USD)

    VRBO

    La Terrazza by Interhome

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    La Terrazza is a typical manor house, located in the heart of the Chianti Classico area, which preserves the atmosphere ...

    From $234 per night (USD)

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  • Private Villa with private pool, WIFI, hot tub, TV, patio, panoramic view, close to Greve In Chianti
    From $1032 per night (USD)

    Expedia

    Private Villa with private pool, WIFI, hot tub, TV, patio, panoramic view, close to Greve In Chianti

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    10

    Camporempoli is a lovely stone building (400 sq m) with private pool and WiFi internet. The property can sleep up to te ...

    From $1032 per night (USD)

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    Details
  • Private Villa with private pool, WIFI, TV, terrace, panoramic view, close to Greve In Chianti
    From $846 per night (USD)

    VRBO

    Private Villa with private pool, WIFI, TV, terrace, panoramic view, close to Greve In Chianti

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    12

    Conveniently located 3 km (2 mi) from Volpaia, Italy in the tourist area "Chianti" and only 21 km (13 mi) from Greve In ...

    From $846 per night (USD)

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    Details
  • Private Villa with private pool, WIFI, TV, terrace, panoramic view, close to Greve In Chianti
    From $846 per night (USD)

    Expedia

    Private Villa with private pool, WIFI, TV, terrace, panoramic view, close to Greve In Chianti

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    11

    Conveniently located in the centre of Volpaia, Italy in the tourist area "Chianti" and only 23 km (14 mi) from Greve In ...

    From $846 per night (USD)

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    Details
  • Docciole: Chianti Villa and Pool for 12
    From $562 per night (USD)

    VRBO

    Docciole: Chianti Villa and Pool for 12

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    12

    Docciole is a wonderful family villa, once a Tuscan farmhouse, converted and designed for family reunions - it provides ...

    From $562 per night (USD)

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  • Il Cipresso, Radda in Chianti, Siena and Chianti
    From $187 per night (USD)

    Expedia

    Il Cipresso, Radda in Chianti, Siena and Chianti

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Il Cipresso is a lovingly furnished holiday home, ideal for a couple or a small family. It is located on the ground floo ...

    From $187 per night (USD)

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    Details
  • Stunning  villa for 6 people with WIFI, TV, terrace, pets allowed and panoramic view
    From $259 per night (USD)

    VRBO

    Stunning villa for 6 people with WIFI, TV, terrace, pets allowed and panoramic view

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Property Summary Nestled in the heart of the Chianti Classico region in Radda in Chianti, Italy, La Terrazza is a charm ...

    From $259 per night (USD)

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  • Marangole 12, Emma Villas
    From $3029 per night (USD)

    Expedia

    Marangole 12, Emma Villas

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    12

    The Price includes: -Utilities: electricity - water - gas for cooking use - weekly linen, initial and final cleaning - ...

    From $3029 per night (USD)

    Expedia

    Details
  •  In the heart of Chianti: view over the valley, relaxation & art, wine & sun
    From $158 per night (USD)

    VRBO

    In the heart of Chianti: view over the valley, relaxation & art, wine & sun

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Val delle Corti is a small winery in Radda in Chianti. The ‘Capanna’, an old, tastefully restored natural stone hay bar ...

    From $158 per night (USD)

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  • Villa La Poiana 10, Emma Villas
    From $1175 per night (USD)

    Expedia

    Villa La Poiana 10, Emma Villas

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    The Price includes: - Utilities: electricity - water - gas for cooking use - weekly linen, initial and final cleaning - ...

    From $1175 per night (USD)

    Expedia

    Details
  • Private Villa with A/C, hot tub, sauna, WIFI, private pool, TV, patio, close to Greve In Chianti
    From $3229 per night (USD)

    VRBO

    Private Villa with A/C, hot tub, sauna, WIFI, private pool, TV, patio, close to Greve In Chianti

    Bedrooms:
    7
    Bathrooms:
    5
    Sleeps:
    11

    Conveniently located 4 km (2 mi) from Radda In Chianti, Italy in the tourist area "Siena And Surroundings" and only 23 k ...

    From $3229 per night (USD)

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  • Villa in Volpaia with 4 bedrooms sleeps 8
    From $587 per night (USD)

    Expedia

    Villa in Volpaia with 4 bedrooms sleeps 8

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    This beautiful farmhouse with private pool is located in a very quiet and secluded position in a panoramic position of C ...

    From $587 per night (USD)

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    Details
  • Fiorita In Radda in Chianti, Tuscany
    From $457 per night (USD)

    VRBO

    Fiorita In Radda in Chianti, Tuscany

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    ***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL*** Property for exclusive use Ty ...

    From $457 per night (USD)

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    Details
  • Villa in Lucarelli with 6 bedrooms sleeps 10
    From $658 per night (USD)

    Expedia

    Villa in Lucarelli with 6 bedrooms sleeps 10

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    10

    This exquisitely restored farmhouse is situated in one of the most beautiful positions, right in the heart of Chianti ...

    From $658 per night (USD)

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    Details
  • Villa in Volpaia with 6 bedrooms sleeps 12
    From $738 per night (USD)

    VRBO

    Villa in Volpaia with 6 bedrooms sleeps 12

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    12

    This beautiful farmhouse with private pool is located in a very quiet and secluded position in a panoramic position of C ...

    From $738 per night (USD)

    VRBO

    Details
  • Crognole 6, Emma Villas
    From $1220 per night (USD)

    Expedia

    Crognole 6, Emma Villas

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    The Price includes: - Utilities: electricity, water, gas for kitchen use - weekly linen, initial and final cleaning - Z ...

    From $1220 per night (USD)

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    Details
  • Il Poggetto a Vescinino, Radda in Chianti, Siena and Chianti
    From $267 per night (USD)

    VRBO

    Il Poggetto a Vescinino, Radda in Chianti, Siena and Chianti

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Il Poggetto a Vescinino is a welcoming holiday home in the heart of Chianti, ideal for a family holiday. Set on a peacef ...

    From $267 per night (USD)

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  • La Casa di Radda, Radda in Chianti, Siena and Chianti
    From $432 per night (USD)

    Expedia

    La Casa di Radda, Radda in Chianti, Siena and Chianti

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    La Casa di Radda is a welcoming holiday home in the Chianti Classico region, notable for its proximity to the charming v ...

    From $432 per night (USD)

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    Details
  • Casino di Vescine, Radda in Chianti, Siena and Chianti
    From $525 per night (USD)

    VRBO

    Casino di Vescine, Radda in Chianti, Siena and Chianti

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Casino di Vescine is a charming Chianti country house in a peaceful, private setting surrounded by olive groves and the ...

    From $525 per night (USD)

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  • Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
    From $804 per night (USD)

    Expedia

    Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Tenuta lo Spugno is a luxurious holiday villa in Chianti, set in a secluded position on the side of a hill with breathta ...

    From $804 per night (USD)

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    Details
  • Vivaio, Radda in Chianti, Siena and Chianti
    From $952 per night (USD)

    VRBO

    Vivaio, Radda in Chianti, Siena and Chianti

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    Vivaio is a spacious holiday home in the heart of Chianti Classico, surrounded by a beautifully landscaped garden with l ...

    From $952 per night (USD)

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  • Uva, Ceperano, Radda in Chianti, Siena and Chianti
    From $171 per night (USD)

    Expedia

    Uva, Ceperano, Radda in Chianti, Siena and Chianti

    Bedrooms:
    1
    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 $171 per night (USD)

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    Details
  • Il Casetto, Radda in Chianti, Siena and Chianti
    From $811 per night (USD)

    VRBO

    Il Casetto, Radda in Chianti, Siena and Chianti

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Il Casetto is a luxurious holiday home set in a peaceful countryside location, surrounded by vineyards and rolling hills ...

    From $811 per night (USD)

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  • La Casanova, Radda in Chianti, Siena and Chianti
    From $195 per night (USD)

    Expedia

    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 $195 per night (USD)

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  • Il Boschetto, Radda in Chianti, Siena and Chianti
    From $344 per night (USD)

    VRBO

    Il Boschetto, Radda in Chianti, Siena and Chianti

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Il Boschetto is a charming Chianti holiday home with beautiful views over olive groves, vineyards and the rolling Tuscan ...

    From $344 per night (USD)

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  • Ulivo, Ceperano, Radda in Chianti, Siena and Chianti
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    Expedia

    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 ...

    Click For Pricing

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    Details
  • Girasole, Ceperano, Radda in Chianti, Siena and Chianti
    From $157 per night (USD)

    VRBO

    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 $157 per night (USD)

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  • Angolino, Radda in Chianti, Siena and Chianti
    From $316 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 $316 per night (USD)

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  • Limoni, Ceperano, Radda in Chianti, Siena and Chianti
    From $182 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 $182 per night (USD)

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  • Casa di Pesa, Radda in Chianti, Siena and Chianti
    From $265 per night (USD)

    Expedia

    Casa di Pesa, Radda in Chianti, Siena and Chianti

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Casa di Pesa is a charming Chianti holiday home with a well-kept garden, a beautiful pool, and traditional Tuscan charac ...

    From $265 per night (USD)

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    Details
  • Calafralina, Radda in Chianti, Siena and Chianti
    From $715 per night (USD)

    VRBO

    Calafralina, Radda in Chianti, Siena and Chianti

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Calafralina is a spacious Chianti holiday home, ideal for several couples or a group of friends travelling together whil ...

    From $715 per night (USD)

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    Details
  • Poggio della Villa, Radda in Chianti, Siena and Chianti
    From $417 per night (USD)

    Expedia

    Poggio della Villa, Radda in Chianti, Siena and Chianti

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Poggio della Villa is a beautiful Chianti holiday home just two kilometres from the centre of Radda, offering everything ...

    From $417 per night (USD)

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  • Ancient stone farmhouse on a top of Chianti Hill with private garden and lake
    From $191 per night (USD)

    VRBO

    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 $191 per night (USD)

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    Details
  • Stone Farmhouse in Chianti Hill between Florence, Siena private veranda and lake
    From $232 per night (USD)

    Expedia

    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 $232 per night (USD)

    Expedia

    Details
  • Farmhouse 15th century in Chianti with garden between Florence and Siena
    From $193 per night (USD)

    VRBO

    Farmhouse 15th century in Chianti with garden between Florence and Siena

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets ...

    From $193 per night (USD)

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    Details
  • Ancient house in Chianti Hills with private lake and garden
    From $192 per night (USD)

    Expedia

    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 $192 per night (USD)

    Expedia

    Details
  • Le Bonatte by Interhome
    From $163 per night (USD)

    VRBO

    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 $163 per night (USD)

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  • Le Bonatte by Interhome
    From $303 per night (USD)

    Expedia

    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 $303 per night (USD)

    Expedia

    Details
  • Beautiful private villa with WIFI, private pool, A/C, TV, patio, pets allowed and panoramic view
    From $327 per night (USD)

    VRBO

    Beautiful private villa with WIFI, private pool, A/C, TV, patio, pets allowed and panoramic view

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Property Summary Nestled in the serene Tuscan countryside just 2 km from the charming village of Radda in Chianti, Ital ...

    From $327 per night (USD)

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    Details
  • Le Bonatte by Interhome
    From $495 per night (USD)

    Expedia

    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 $495 per night (USD)

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    Details
  • Villa Radda - Florence Area
    From $4196 per night (USD)

    VRBO

    Villa Radda - Florence Area

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    11

    VILLA RADDA - FLORENCE AREA With its beautiful medieval tower set up as a wine bar, the villa offers spectacular views a ...

    From $4196 per night (USD)

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  • Villa Pianvecchio by Fantasia Villas
    From $3576 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 $3576 per night (USD)

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    Details
  • Villa Montemaggio by Fantasia Villas
    From $1369 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 $1369 per night (USD)

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  • Villa Castiglioni by Fantasia Villas
    From $4710 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 $4710 per night (USD)

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  • Escape to Vineyards, Elba
    From $163 per night (USD)

    VRBO

    Escape to Vineyards, Elba

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This 2-bedroom farmhouse situated in Radda in Chianti is suitable for a small group or family. Resting in Tuscany, Italy ...

    From $163 per night (USD)

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  • Luxury Villa in Tuscany for 10 People
    From $3646 per night (USD)

    Expedia

    Luxury Villa in Tuscany for 10 People

    Bedrooms:
    7
    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 $3646 per night (USD)

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  • Pretty farmhouse with terrace
    From $165 per night (USD)

    VRBO

    Pretty farmhouse with terrace

    Bedrooms:
    4
    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 $165 per night (USD)

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    Details
  • Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
    From $1543 per night (USD)

    Expedia

    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 $1543 per night (USD)

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  • Case Domine, Radda in Chianti, Siena and Chianti
    From $576 per night (USD)

    VRBO

    Case Domine, Radda in Chianti, Siena and Chianti

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Case Domine is a lovingly restored Tuscan holiday home nestled among the vineyards of the  Chianti Classico. The buildin ...

    From $576 per night (USD)

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  • Apartment in Radda with Garden
    From $154 per night (USD)

    Expedia

    Apartment in Radda with Garden

    Bedrooms:
    4
    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 $154 per night (USD)

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    Details
  • Chianti Hillside Farmhouse
    From $584 per night (USD)

    VRBO

    Chianti Hillside Farmhouse

    Bedrooms:
    9
    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 $584 per night (USD)

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  • 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.
    From $1526 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:
    6
    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 $1526 per night (USD)

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    Details
  • Cielo di Radda, Radda in Chianti, Siena and Chianti
    From $412 per night (USD)

    VRBO

    Cielo di Radda, Radda in Chianti, Siena and Chianti

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Cielo di Radda is a stylish villa in the heart of the Chianti Classico, just a few minutes’ walk from the charming town ...

    From $412 per night (USD)

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  • Cottage \Podere in Volpaia\ with Garden & Wi-Fi
    From $316 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 $316 per night (USD)

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    Details
  • Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning
    From $467 per night (USD)

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    Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The traditional holiday apartment 'Rifugio sulla via di Volpaia' is located in Radda in Chianti and is the ideal accommo ...

    From $467 per night (USD)

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    Details
  • Beautiful private villa for 14 guests with WIFI, private pool, TV, terrace and pets allowed
    From $549 per night (USD)

    Expedia

    Beautiful private villa for 14 guests with WIFI, private pool, TV, terrace and pets allowed

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    14

    Property Summary Nestled in the heart of the renowned Chianti Classico region of Italy, Le Bonatte is a charming and ch ...

    From $549 per night (USD)

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    Details
  • Casa Marina, Radda in Chianti, Siena and Chianti
    From $233 per night (USD)

    VRBO

    Casa Marina, Radda in Chianti, Siena and Chianti

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Casa Marina is a charming three-storey holiday home located in the historic center of Radda, one of the most beautiful t ...

    From $233 per night (USD)

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  • Fico del Corno, Radda in Chianti, Siena and Chianti
    From $330 per night (USD)

    Expedia

    Fico del Corno, Radda in Chianti, Siena and Chianti

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Fico del Corno is a charming stone villa in the heart of the Chianti Classico, ideal for couples or a small family looki ...

    From $330 per night (USD)

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    Details
  • Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
    From $1119 per night (USD)

    VRBO

    Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    11

    The villa La Petrosa is located in Radda in Chianti and is the ideal accommodation for a relaxing getaway. The 3-storey ...

    From $1119 per night (USD)

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  • Fienile al Corno, Radda in Chianti, Siena and Chianti
    From $343 per night (USD)

    Expedia

    Fienile al Corno, Radda in Chianti, Siena and Chianti

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Fienile al Corno is a charming holiday home in the Chianti Classico, ideal for a relaxing break with family or friends. ...

    From $343 per night (USD)

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    Details
  • Casale Al Sole Tra Le Vecchie Vigne, Radda in Chianti, Radda in Chianti, Italy
    From $380 per night (USD)

    VRBO

    Casale Al Sole Tra Le Vecchie Vigne, Radda in Chianti, Radda in Chianti, Italy

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Live the Tuscan dream in this stunningly renovated 17th-century farmhouse, in the heart of the Chianti hills! Casale al ...

    From $380 per night (USD)

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    Details
  • Villa Tower House Fattoria di Montemaggio
    From $1691 per night (USD)

    VRBO

    Villa Tower House Fattoria di Montemaggio

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    <p>Located in Radda in Chianti, this 3-bedroom, 3-bathroom villa lets you experience it all. Fans of nature and the outd ...

    From $1691 per night (USD)

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  • Villa in Radda In Chianti with 6 bedrooms sleeps 12
    From $2492 per night (USD)

    VRBO

    Villa in Radda In Chianti with 6 bedrooms sleeps 12

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    Villa Pianoro is a charming, panoramic villa in the rolling hills of Radda in Chianti which looks out over vineyards and ...

    From $2492 per night (USD)

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  • La Capanna - Radda in Chianti. Newly renovated  stone farmhouse with pool & A/C
    From $681 per night (USD)

    Expedia

    La Capanna - Radda in Chianti. Newly renovated stone farmhouse with pool & A/C

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to La Capanna @ Casa Volpino. A Tuscan farmhouse in the heart of the Chianti Region. Built over the old animal s ...

    From $681 per night (USD)

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    Details
  • Villa Poggio la Croce by MMega
    From $841 per night (USD)

    VRBO

    Villa Poggio la Croce by MMega

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    External Description Villa Poggio la Croce is located in the wonderful Chianti countryside, just 2 km from Radda in C ...

    From $841 per night (USD)

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  • Villa del Poggio by Interhome
    From $295 per night (USD)

    Expedia

    Villa del Poggio by Interhome

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Very beautiful, cosy, rustic single-family house "Villa del Poggio", surrounded by trees and vineyards. 2 km from the ce ...

    From $295 per night (USD)

    Expedia

    Details
  • Chianti dreaming in Radda
    From $395 per night (USD)

    VRBO

    Chianti dreaming in Radda

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    <p>Located in a village, this welcoming apartment lets you experience it all in Radda in Chianti. With convenient onsite ...

    From $395 per night (USD)

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  • Home 'Serena, Radda In Chianti' with Private Pool, Private Terrace and Wi-Fi
    From $259 per night (USD)

    Expedia

    Home 'Serena, Radda In Chianti' with Private Pool, Private Terrace and Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Located in Radda in Chianti, the holiday home Casa Serena, Radda In Chianti has everything you need for a relaxing holid ...

    From $259 per night (USD)

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    Details
  • Villa il pozzo della volpe
    From $636 per night (USD)

    VRBO

    Villa il pozzo della volpe

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    11

    Nestled in the heart of the picturesque Greve in Chianti, this family-friendly villa offers a tranquil oasis for your ne ...

    From $636 per night (USD)

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    Details
  • Villa Radda - Florence Area
    From $3591 per night (USD)

    Expedia

    Villa Radda - Florence Area

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    9

    VILLA RADDA - FLORENCE AREA With its beautiful medieval tower set up as a wine bar, the villa offers spectacular views a ...

    From $3591 per night (USD)

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  • Charming Villa W/ Private Pool in Heart of Chianti
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    VRBO

    Charming Villa W/ Private Pool in Heart of Chianti

    Bedrooms:
    4
    Bathrooms:
    8
    Sleeps:
    8

    <p>Located in Radda in Chianti, this 8-bedroom, 4-bathroom villa lets you experience it all. Fans of nature and the outd ...

    Click For Pricing

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  • Villa Piandolce - Radda In Chianti
    From $4196 per night (USD)

    Expedia

    Villa Piandolce - Radda In Chianti

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    VILLA PIANDOLCE - RADDA IN CHIANTI - SIENA AREA The property offers all modern technology and comforts. In the immediate ...

    From $4196 per night (USD)

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    Details
  • Villa Piandolce - Radda In Chianti
    From $4139 per night (USD)

    VRBO

    Villa Piandolce - Radda In Chianti

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    VILLA PIANDOLCE - RADDA IN CHIANTI - SIENA AREA The property offers all modern technology and comforts. In the immediate ...

    From $4139 per night (USD)

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  • Stunning villa with large pool in the heart of Chianti 12km from Siena
    From $1122 per night (USD)

    Expedia

    Stunning villa with large pool in the heart of Chianti 12km from Siena

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Discover the timeless charm of Tuscany in this marvelous traditional stone Villa nestled in the heart of picturesque Chi ...

    From $1122 per night (USD)

    Expedia

    Details
  • My Rental Homes - Villa Torre del Chianti with hited pool, Gym and wellness center
    From $4810 per night (USD)

    VRBO

    My Rental Homes - Villa Torre del Chianti with hited pool, Gym and wellness center

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Villa Torre del Chianti is a unique property in the heart of the Chianti reagion in Tuscany, a step away from Radda in C ...

    From $4810 per night (USD)

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  • Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV
    From $322 per night (USD)

    Expedia

    Chianti dreaming in Radda-3 independent bedrooms with private bathroom and TV

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This apartment located on the outskirts of Radda in Chianti is the ideal choice for those looking for an elegant and com ...

    From $322 per night (USD)

    Expedia

    Details
  • La Pesa di Mezzo, Radda in Chianti, Siena and Chianti
    From $412 per night (USD)

    VRBO

    La Pesa di Mezzo, Radda in Chianti, Siena and Chianti

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    La Pesa di Mezzo is a beautifully restored Tuscan barn set in the heart of the unspoilt Chianti countryside.The property ...

    From $412 per night (USD)

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  • Campo Agli Olivi, Radda in Chianti, Siena and Chianti
    From $317 per night (USD)

    Expedia

    Campo Agli Olivi, Radda in Chianti, Siena and Chianti

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    4

    Campo Agli Olivi is a charming Tuscan stone villa nestled in the gentle hills of the Chianti region, offering two indepe ...

    From $317 per night (USD)

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    Details
  • Panoramic Chianti Villa with Private Pool & SPA - Castellare Petroso
    From $957 per night (USD)

    VRBO

    Panoramic Chianti Villa with Private Pool & SPA - Castellare Petroso

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to Castellare Petroso, where the Tuscan dream comes to life. This magnificent villa is located in the heart of C ...

    From $957 per night (USD)

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    Details
  • Muricciaglia 14, Emma Villas
    From $3044 per night (USD)

    Expedia

    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 $3044 per night (USD)

    Expedia

    Details
  • Casa dell'Uva by Interhome
    From $248 per night (USD)

    VRBO

    Casa dell'Uva by Interhome

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Terraced house, built in 2012. 300 m from the centre of Radda in Chianti, 11 km from the centre of Gaiole in Chianti, 57 ...

    From $248 per night (USD)

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    Details
  • Stunning  villa for 4 people with WIFI and TV
    From $275 per night (USD)

    Expedia

    Stunning villa for 4 people with WIFI and TV

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Property Summary Nestled in the heart of Tuscany, this charming terraced house offers an exceptional holiday rental exp ...

    From $275 per night (USD)

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    Details
  • Dream House in Tuscany, with Amazing View and Pool
    From $706 per night (USD)

    VRBO

    Dream House in Tuscany, with Amazing View and Pool

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    Perched on a hill in the heart of Chianti, our family home offers breathtaking panoramic views across the rolling hills ...

    From $706 per night (USD)

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    Details
  • Beautiful apartment for 5 guests with WIFI, A/C, TV and patio
    From $204 per night (USD)

    Expedia

    Beautiful apartment for 5 guests with WIFI, A/C, TV and patio

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Property Summary Nestled in the serene Tuscan countryside of Castellina in Chianti, Italy, the charming apartment house ...

    From $204 per night (USD)

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    Details
  • Fiore di Mandorlo by Interhome
    From $179 per night (USD)

    VRBO

    Fiore di Mandorlo by Interhome

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Castellina in Chianti: Old, historical apartment house "Fiore di Mandorlo", renovated. 4 km from the centre of Castellin ...

    From $179 per night (USD)

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  • Timeless stillness, steps from the piazza
    From $2336 per night (USD)

    VRBO

    Timeless stillness, steps from the piazza

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    Radda in Chianti is one of the last true medieval villages of the Chianti Classico. In a region where luxury villas sit ...

    From $2336 per night (USD)

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  • Tuscany Country House in Central Chianti Wine Country, Amazing Panoramic Views
    From $366 per night (USD)

    VRBO

    Tuscany Country House in Central Chianti Wine Country, Amazing Panoramic Views

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Tour (no spaces) www. escapetochianti. com/experience The location is fantastic and a perfect central base in Tuscany! ...

    From $366 per night (USD)

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  • Villa Eterna, Tuscan Haven in the Heart of Chianti
    From $2634 per night (USD)

    Expedia

    Villa Eterna, Tuscan Haven in the Heart of Chianti

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    VILLA ETERNA - RADDA IN CHIANTI Only a five-minute walk from Radda in Chianti, the villa is set just outside the charmin ...

    From $2634 per night (USD)

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    Details
  • Private Pool Retreat in Chianti
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    Private Pool Retreat in Chianti

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Casa Momi is a charming retreat set in the Chianti Classico countryside, offering views across rolling hills, forests an ...

    Click For Pricing

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    Details
  • Chianti Retreat with Heated Pool, Spa and Panoramic Views
    Click For Pricing

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    Chianti Retreat with Heated Pool, Spa and Panoramic Views

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This three-bedroom farmhouse is a lovingly restored Tuscan retreat set in the hills around Radda in Chianti, offering so ...

    Click For Pricing

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    Details
  • Chianti country retreat 4 pax
    From $337 per night (USD)

    VRBO

    Chianti country retreat 4 pax

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to our historic stone farmhouse, nestled in the peaceful Chianti Classico hills. Located just a few minutes from ...

    From $337 per night (USD)

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    Details
  • Chianti country retreat 6 pax
    From $492 per night (USD)

    Expedia

    Chianti country retreat 6 pax

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our historic stone farmhouse, nestled in the peaceful hills of Chianti Classico. Located just a few minutes f ...

    From $492 per night (USD)

    Expedia

    Details