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  • The Gelda house, relax with a view
    From $123 per night (USD)

    VRBO

    The Gelda house, relax with a view

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The House Gelda is on the second floor of a building in a scenic stone. In fact, opening the window of the room we are f ...

    From $123 per night (USD)

    VRBO

    Details
  • Goccia in Valdorcia Smart Home
    From $116 per night (USD)

    Expedia

    Goccia in Valdorcia Smart Home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Located in the "new" part of San Quirico d'Orcia, just 5 minutes walk from the town centre, the apartment is on the grou ...

    From $116 per night (USD)

    Expedia

    Details
  • pleasant characteristic farmhouse in a part of the Chianti ideal for visiting the most important towns
    From $590 per night (USD)

    VRBO

    pleasant characteristic farmhouse in a part of the Chianti ideal for visiting the most important towns

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    (Text automatically translated) The farmhouse is situated on a hill and is surrounded by a fenced-in area with views of ...

    From $590 per night (USD)

    VRBO

    Details
  • Villa Mulinello, secluded, panoramic view over Montepulciano valley.
    From $251 per night (USD)

    Expedia

    Villa Mulinello, secluded, panoramic view over Montepulciano valley.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    90m2, accommodates 6 guests. The original building, a 17th-century tower house, was restored in 1990 according to the Tu ...

    From $251 per night (USD)

    Expedia

    Details
  • Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
    From $306 per night (USD)

    VRBO

    Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The hayloft is situated on a gently rolling hill and is sourrounded by a large fenced-in outdoor area with views on the ...

    From $306 per night (USD)

    VRBO

    Details
  • Villa Banditello, secluded, panoramic view over Montepulciano valley.
    From $262 per night (USD)

    Expedia

    Villa Banditello, secluded, panoramic view over Montepulciano valley.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Villa BANDITELLO, 130m2, accommodates 6 guests. The original building, dating back to the early 20th century, was restor ...

    From $262 per night (USD)

    Expedia

    Details
  • Farmhouse  'Podere San Giusto' di Sovicille
    From $316 per night (USD)

    VRBO

    Farmhouse 'Podere San Giusto' di Sovicille

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    The apartament is completely renovated with a special care to detail in a meeting between traditional style and modern c ...

    From $316 per night (USD)

    VRBO

    Details
  • Restored barn in beautiful house with swimming pool, 10 minutes from Siena
    From $128 per night (USD)

    Expedia

    Restored barn in beautiful house with swimming pool, 10 minutes from Siena

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Bascia ...

    From $128 per night (USD)

    Expedia

    Details
  • Antico Podere La Martinella- Ground floor apartment
    From $90 per night (USD)

    VRBO

    Antico Podere La Martinella- Ground floor apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Antico Podere renovated in an old style, but with modern comforts. Less than a km from the inhabited center Modern comfo ...

    From $90 per night (USD)

    VRBO

    Details
  • Ancient farm la Martinella Depandance apartment
    From $83 per night (USD)

    Expedia

    Ancient farm la Martinella Depandance apartment

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Antico Podere renovated in an old style, but with modern comforts. Less than a km from the inhabited center Modern comfo ...

    From $83 per night (USD)

    Expedia

    Details
  • Antico Podere La Martinella- First floor apartment
    From $85 per night (USD)

    VRBO

    Antico Podere La Martinella- First floor apartment

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Antico Podere renovated in an old style, but with modern comforts. Less than a km from the inhabited center Modern comfo ...

    From $85 per night (USD)

    VRBO

    Details
  • Podere Bagnolo 8, Emma Villas
    From $674 per night (USD)

    Expedia

    Podere Bagnolo 8, Emma Villas

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

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

    From $674 per night (USD)

    Expedia

    Details
  • Il Poggio dell'Eremita
    From $146 per night (USD)

    VRBO

    Il Poggio dell'Eremita

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Ideal for three people, the villa is surrounded by olive groves and immersed among the Tuscan hills in the heart of Vald ...

    From $146 per night (USD)

    VRBO

    Details
  • House in a typical village in the heart of Chianti
    From $91 per night (USD)

    Expedia

    House in a typical village in the heart of Chianti

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Located in a pretty and peaceful village on the top of a hill in the Chianti area which overlooks a landscape of olive t ...

    From $91 per night (USD)

    Expedia

    Details
  • CHARMING APARTMENT WITH POOL - 40 KM FLORENCE, 20 KM SIENA, 15 KM S. GIMIGNANO
    From $247 per night (USD)

    VRBO

    CHARMING APARTMENT WITH POOL - 40 KM FLORENCE, 20 KM SIENA, 15 KM S. GIMIGNANO

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The apartment is located on the 1st floor of our beautiful country house with an independent entrance accessible via a b ...

    From $247 per night (USD)

    VRBO

    Details
  • Guest House in Villa with pool, terrace, walks, 10 min. Siena, Chianti.
    From $128 per night (USD)

    Expedia

    Guest House in Villa with pool, terrace, walks, 10 min. Siena, Chianti.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Bascia ...

    From $128 per night (USD)

    Expedia

    Details
  • House in a typical village in the heart of Chianti
    From $98 per night (USD)

    VRBO

    House in a typical village in the heart of Chianti

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Apartment located in a pretty and peaceful village on the top of a hill in the Chianti area which overlooks a landscape ...

    From $98 per night (USD)

    VRBO

    Details
  • San Gimignano Town Garden - 10 pax
    From $609 per night (USD)

    Expedia

    San Gimignano Town Garden - 10 pax

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    San Gimignano Town Garden is a one in a million apartment characterized by a central location and wide internal spaces, ...

    From $609 per night (USD)

    Expedia

    Details
  • Il Casale by Interhome
    From $182 per night (USD)

    VRBO

    Il Casale by Interhome

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This typical country house is part of a small hamlet in the middle of the untouched nature of the "Alta Meremma" nature ...

    From $182 per night (USD)

    VRBO

    Details
  • Il Cardo by Interhome
    From $119 per night (USD)

    Expedia

    Il Cardo by Interhome

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Farmhouse "Il Pero di Cetinale". 12 apartments in the property. 17 km from the centre of Siena, 76 km from the centre of ...

    From $119 per night (USD)

    Expedia

    Details
  • Il Ligustro by Interhome
    From $69 per night (USD)

    VRBO

    Il Ligustro by Interhome

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Farmhouse "Il Pero di Cetinale". 12 apartments in the property. 17 km from the centre of Siena, 76 km from the centre of ...

    From $69 per night (USD)

    VRBO

    Details
  • CASAVOLTA Studio in Borgo WIFI/conditioning
    Click For Pricing

    Expedia

    CASAVOLTA Studio in Borgo WIFI/conditioning

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    CASAVOLTA is a newly renovated studio in the heart of an 800 years old Borgo Independent entrance, double bedroom with ...

    Click For Pricing

    Expedia

    Details
  • La Ginestra by Interhome
    From $142 per night (USD)

    VRBO

    La Ginestra by Interhome

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Farmhouse "Il Pero di Cetinale". 12 apartments in the property. 17 km from the centre of Siena, 76 km from the centre of ...

    From $142 per night (USD)

    VRBO

    Details
  • La Tinaia by Interhome
    From $122 per night (USD)

    Expedia

    La Tinaia by Interhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Old farmhouse, renovated, with lovely view on the hills of Chianti Classico. Surrounded by vineyards. In the property th ...

    From $122 per night (USD)

    Expedia

    Details
  • L'Erika by Interhome
    From $69 per night (USD)

    VRBO

    L'Erika by Interhome

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Farmhouse "Il Pero di Cetinale". 12 apartments in the property. 17 km from the centre of Siena, 76 km from the centre of ...

    From $69 per night (USD)

    VRBO

    Details
  • Podere S Giovanni by Interhome
    From $419 per night (USD)

    Expedia

    Podere S Giovanni by Interhome

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Recently renovated farmhouse, divided into two independent apartments, but let as one unit. Panoramic position, 3 km fro ...

    From $419 per night (USD)

    Expedia

    Details
  • Il Valacchio by Interhome
    From $150 per night (USD)

    VRBO

    Il Valacchio by Interhome

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Simple farmhouse "Il Valacchio", 2 storeys, semi-detached. 5 km from the centre of Sovicille, 14 km from the centre of S ...

    From $150 per night (USD)

    VRBO

    Details
  • Val d'Orcia by Interhome
    From $416 per night (USD)

    Expedia

    Val d'Orcia by Interhome

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Country house "Val d'Orcia", 580 m a.s.l., detached, surrounded by fields and vineyards. Below Radicofani, in a sunny po ...

    From $416 per night (USD)

    Expedia

    Details
  • Le Buche by Interhome
    From $188 per night (USD)

    VRBO

    Le Buche by Interhome

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Chianti Classico 14 km from Castellina in Chianti: Dated back to the 1600, is surrounded by the magnificent Tuscan lands ...

    From $188 per night (USD)

    VRBO

    Details
  • Mulinaccio di Badia, Gaiole in Chianti, Siena and Chianti
    From $676 per night (USD)

    Expedia

    Mulinaccio di Badia, Gaiole in Chianti, Siena and Chianti

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    8

    Mulinaccio di Badia is a charming holiday home set in the gentle hills of the Chianti Classico, surrounded by vineyards ...

    From $676 per night (USD)

    Expedia

    Details
  • Capanna di Sopra by Interhome
    From $144 per night (USD)

    VRBO

    Capanna di Sopra by Interhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Old farmhouse, renovated, with lovely view on the hills of Chianti Classico. Surrounded by vineyards. In the property th ...

    From $144 per night (USD)

    VRBO

    Details
  • Vanessa by Interhome
    From $139 per night (USD)

    Expedia

    Vanessa by Interhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Podere S.Giuseppe, 1 km from Castelnuovo Berardenga: Podere San Giuseppe, situated in a magnificent panoramic position w ...

    From $139 per night (USD)

    Expedia

    Details
  • L´Azalea by Interhome
    From $146 per night (USD)

    VRBO

    L´Azalea by Interhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The restored country estate "L'Azalea" is in a panoramic position surrounded by its own vineyards and olive groves. Beau ...

    From $146 per night (USD)

    VRBO

    Details
  • Casa Frati by Interhome
    From $388 per night (USD)

    Expedia

    Casa Frati by Interhome

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    3 km from Castiglion d'Orcia: This former small monastery with wonderful views over the Orcia valley in the southern pro ...

    From $388 per night (USD)

    Expedia

    Details
  • L'Agrifoglio by Interhome
    From $119 per night (USD)

    VRBO

    L'Agrifoglio by Interhome

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Farmhouse "Il Pero di Cetinale". 12 apartments in the property. 17 km from the centre of Siena, 76 km from the centre of ...

    From $119 per night (USD)

    VRBO

    Details
  • Vineyard View by Interhome
    From $915 per night (USD)

    Expedia

    Vineyard View by Interhome

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Large, child friendly, beautiful villa, surrounded by meadows. 7 km from the centre of San Gimignano, 52 km from the cen ...

    From $915 per night (USD)

    Expedia

    Details
  • Capanna di Sotto by Interhome
    From $119 per night (USD)

    VRBO

    Capanna di Sotto by Interhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Old farmhouse, renovated, with lovely view on the hills of Chianti Classico. Surrounded by vineyards. In the property th ...

    From $119 per night (USD)

    VRBO

    Details
  • Il Nocciolo by Interhome
    From $136 per night (USD)

    Expedia

    Il Nocciolo by Interhome

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Farmhouse "Il Pero di Cetinale". 12 apartments in the property. 17 km from the centre of Siena, 76 km from the centre of ...

    From $136 per night (USD)

    Expedia

    Details
  • Le Bonatte by Interhome
    From $171 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 $171 per night (USD)

    VRBO

    Details
  • San Biagio by Interhome
    From $137 per night (USD)

    Expedia

    San Biagio by Interhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Country house "Rapolano", renovated, surrounded by fields. 1.5 km from the centre of Rapolano Terme, 25 km from the cent ...

    From $137 per night (USD)

    Expedia

    Details
  • Casale Il Poggino by Interhome
    From $721 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 $721 per night (USD)

    VRBO

    Details
  • Le Buche by Interhome
    From $87 per night (USD)

    Expedia

    Le Buche by Interhome

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Chianti Classico 14 km from Castellina in Chianti: Dated back to the 1600, is surrounded by the magnificent Tuscan lands ...

    From $87 per night (USD)

    Expedia

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

    VRBO

    Rapolano by Interhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Country house "Rapolano", renovated, surrounded by fields. 1.5 km from the centre of Rapolano Terme, 25 km from the cent ...

    From $137 per night (USD)

    VRBO

    Details
  • Ciliegio by Interhome
    From $167 per night (USD)

    Expedia

    Ciliegio by Interhome

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Chianti Classico 14 km from Castellina in Chianti: Dated back to the 1600, is surrounded by the magnificent Tuscan lands ...

    From $167 per night (USD)

    Expedia

    Details
  • Il Forno by Interhome
    From $190 per night (USD)

    VRBO

    Il Forno by Interhome

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Chianti Classico 14 km from Castellina in Chianti: Dated back to the 1600, is surrounded by the magnificent Tuscan lands ...

    From $190 per night (USD)

    VRBO

    Details
  • Le Buche by Interhome
    From $83 per night (USD)

    Expedia

    Le Buche by Interhome

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Chianti Classico 14 km from Castellina in Chianti: Dated back to the 1600, is surrounded by the magnificent Tuscan lands ...

    From $83 per night (USD)

    Expedia

    Details
  • Wonderful  villa for 5 people with pool, WIFI, TV and patio
    From $235 per night (USD)

    VRBO

    Wonderful villa for 5 people with pool, WIFI, TV and patio

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Casa Di Giulio is located in Vivo D'orcia, Italy and only 34 km (21 mi) from Montalcino in the tourist area "Orcia Valle ...

    From $235 per night (USD)

    VRBO

    Details
  • Wonderful private villa for 4 people with pool, WIFI and TV
    From $214 per night (USD)

    Expedia

    Wonderful private villa for 4 people with pool, WIFI and TV

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Conveniently located in Vivo D'orcia, Italy in the tourist area "Orcia Valley" and only 34 km (21 mi) from Montalcino. C ...

    From $214 per night (USD)

    Expedia

    Details
  • VILLA LA COCCOLA WITH HEATED POOL AND HYDROMASSAGE 3 rooms en suite
    From $499 per night (USD)

    VRBO

    VILLA LA COCCOLA WITH HEATED POOL AND HYDROMASSAGE 3 rooms en suite

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Villa La Coccola is a seductive newly renovated farmhouse whose oldest part dates back to 1700, Leaning against a terrac ...

    From $499 per night (USD)

    VRBO

    Details
  • Your home in Trequanda
    From $98 per night (USD)

    Expedia

    Your home in Trequanda

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Fully equipped and recently refurbished (2016) apartment for up to 4 people overlooking the main square in the center of ...

    From $98 per night (USD)

    Expedia

    Details
  • Holiday apartment mit Pool und Terrasse
    From $142 per night (USD)

    VRBO

    Holiday apartment mit Pool und Terrasse

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The holiday apartment is located in an apartment house built in 1700, was renovated in 2008 and is furnished in a functi ...

    From $142 per night (USD)

    VRBO

    Details
  • 3 Central Apts Connected with Courtyard - Duomo Area
    Click For Pricing

    Expedia

    3 Central Apts Connected with Courtyard - Duomo Area

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    11

    This is a large apartment of 3 units connected to each other by an ancient charming courtyard. Each unit offers a bathro ...

    Click For Pricing

    Expedia

    Details
  • Villa in Montalcino with 5 bedrooms sleeps 10
    From $1466 per night (USD)

    VRBO

    Villa in Montalcino with 5 bedrooms sleeps 10

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Villa Lorian is a very comfortable Italian villa located amidst mature cypresses, rolling hills and the vineyards of Mon ...

    From $1466 per night (USD)

    VRBO

    Details
  • SUITE WINE - Relax & Design in the Heart of the Valdorcia
    From $112 per night (USD)

    Expedia

    SUITE WINE - Relax & Design in the Heart of the Valdorcia

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Vino Suite is an elegant apartment very comfortable and with attention to detail with modern style. 2 double bedrooms (o ...

    From $112 per night (USD)

    Expedia

    Details
  • --- CASA DEL FATTORE ---
    From $320 per night (USD)

    VRBO

    --- CASA DEL FATTORE ---

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    APPARTAMENTO DI CHARME CON PISCINA- 40 KM FIRENZE, 20 KM SIENA, 15 KM S. GIMIGNANO Appartamento si trova al 1. piano de ...

    From $320 per night (USD)

    VRBO

    Details
  • CHARMING APARTMENT WITH SWIMMING POOL 35 KM FLORENCE, 20 KM SIENA, 12 KM CHIANTI
    From $307 per night (USD)

    Expedia

    CHARMING APARTMENT WITH SWIMMING POOL 35 KM FLORENCE, 20 KM SIENA, 12 KM CHIANTI

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    APARTMENT OF CHARM WITH SWIMMING POOL 35 KM FLORENCE, 20 KM SIENA, 15 KM S. GIMIGNANO, 12 KM THE VINEYARDS OF CHIANTI. ...

    From $307 per night (USD)

    Expedia

    Details
  • Apartment Lari by Interhome
    From $214 per night (USD)

    VRBO

    Apartment Lari by Interhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Residence "Lari", 2 storeys, built in 2000. 10 apartments in the property. 5 km from the centre of San Gimignano, 30 km ...

    From $214 per night (USD)

    VRBO

    Details
  • Podere Gragnano 12, Emma Villas
    From $1026 per night (USD)

    Expedia

    Podere Gragnano 12, Emma Villas

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

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

    From $1026 per night (USD)

    Expedia

    Details
  • Villa in Trequanda with 5 bedrooms sleeps 10
    From $512 per night (USD)

    VRBO

    Villa in Trequanda with 5 bedrooms sleeps 10

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Typical restored Tuscan farmhouse, in an extraordinarily panoramic and peaceful position. The stone building has an inte ...

    From $512 per night (USD)

    VRBO

    Details
  • Villa in Castellina w. Pool, Garden & Winery
    From $1535 per night (USD)

    Expedia

    Villa in Castellina w. Pool, Garden & Winery

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    The Villa di Castellina is a villa in the heart of the Tuscan hills, located 3 km from the center of Castellina in Chian ...

    From $1535 per night (USD)

    Expedia

    Details
  • Great Room - Villa Andrea - Quadruple Delux
    From $244 per night (USD)

    VRBO

    Great Room - Villa Andrea - Quadruple Delux

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Farm stay in Castiglione d'Orcia with free breakfast and an outdoor pool An outdoor pool, a garden, and free breakfast a ...

    From $244 per night (USD)

    VRBO

    Details
  • Villa Belle Vue: a Charm
    From $1074 per night (USD)

    VRBO

    Villa Belle Vue: a Charm

    Bedrooms:
    11
    Bathrooms:
    7
    Sleeps:
    14

    Villa Belle Vue is more than a countryside escape—it’s a gateway to Montalcino’s rich culture, cuisine, and natural beau ...

    From $1074 per night (USD)

    VRBO

    Details
  • Very exclusive Villa for 18 in Tuscany: corporate events, weddings
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    VRBO

    Very exclusive Villa for 18 in Tuscany: corporate events, weddings

    Bedrooms:
    9
    Bathrooms:
    9
    Sleeps:
    18

    Villa Bellissima VI is a destination like no other, combining the beauty and history of Tuscany in a tranquil setting wh ...

    Click For Pricing

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    Details
  • Prestigious detached villa with fireplace recently renovated.
    From $116 per night (USD)

    Expedia

    Prestigious detached villa with fireplace recently renovated.

    Bedrooms:
    0
    Bathrooms:
    2
    Sleeps:
    4

    Independent house in an ancient village of the '900, located 10 km from the center of Siena (15 minutes by car). Just r ...

    From $116 per night (USD)

    Expedia

    Details
  • Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
    From $424 per night (USD)

    VRBO

    Splendid farmhouse in Val d'Orcia with private swimming pool and sauna

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    9

    <p>A short distance from ecotours, cycling, and more, this family-friendly vacation home lets you experience it all. Wit ...

    From $424 per night (USD)

    VRBO

    Details
  • Casa Buonsignori - Apartment in historical center of Siena
    From $108 per night (USD)

    Expedia

    Casa Buonsignori - Apartment in historical center of Siena

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Inside the medieval walls of Siena, in the most ancient part of the city, across the street from the Pinacoteca Nationa ...

    From $108 per night (USD)

    Expedia

    Details
  • Independent flat 2 pax downstairs, in Villa, Siena View, Pool A/C, organic Farm
    From $140 per night (USD)

    VRBO

    Independent flat 2 pax downstairs, in Villa, Siena View, Pool A/C, organic Farm

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Independent apartment, on the ground floor, in a comfortable typical Tuscan Villa / Casale. Podere Cartaio is in the Sie ...

    From $140 per night (USD)

    VRBO

    Details
  • Agriturismo Il Caggio - 1 double bedroom apartment A
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    Expedia

    Agriturismo Il Caggio - 1 double bedroom apartment A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Il Caggio is located a few minutes from Sovicille, immersed in the greenery of the Montagnola Senese, among ancient oaks ...

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    Expedia

    Details
  • San Girolamo by Interhome
    From $303 per night (USD)

    VRBO

    San Girolamo by Interhome

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Residence "San Girolamo". In the centre of San Gimignano 29 km from the centre of Volterra, 47 km from the centre of Sie ...

    From $303 per night (USD)

    VRBO

    Details
  • Apartment Lari by Interhome
    From $190 per night (USD)

    Expedia

    Apartment Lari by Interhome

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Residence "Lari", 2 storeys, built in 2000. 10 apartments in the property. 5 km from the centre of San Gimignano, 30 km ...

    From $190 per night (USD)

    Expedia

    Details
  • Farmhouse in the heart of the real chiantishire
    From $168 per night (USD)

    VRBO

    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 $168 per night (USD)

    VRBO

    Details
  • Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
    From $414 per night (USD)

    Expedia

    Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Domus Nannini - Siena Paradise Apartments offers this elegant and luxury house in Historic Palace, called Palazzo Nannin ...

    From $414 per night (USD)

    Expedia

    Details
  • Dimora del Poggio - cozy Tuscan apartment
    From $169 per night (USD)

    VRBO

    Dimora del Poggio - cozy Tuscan apartment

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Stay in the heart of San Quirico, in a central and quiet 900 ft² apartment. Overlooking the garden and characteristic sq ...

    From $169 per night (USD)

    VRBO

    Details
  • Le Bonatte by Interhome
    From $375 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 $375 per night (USD)

    Expedia

    Details
  • Exclusive Stone Tower.
    From $126 per night (USD)

    VRBO

    Exclusive Stone Tower.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Ancient stone Terratetto (Tower), finely renovated in recent years, fine finishes and LED lighting. It has 2 bedrooms an ...

    From $126 per night (USD)

    VRBO

    Details
  •  Domus Nannini SPA - Belvedere Loggia - Palazzo Nannini
    From $190 per night (USD)

    Expedia

    Domus Nannini SPA - Belvedere Loggia - Palazzo Nannini

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Domus Nannini - Siena Paradise Apartments offers this elegant apartment in Historic Palace of 1400 called Palazzo Nannin ...

    From $190 per night (USD)

    Expedia

    Details
  • Apartment Casa Ravacciano with Wi-Fi & A/C
    From $118 per night (USD)

    VRBO

    Apartment Casa Ravacciano with Wi-Fi & A/C

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Located just 200m from the walls of the historic centre of Siena, the holiday apartment Casa Ravacciano has everything y ...

    From $118 per night (USD)

    VRBO

    Details
  • Acquerello Valdorcia Holiday House
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    Expedia

    Acquerello Valdorcia Holiday House

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    <p>Located in San Quirico d'Orcia, this welcoming vacation home brings it all within your reach. Horti Leonini and Palaz ...

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    Expedia

    Details
  • LA VINOVA Ancient House Walking Distance - A/C,  Private Patio & Panorama
    From $210 per night (USD)

    VRBO

    LA VINOVA Ancient House Walking Distance - A/C, Private Patio & Panorama

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    La Vinova it's a little ancient farmhouse with Wi-Fi and private patio with wide view on the Tuscan hills. The building ...

    From $210 per night (USD)

    VRBO

    Details
  • Villa dei 2 Ulivi (Abbadia Isola)
    From $573 per night (USD)

    VRBO

    Villa dei 2 Ulivi (Abbadia Isola)

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    23

    Our home is perfect for families or group of friends with kids to offer you peace and fantastic countryside location to ...

    From $573 per night (USD)

    VRBO

    Details
  • Large vacation villa rental in San Giovanni d'Asso
    From $1264 per night (USD)

    VRBO

    Large vacation villa rental in San Giovanni d'Asso

    Bedrooms:
    9
    Bathrooms:
    11
    Sleeps:
    21

    The Italian Villa 1 consists of two side-by-side villas in the charming Tuscan hilltown of San Giovanni d’Asso. The mai ...

    From $1264 per night (USD)

    VRBO

    Details
  • San Gimignano Dependance Rose's Rooms, with 4 rooms, full center, fast WiFi.
    From $357 per night (USD)

    Expedia

    San Gimignano Dependance Rose's Rooms, with 4 rooms, full center, fast WiFi.

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    9

    <p>You'll find bicycles, golfing, and more on site at this welcoming guesthouse. There's convenient onsite parking, so y ...

    From $357 per night (USD)

    Expedia

    Details
  • Fiammetta - Residence in an old Tuscan farmhouse near Montepulciano
    From $153 per night (USD)

    VRBO

    Fiammetta - Residence in an old Tuscan farmhouse near Montepulciano

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    The Fiammetta residence is a cozy 3-person accommodation perfect for a couple with a child. Furnished with antique furni ...

    From $153 per night (USD)

    VRBO

    Details
  • Wonderful private villa with private pool, WIFI, A/C, TV, patio, pets allowed and panoramic view
    From $357 per night (USD)

    Expedia

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

    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 $357 per night (USD)

    Expedia

    Details
  • Beautiful characteristic apartment with private garden, pool and parking
    From $290 per night (USD)

    VRBO

    Beautiful characteristic apartment with private garden, pool and parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    L 'apartment, called' The Times ', a name derived from the ceilings of an' old stables, is situated in a beautiful park ...

    From $290 per night (USD)

    VRBO

    Details
  • The Photographer's House
    From $106 per night (USD)

    Expedia

    The Photographer's House

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    3

    It is your home in Tuscany, furnished with the grace and love of those born there. It will allow you to breathe the fami ...

    From $106 per night (USD)

    Expedia

    Details
  • The Casetta di Brunello, quiet and breathtaking views
    From $196 per night (USD)

    VRBO

    The Casetta di Brunello, quiet and breathtaking views

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    "La Casetta di Brunello" is the latest creation of the Borghetto, created to welcome our guests in search of peace and r ...

    From $196 per night (USD)

    VRBO

    Details
  • Quaint and beautiful apartment with garden, pool and parking.
    From $258 per night (USD)

    Expedia

    Quaint and beautiful apartment with garden, pool and parking.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    L 'apartment, called' The Arches' is located in a beautiful park of a holiday home in Sinalunga's historic center and of ...

    From $258 per night (USD)

    Expedia

    Details
  • Stunning private villa for 11 people with WIFI, TV, balcony and pets allowed
    From $144 per night (USD)

    VRBO

    Stunning private villa for 11 people with WIFI, TV, balcony and pets allowed

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    11

    Property Summary Podere Casina is a detached farmhouse property situated just 600 meters from the charming village of Sc ...

    From $144 per night (USD)

    VRBO

    Details
  • CASA DEL MEDIOEVO
    From $117 per night (USD)

    VRBO

    CASA DEL MEDIOEVO

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    The entire apartment and the external courtyard are for the exclusive use of the guest. The apartment has been renovated ...

    From $117 per night (USD)

    VRBO

    Details
  • Stunning  villa for 10 guests with WIFI, private pool, TV, patio and panoramic view
    From $257 per night (USD)

    VRBO

    Stunning villa for 10 guests with WIFI, private pool, TV, patio and panoramic view

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Property Summary "Metallo" is a stunning semi-detached vacation rental located in the charming hamlet of Lano, just 10 k ...

    From $257 per night (USD)

    VRBO

    Details
  • Villa with pool in Chianti countryside
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    Expedia

    Villa with pool in Chianti countryside

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    <p>A short distance from ecotours, cycling, and more, this smoke-free villa lets you experience it all. With convenient ...

    Click For Pricing

    Expedia

    Details
  • Apartment With View - Right in City Center
    From $149 per night (USD)

    VRBO

    Apartment With View - Right in City Center

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p>A short distance from mountain biking, winery tours, and more, this smoke-free apartment lets you experience it all. ...

    From $149 per night (USD)

    VRBO

    Details
  • Casa Girolamo - Super Central with Private Parking
    From $147 per night (USD)

    Expedia

    Casa Girolamo - Super Central with Private Parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>Situated in a village, this welcoming apartment brings all of Montepulciano within your reach. Val di Chiana and Pala ...

    From $147 per night (USD)

    Expedia

    Details
  • Villetta Pia cottage in the vicinty of Bagni San Filippo
    From $132 per night (USD)

    VRBO

    Villetta Pia cottage in the vicinty of Bagni San Filippo

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Villa on the raised ground floor with private garden equipped with pergola and brick barbecue in a panoramic position on ...

    From $132 per night (USD)

    VRBO

    Details
  • relaxation between nature and history
    From $140 per night (USD)

    Expedia

    relaxation between nature and history

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Set in the Tuscan countryside between Siena and Grosseto, the Grancia del Santo is a small corner of paradise located in ...

    From $140 per night (USD)

    Expedia

    Details
  • Apartment in the castle, with restaurant and swimming pool, Ginestra
    From $126 per night (USD)

    VRBO

    Apartment in the castle, with restaurant and swimming pool, Ginestra

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Nice and comfortable apartment for 4 persons (70sqm), in the hamlet near the castle, about 200 meters from the swimming ...

    From $126 per night (USD)

    VRBO

    Details
  • Holiday House San Pierino -Capanna .. family holiday 15 minutes from Siena!
    From $274 per night (USD)

    VRBO

    Holiday House San Pierino -Capanna .. family holiday 15 minutes from Siena!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Affittacamere San Pierino is located in Monteroni d'Arbia, 16 km from Siena and 45 km from Arezzo. Free private on-site ...

    From $274 per night (USD)

    VRBO

    Details
  • VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
    From $7026 per night (USD)

    VRBO

    VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

    Bedrooms:
    8
    Bathrooms:
    7
    Sleeps:
    14

    A luxury, gorgeous recently restored Villa set in a unique countryside between Siena and Montalcino, to enjoy a wonderfu ...

    From $7026 per night (USD)

    VRBO

    Details
  • Casa del Dago apartment in the hear of Montalcino town
    From $269 per night (USD)

    Expedia

    Casa del Dago apartment in the hear of Montalcino town

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Casa del Dago is located in the historic center, a few meters from Piazza del Popolo, the beating heart of the medieval ...

    From $269 per night (USD)

    Expedia

    Details