Search Your Destination Now!

Radda in Chianti Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Update Results Reset Dates
Filter

Results: 287 Rentals

  • Casa Lucomeni, Radda in Chianti, Siena and Chianti
    From $666 per night (USD)

    VRBO

    Casa Lucomeni, Radda in Chianti, Siena and Chianti

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    9

    There’s a real sense of luxury about this two-storey villa, even in the outside spaces. The private pool has an infinity ...

    From $666 per night (USD)

    VRBO

    Details
  • Il Corno, Radda in Chianti, Siena and Chianti
    From $450 per night (USD)

    Expedia

    Il Corno, Radda in Chianti, Siena and Chianti

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    8

    A magnificently positioned restored farmhouse, situated on its own rise in the heart of the Chianti area, Il Corno effor ...

    From $450 per night (USD)

    Expedia

    Details
  • Stunning private villa with A\/C, WIFI, private pool and parking, close to Greve In Chianti
    From $4014 per night (USD)

    VRBO

    Stunning private villa with A\/C, WIFI, private pool and parking, close to Greve In Chianti

    Bedrooms:
    8
    Bathrooms:
    6
    Sleeps:
    12

    Conveniently located 2 km (1 mi) from Radda In Chianti, Italy in the tourist area "Siena And Surroundings" and only 22 k ...

    From $4014 per night (USD)

    VRBO

    Details
  • Gorgeous villa with new pool in the heart of Chianti (wi fi and whirlpool)
    From $438 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 $438 per night (USD)

    Expedia

    Details
  • APARTMENT IN THE HEART OF CHIANTI; BOOK DIRECTLY TO THE OWNER
    From $238 per night (USD)

    VRBO

    APARTMENT IN THE HEART OF CHIANTI; BOOK DIRECTLY TO THE OWNER

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    The apartment, with the classic structure of local houses with exposed beams, is independent and located on the ground f ...

    From $238 per night (USD)

    VRBO

    Details
  • Colto Dei Pallanti - Three Bedroom Villa, Sleeps 6
    From $813 per night (USD)

    Expedia

    Colto Dei Pallanti - Three Bedroom Villa, Sleeps 6

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Radda, Chianti. Surrounded by beautiful hills, the villa is ideally situated for exploring Italy’s cultural treasures as ...

    From $813 per night (USD)

    Expedia

    Details
  • La Terrazza by Interhome
    From $222 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 $222 per night (USD)

    VRBO

    Details
  • Private Villa with hot tub, private pool, WIFI, TV, patio, panoramic view, close to Greve In Chianti
    From $929 per night (USD)

    Expedia

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

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    10

    Conveniently located 3 km (2 mi) from Lucarelli, Italy in the tourist area "Chianti" and only 16 km (10 mi) from Greve I ...

    From $929 per night (USD)

    Expedia

    Details
  • Il Cipresso, Radda in Chianti, Siena and Chianti
    From $172 per night (USD)

    VRBO

    Il Cipresso, Radda in Chianti, Siena and Chianti

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Il Cipresso is tucked into a hillside hamlet in the green heart of the Chianti on the halfway mark between idyllic Caste ...

    From $172 per night (USD)

    VRBO

    Details
  • Villa Casa al Sole Large Private Pool, WiFi
    From $428 per night (USD)

    Expedia

    Villa Casa al Sole Large Private Pool, WiFi

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Overview Villa Casa al Sole is located in Florence, Tuscany. This detached vacation rental property offers Free Wi ...

    From $428 per night (USD)

    Expedia

    Details
  • Private Villa with private pool, WIFI, TV, terrace, panoramic view, close to Greve In Chianti
    From $855 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

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

    From $855 per night (USD)

    VRBO

    Details
  • Private Villa with WIFI, private pool, TV, terrace, panoramic view, close to Greve In Chianti
    From $1113 per night (USD)

    Expedia

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

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    11

    Pozza Di Volpaia is a nice stone building (300 sq m) with private pool and WiFi internet. The property can accommodate ...

    From $1113 per night (USD)

    Expedia

    Details
  • Stunning  villa for 6 people with WIFI, TV, terrace, pets allowed, panoramic view and parking
    From $254 per night (USD)

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Property Summary La Terrazza is a charming manor house in the heart of Chianti Classico region, offering an authentic ex ...

    From $254 per night (USD)

    VRBO

    Details
  • Marangole 12, Emma Villas
    From $1684 per night (USD)

    Expedia

    Marangole 12, Emma Villas

    Bedrooms:
    8
    Bathrooms:
    7
    Sleeps:
    12

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

    From $1684 per night (USD)

    Expedia

    Details
  •  In the heart of Chianti: view over the valley, relaxation & art, wine & sun
    From $151 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 $151 per night (USD)

    VRBO

    Details
  • Villa La Poiana 10, Emma Villas
    From $1240 per night (USD)

    Expedia

    Villa La Poiana 10, Emma Villas

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    10

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

    From $1240 per night (USD)

    Expedia

    Details
  • Private Villa with sauna, private pool, A\/C, hot tub, WIFI, TV, patio, close to Greve In Chianti
    From $4016 per night (USD)

    VRBO

    Private Villa with sauna, private pool, A\/C, hot tub, WIFI, 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 $4016 per night (USD)

    VRBO

    Details
  • Radda in Chianti  5 bedroom luxury  villa rental, heated pool, wine estate
    From $3385 per night (USD)

    Expedia

    Radda in Chianti 5 bedroom luxury villa rental, heated pool, wine estate

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    Perched atop the undulating hills of Radda in Chianti, Villa Pancho is a picturesque, panoramic home with views of olive ...

    From $3385 per night (USD)

    Expedia

    Details
  • My Rental Homes - Villa Torre del Chianti with hited pool, Gym and wellness center
    From $4716 per night (USD)

    VRBO

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

    Bedrooms:
    6
    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 $4716 per night (USD)

    VRBO

    Details
  • Crognole 6, Emma Villas
    From $723 per night (USD)

    Expedia

    Crognole 6, Emma Villas

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

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

    From $723 per night (USD)

    Expedia

    Details
  • Il Poggetto a Vescinino, Radda in Chianti, Siena and Chianti
    From $252 per night (USD)

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Tucked away behind trees, yet opening out onto breathtaking hillside views, this charming country villa is an escapist’s ...

    From $252 per night (USD)

    VRBO

    Details
  • La Casa di Radda, Radda in Chianti, Siena and Chianti
    From $380 per night (USD)

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    A sleek and charming bungalow in the town of Radda in Chianti, La Casa di Radda is a lovely getaway for 5 people. It’s a ...

    From $380 per night (USD)

    Expedia

    Details
  • Casino di Vescine, Radda in Chianti, Siena and Chianti
    From $488 per night (USD)

    VRBO

    Casino di Vescine, Radda in Chianti, Siena and Chianti

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Looking for a truly spacious and well-located villa? Look no further, because this old stone house offers more than enou ...

    From $488 per night (USD)

    VRBO

    Details
  • Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
    From $862 per night (USD)

    Expedia

    Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    A delicate balance of rustic farmhouse style and modern comfort, Tenuta Lo Spugno is an extraordinary, and thoroughly pr ...

    From $862 per night (USD)

    Expedia

    Details
  • Vivaio, Radda in Chianti, Siena and Chianti
    From $1044 per night (USD)

    VRBO

    Vivaio, Radda in Chianti, Siena and Chianti

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    Set in a vast garden with lush lawns and trees, this villa is a superb place to host a gathering of family or friends wh ...

    From $1044 per night (USD)

    VRBO

    Details
  • Uva, Ceperano, Radda in Chianti, Siena and Chianti
    From $159 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 $159 per night (USD)

    Expedia

    Details
  • Il Casetto, Radda in Chianti, Siena and Chianti
    From $765 per night (USD)

    VRBO

    Il Casetto, Radda in Chianti, Siena and Chianti

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    A stunning old stone villa in a beautiful location, Il Casetto has been exquisitely reinterpreted in its design and deco ...

    From $765 per night (USD)

    VRBO

    Details
  • Casa Ceperano, Radda in Chianti, Siena and Chianti
    From $807 per night (USD)

    Expedia

    Casa Ceperano, Radda in Chianti, Siena and Chianti

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    12

    A traditional Tuscan farmhouse in expansive grounds and surrounded by olive groves and vineyards, Casa Ceperano has been ...

    From $807 per night (USD)

    Expedia

    Details
  • La Casanova, Radda in Chianti, Siena and Chianti
    From $167 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 $167 per night (USD)

    VRBO

    Details
  • Il Boschetto, Radda in Chianti, Siena and Chianti
    From $293 per night (USD)

    Expedia

    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 $293 per night (USD)

    Expedia

    Details
  • Ulivo, Ceperano, Radda in Chianti, Siena and Chianti
    From $83 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 $83 per night (USD)

    VRBO

    Details
  • Girasole, Ceperano, Radda in Chianti, Siena and Chianti
    From $139 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 $139 per night (USD)

    Expedia

    Details
  • Angolino, Radda in Chianti, Siena and Chianti
    From $288 per night (USD)

    VRBO

    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 $288 per night (USD)

    VRBO

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

    Expedia

    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 $171 per night (USD)

    Expedia

    Details
  • Casa di Pesa, Radda in Chianti, Siena and Chianti
    From $282 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 $282 per night (USD)

    VRBO

    Details
  • Calafralina, Radda in Chianti, Siena and Chianti
    From $614 per night (USD)

    Expedia

    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 $614 per night (USD)

    Expedia

    Details
  • Stone Farmhouse in Chianti Hill between Florence, Siena private veranda and lake
    From $196 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 $196 per night (USD)

    VRBO

    Details
  • Castellare Petroso, Radda in Chianti, Siena and Chianti
    From $630 per night (USD)

    Expedia

    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 $630 per night (USD)

    Expedia

    Details
  • Le Bonatte by Interhome
    From $137 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 $137 per night (USD)

    VRBO

    Details
  • Le Bonatte by Interhome
    From $332 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 $332 per night (USD)

    Expedia

    Details
  • Private Villa with A\/C, private pool, WIFI, TV, patio, pets allowed, panoramic view, parking
    From $317 per night (USD)

    VRBO

    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 $317 per night (USD)

    VRBO

    Details
  • Poggio della Villa, Radda in Chianti, Siena and Chianti
    From $374 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 $374 per night (USD)

    Expedia

    Details
  • Private Villa with WIFI, private pool, A\/C, TV, patio, pets allowed, panoramic view, parking
    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

    Details
  • Villa Radda - 11 Guests
    From $4972 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 $4972 per night (USD)

    Expedia

    Details
  • Belvilla by OYO Uva
    From $162 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 $162 per night (USD)

    VRBO

    Details
  • Belvilla by OYO Limone
    From $188 per night (USD)

    Expedia

    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 $188 per night (USD)

    Expedia

    Details
  • Casa Momi - One Bedroom Villa, Sleeps 2
    From $451 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 $451 per night (USD)

    VRBO

    Details
  • Cottage \Podere in Volpaia\ with Garden & Wi-Fi
    From $203 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 $203 per night (USD)

    Expedia

    Details
  • Apartment 'Rifugio sulla via di Volpaia' with Private Terrace, Wi-Fi and Air Conditioning
    From $254 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 $254 per night (USD)

    VRBO

    Details
  • Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
    From $1898 per night (USD)

    Expedia

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

    Bedrooms:
    3
    Bathrooms:
    6
    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 $1898 per night (USD)

    Expedia

    Details
  • La Capanna - Radda in Chianti. Newly renovated \nstone farmhouse with pool & A\/C
    From $481 per night (USD)

    VRBO

    La Capanna - Radda in Chianti. Newly renovated \nstone 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 $481 per night (USD)

    VRBO

    Details
  • Villa Poggio la Croce by MMega
    From $818 per night (USD)

    Expedia

    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 Chi ...

    From $818 per night (USD)

    Expedia

    Details
  • Chianti  Apt Private Panoramic Garden, Radda in Chianti, Italy
    From $233 per night (USD)

    VRBO

    Chianti Apt Private Panoramic Garden, Radda in Chianti, Italy

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Immerse yourself in the beauty of Chianti Hills at this 2-bedroom apartment surrounded by vineyards and lush greenery. ...

    From $233 per night (USD)

    VRBO

    Details
  • Rosa di Chianti, Radda in Chianti, Siena and Chianti
    From $507 per night (USD)

    Expedia

    Rosa di Chianti, Radda in Chianti, Siena and Chianti

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Discover a homely, Tuscan-style country cottage nestled between the charming Chianti towns of Castellina and Radda. This ...

    From $507 per night (USD)

    Expedia

    Details
  • Casa Susanna, Radda in Chianti, Italy
    Click For Pricing

    VRBO

    Casa Susanna, Radda in Chianti, Italy

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    This rustic cottage, on the edge of the charming village of Volpaia, is an idyllic spot for a couple or family who want ...

    Click For Pricing

    VRBO

    Details
  • Villa del Poggio by Interhome
    From $278 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 $278 per night (USD)

    Expedia

    Details
  • Home 'Serena, Radda In Chianti' with Private Pool, Private Terrace and Wi-Fi
    From $226 per night (USD)

    VRBO

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

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $226 per night (USD)

    VRBO

    Details
  • Stunning private villa with WIFI, private pool, TV, patio and parking, close to Greve In Chianti
    From $964 per night (USD)

    Expedia

    Stunning private villa with WIFI, private pool, TV, patio and parking, close to Greve In Chianti

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    Villa Poggio La Croce is a beautiful stone building (400 sq m) with WiFi internet and private pool. The property can ac ...

    From $964 per night (USD)

    Expedia

    Details
  • Fox's Well Villa
    From $846 per night (USD)

    VRBO

    Fox's Well Villa

    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 $846 per night (USD)

    VRBO

    Details
  • Luxury Villa in Tuscany for 10 People
    From $4128 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 $4128 per night (USD)

    Expedia

    Details
  • Villa Pianvecchio by Fantasia Villas
    From $4601 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 $4601 per night (USD)

    VRBO

    Details
  • Villa Montemaggio by Fantasia Villas
    From $1260 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 $1260 per night (USD)

    VRBO

    Details
  • Villa Castiglioni by Fantasia Villas
    From $4578 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 $4578 per night (USD)

    VRBO

    Details
  • Luxury Villa in Radda Chianti,heatable Pool,Aircon,SPA room,gym room,sleep 10
    From $2452 per night (USD)

    VRBO

    Luxury Villa in Radda Chianti,heatable Pool,Aircon,SPA room,gym room,sleep 10

    Bedrooms:
    8
    Bathrooms:
    6
    Sleeps:
    12

    This charming wine estate with panoramic views is located on the hills at just 1.5 km from Radda in Chianti, a lovely me ...

    From $2452 per night (USD)

    VRBO

    Details
  • Fiorita In Radda in Chianti, Tuscany
    From $423 per night (USD)

    VRBO

    Fiorita In Radda in Chianti, Tuscany

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Property for exclusive use Typical country house in stone, 150 sq. m., with 4 double bedrooms and 3 bathrooms, holding u ...

    From $423 per night (USD)

    VRBO

    Details
  • Il Torrino In Radda in Chianti, Tuscany
    From $726 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 $726 per night (USD)

    VRBO

    Details
  • Docciole: Chianti Villa and Pool for 12
    From $525 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 $525 per night (USD)

    VRBO

    Details
  • L'Angolino In Radda in Chianti, Tuscany
    From $294 per night (USD)

    VRBO

    L'Angolino In Radda in Chianti, Tuscany

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Property for exclusive use Beautiful stone farmhouse, completely independent, 120 sq. m., holding up to 6 persons with t ...

    From $294 per night (USD)

    VRBO

    Details
  • Cosoli, Charming Two-story Historical Villa Situated In The Heart Of Chianti
    From $958 per night (USD)

    VRBO

    Cosoli, Charming Two-story Historical Villa Situated In The Heart Of Chianti

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    Cosoli is a family house and the main residence of the owners. It is ideally located right in the middle of Chianti Clas ...

    From $958 per night (USD)

    VRBO

    Details
  • An enchanting cottage for a perfect vacation
    From $156 per night (USD)

    VRBO

    An enchanting cottage for a perfect vacation

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Leccino is one of three houses that are part of Podere Pornanino, a 36-hectare organic farm producing extra virgin olive ...

    From $156 per night (USD)

    VRBO

    Details
  • Luxury Historic Villa San Piero, Panoramic Views, Romantic Chapel, Wine Cellar
    From $1643 per night (USD)

    VRBO

    Luxury Historic Villa San Piero, Panoramic Views, Romantic Chapel, Wine Cellar

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    10

    SAN PIERO: A private, luxury Villa embedded in Chianti vineyards with panoramic views, saltwater pool and a Chapel from ...

    From $1643 per night (USD)

    VRBO

    Details
  • Casale il Gualdo In Radda in Chianti, Tuscany
    From $726 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 $726 per night (USD)

    VRBO

    Details
  • Belvilla by OYO Villa Ulivo
    From $470 per night (USD)

    VRBO

    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 $470 per night (USD)

    VRBO

    Details
  • A paradise of cypress and olive trees
    From $256 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 $256 per night (USD)

    VRBO

    Details
  • Villa Cavallari Comfortable holiday residence
    From $3780 per night (USD)

    VRBO

    Villa Cavallari Comfortable holiday residence

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    Wonderful villa with 2 dependances, infinity pool and private garden, immersed in the Tuscan countryside, near Radda in ...

    From $3780 per night (USD)

    VRBO

    Details
  • Casa Marina, Radda in Chianti, Siena and Chianti
    From $220 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 $220 per night (USD)

    Expedia

    Details
  • Fico del Corno, Radda in Chianti, Siena and Chianti
    From $271 per night (USD)

    VRBO

    Fico del Corno, Radda in Chianti, Siena and Chianti

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    A magnificently positioned cottage, situated in the heart of the Chianti area. Fico del Corno effortlessly blends the 19 ...

    From $271 per night (USD)

    VRBO

    Details
  • Villa 'Le Rondini' with Mountain View, Private Pool and Wi-Fi
    From $3462 per night (USD)

    Expedia

    Villa 'Le Rondini' with Mountain View, Private Pool and Wi-Fi

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    The villa Le Rondini in Siena is the ideal accommodation for a relaxing holiday with a mountain view. The 3-storey prope ...

    From $3462 per night (USD)

    Expedia

    Details
  • Charming Villa W\/ Private Pool in Heart of Chianti
    From $1127 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 $1127 per night (USD)

    VRBO

    Details
  • Villa Pianodolce - Radda In Chianti
    From $4972 per night (USD)

    Expedia

    Villa Pianodolce - Radda In Chianti

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

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

    From $4972 per night (USD)

    Expedia

    Details
  • Villa Pianodolce - Radda In Chianti
    From $4002 per night (USD)

    VRBO

    Villa Pianodolce - Radda In Chianti

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

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

    From $4002 per night (USD)

    VRBO

    Details
  • 4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
    From $876 per night (USD)

    Expedia

    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 $876 per night (USD)

    Expedia

    Details
  • Chianti dreaming in Radda
    From $353 per night (USD)

    VRBO

    Chianti dreaming in Radda

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    <p>Situated in a village, this welcoming apartment brings all of Radda in Chianti within your reach. With convenient ons ...

    From $353 per night (USD)

    VRBO

    Details
  • Luxury Tuscany villa
    From $4303 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 $4303 per night (USD)

    VRBO

    Details
  • Belvilla by OYO Farmhouse in Radda with Garden
    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

    Details
  • Chianti villa rental
    From $5351 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 $5351 per night (USD)

    VRBO

    Details
  • Villa Al Borgo: A welcoming two-story villa located in a characteristic village, with Free WI-FI.
    From $977 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 $977 per night (USD)

    VRBO

    Details
  • Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
    From $1398 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 $1398 per night (USD)

    Expedia

    Details
  • Case Domine, Radda in Chianti, Siena and Chianti
    Click For Pricing

    VRBO

    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 Pricing

    VRBO

    Details
  • Cielo di Radda, Radda in Chianti, Siena and Chianti
    From $612 per night (USD)

    Expedia

    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 $612 per night (USD)

    Expedia

    Details
  • Beautiful private villa for 14 guests with WIFI, private pool, TV, terrace, pets allowed and par...
    From $534 per night (USD)

    VRBO

    Beautiful private villa for 14 guests with WIFI, private pool, 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 $534 per night (USD)

    VRBO

    Details
  • Holiday Home 'Beretone' with Mountain View, Wi-Fi and Air Conditioning
    From $210 per night (USD)

    Expedia

    Holiday Home 'Beretone' with Mountain View, Wi-Fi and Air Conditioning

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Overlooking the mountain, the holiday home "Beretone" in Radda in Chianti impresses guests with its fantastic views. The ...

    From $210 per night (USD)

    Expedia

    Details
  • Villa Tower House Fattoria di Montemaggio
    From $1400 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 $1400 per night (USD)

    VRBO

    Details
  • Villa Cavallari by MMega
    From $1390 per night (USD)

    Expedia

    Villa Cavallari by MMega

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    External Description Villa Cavallari is a large rural property (main house + 2 dependances) immersed in the Chianti cou ...

    From $1390 per night (USD)

    Expedia

    Details
  • Villa in Radda In Chianti with 6 bedrooms sleeps 12
    From $3467 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 $3467 per night (USD)

    VRBO

    Details
  • Fienile al Corno, Radda in Chianti, Siena and Chianti
    From $323 per night (USD)

    Expedia

    Fienile al Corno, Radda in Chianti, Siena and Chianti

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Wine buffs will love this charming old stone villa in the heart of Chianti Classico. Dump the bags, jump in the sparklin ...

    From $323 per night (USD)

    Expedia

    Details
  • Casale Al Sole Tra Le Vecchie Vigne 6, Radda in Chianti, Italy
    From $378 per night (USD)

    VRBO

    Casale Al Sole Tra Le Vecchie Vigne 6, 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 $378 per night (USD)

    VRBO

    Details
  • Casale Al Sole Tra Le Vecchie Vigne 10, Radda in Chianti, Italy
    From $581 per night (USD)

    Expedia

    Casale Al Sole Tra Le Vecchie Vigne 10, Radda in Chianti, Italy

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Amidst the green and wooded hills of the Chianti gallo nero lies Casale al sole tra le vecchie vigne, an old farmhouse d ...

    From $581 per night (USD)

    Expedia

    Details
  • [The Garden in Chianti] Peace-Relax-Pool
    Click For Pricing

    VRBO

    [The Garden in Chianti] Peace-Relax-Pool

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    <p>Situated in a village, this welcoming vacation home brings all of Radda in Chianti within your reach. With convenient ...

    Click For Pricing

    VRBO

    Details
  • [La Terrazza nel Chianti] Peace-Relax-Pool
    Click For Pricing

    Expedia

    [La Terrazza nel Chianti] Peace-Relax-Pool

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

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

    Click For Pricing

    Expedia

    Details