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Results: 866 Rentals

  • Belvilla by OYO Typical country house with pool
    From $397 per night (USD)

    VRBO

    Belvilla by OYO Typical country house with pool

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Set in a countryside with views of the hills, this 2-bedroom villa accommodates 4 people. It is located in an isolated a ...

    From $397 per night (USD)

    VRBO

    Details
  • Villa Le Buche - Villa with private pool
    From $4803 per night (USD)

    Expedia

    Villa Le Buche - Villa with private pool

    Bedrooms:
    14
    Bathrooms:
    13
    Sleeps:
    26

    Villa Le Buche is a stunning vacation villa set on the grounds of a renowned wine and olive oil estate, just a few kilom ...

    From $4803 per night (USD)

    Expedia

    Details
  • La Querceta, Typical Residence. Last Minute Offer
    From $152 per night (USD)

    VRBO

    La Querceta, Typical Residence. Last Minute Offer

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Ideal geographical location, a few kilometers from Pienza, Montepulciano, and Montefollonico, with magnificent views of ...

    From $152 per night (USD)

    VRBO

    Details
  • Apartment on the first floor with a view of the village
    From $115 per night (USD)

    Expedia

    Apartment on the first floor with a view of the village

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This apartment (50 sqm) is on the first floor with a view of the countryside and the swimming pool with Torrita of Siena ...

    From $115 per night (USD)

    Expedia

    Details
  • Villa Porsenna in Chiusi
    From $589 per night (USD)

    VRBO

    Villa Porsenna in Chiusi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Immersed in the Chianti region and ideally located to discover Tuscany (Val d'Orcia, Montepulciano, Pienza, Montalcino, ...

    From $589 per night (USD)

    VRBO

    Details
  • Muffato 6, Emma Villas
    From $2015 per night (USD)

    Expedia

    Muffato 6, Emma Villas

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $2015 per night (USD)

    Expedia

    Details
  • L'Alcova 8+2, Emma Villas
    From $959 per night (USD)

    VRBO

    L'Alcova 8+2, Emma Villas

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

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

    From $959 per night (USD)

    VRBO

    Details
  • Charming House in the heart of Montepulciano
    From $150 per night (USD)

    Expedia

    Charming House in the heart of Montepulciano

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful charming flat, very romantic, ancient residence of the owner's great-grandfather, Notary of Montepulciano. Re ...

    From $150 per night (USD)

    Expedia

    Details
  • Podere Madonna Di Mezzo 6, Emma Villas
    From $873 per night (USD)

    VRBO

    Podere Madonna Di Mezzo 6, Emma Villas

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $873 per night (USD)

    VRBO

    Details
  • House / Villa - San Casciano dei Bagni
    From $147 per night (USD)

    Expedia

    House / Villa - San Casciano dei Bagni

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    (Text automatically translated) in the tranquility of the countryside between Siena and San Casciano dei Bagni cetona 15 ...

    From $147 per night (USD)

    Expedia

    Details
  • Bossoncina 8+1, Emma Villas
    From $1516 per night (USD)

    VRBO

    Bossoncina 8+1, Emma Villas

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    9

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

    From $1516 per night (USD)

    VRBO

    Details
  • Le Terre Di Nunzio 12, Emma Villas
    From $1131 per night (USD)

    Expedia

    Le Terre Di Nunzio 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 $1131 per night (USD)

    Expedia

    Details
  • Il Poderuccio 17, Emma Villas
    From $1490 per night (USD)

    VRBO

    Il Poderuccio 17, Emma Villas

    Bedrooms:
    9
    Bathrooms:
    10
    Sleeps:
    17

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

    From $1490 per night (USD)

    VRBO

    Details
  • House / Villa - Cetona
    From $146 per night (USD)

    Expedia

    House / Villa - Cetona

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    (Text automatically translated) in the heart of the countryside surrounded by green hills of Siena, on a single floor ho ...

    From $146 per night (USD)

    Expedia

    Details
  • Relax in a private Tuscan Villa with pool and open hill views
    From $1108 per night (USD)

    VRBO

    Relax in a private Tuscan Villa with pool and open hill views

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Nestled among vineyards and olive groves in the heart of the Val d'Orcis , this charming villa is the perfect retreat fo ...

    From $1108 per night (USD)

    VRBO

    Details
  • Charming & luxurious country villa, designer interiors, heated pool, great views
    From $975 per night (USD)

    Expedia

    Charming & luxurious country villa, designer interiors, heated pool, great views

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    A fully restored country villa has spectacular 360 degrees views of pastures, woods, olive groves, vineyards and medieva ...

    From $975 per night (USD)

    Expedia

    Details
  • Il Molinaccio 14+2, Emma Villas
    From $1480 per night (USD)

    VRBO

    Il Molinaccio 14+2, Emma Villas

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    16

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

    From $1480 per night (USD)

    VRBO

    Details
  • PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
    From $1745 per night (USD)

    Expedia

    PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

    Bedrooms:
    13
    Bathrooms:
    12
    Sleeps:
    24

    Villa Febea Historic Luxury Estate with Pool, Spa & Private Chapel in the Heart of Italy Step into the timeless eleganc ...

    From $1745 per night (USD)

    Expedia

    Details
  • Il Saragio open space in the Tuscan countryside
    From $139 per night (USD)

    VRBO

    Il Saragio open space in the Tuscan countryside

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Il Saragio is an open space of about 70 square meters obtained from the renovation of a farmhouse in the countryside of ...

    From $139 per night (USD)

    VRBO

    Details
  • Apartment on the first floor with a beautiful panoramic view, Air conditioning.
    From $141 per night (USD)

    Expedia

    Apartment on the first floor with a beautiful panoramic view, Air conditioning.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    his large flat (75sqm) is on the first floor and overlooks the garden and the olive groves. It consists of a living room ...

    From $141 per night (USD)

    Expedia

    Details
  •  House with private pool  with beautiful view Val d 'Orcia
    From $373 per night (USD)

    VRBO

    House with private pool with beautiful view Val d 'Orcia

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    The house has a private swimming pool for the exclusive use of one client. It is 1 km from the medieval village of Monti ...

    From $373 per night (USD)

    VRBO

    Details
  • Villa with private pool in the south-east of Tuscany
    From $513 per night (USD)

    VRBO

    Villa with private pool in the south-east of Tuscany

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    14

    Villa Donatella lies in the south-east part of the wonderful country-side of Tuscany. This lovely villa is situated on t ...

    From $513 per night (USD)

    VRBO

    Details
  • Villa Ardita: A characteristic and welcoming two-story villa surrounded by the greenery, with Free WI-FI.
    From $1491 per night (USD)

    VRBO

    Villa Ardita: A characteristic and welcoming two-story villa surrounded by the greenery, with Free WI-FI.

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    12

    Villa Ardita is a characteristic and welcoming two-story villa surrounded by the greenery. It sleeps 12 people. From Vil ...

    From $1491 per night (USD)

    VRBO

    Details
  • Palazzone, Torrita di Siena, Siena and Chianti
    From $1364 per night (USD)

    Expedia

    Palazzone, Torrita di Siena, Siena and Chianti

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    Encircled by lush flat lawns with incredible 360 degree views of mountains and forests, Palazzone is a grand stone villa ...

    From $1364 per night (USD)

    Expedia

    Details
  • Agriturismo San Giovanni
    From $922 per night (USD)

    VRBO

    Agriturismo San Giovanni

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    The family-run farmhouse maintains what is the spirit of this type of holiday where, if you wish, you can attend normal ...

    From $922 per night (USD)

    VRBO

    Details
  • Extremely panoramic villa with private swimming pool, large, well-equipped outdoor area, terrace wit
    From $554 per night (USD)

    Expedia

    Extremely panoramic villa with private swimming pool, large, well-equipped outdoor area, terrace wit

    Bedrooms:
    8
    Bathrooms:
    8
    Sleeps:
    18

    19th C. farmhouse surrounded by woods, olive groves and vineyards. A very attractive villa deriving from the complete re ...

    From $554 per night (USD)

    Expedia

    Details
  • Typical villa with private pool in a panoramic position in southern Tuscany, a few kilometres from t
    From $317 per night (USD)

    VRBO

    Typical villa with private pool in a panoramic position in southern Tuscany, a few kilometres from t

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    14

    Old farmhouse with the typical Tuscan architectural features. Il Poggiarone is a splendid farmhouse with typical Tuscan ...

    From $317 per night (USD)

    VRBO

    Details
  • Cottage with private swimming pool, outdoor Jacuzzi and air conditioning. Extremely panoramic positi
    From $268 per night (USD)

    Expedia

    Cottage with private swimming pool, outdoor Jacuzzi and air conditioning. Extremely panoramic positi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The holiday house Casa Cervognano, is plunged into a splendid landscape of silver olive groves and rows of vineyards, si ...

    From $268 per night (USD)

    Expedia

    Details
  • Casella Guest House - San Casciano dei Bagni-Palazzone
    From $371 per night (USD)

    VRBO

    Casella Guest House - San Casciano dei Bagni-Palazzone

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    At the topper floors of an historical wine cellar, Casella has been recently renovated bringing back to life the old Eig ...

    From $371 per night (USD)

    VRBO

    Details
  • Glicine - Agriturismo San Giovanni
    From $187 per night (USD)

    VRBO

    Glicine - Agriturismo San Giovanni

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The farm is family-run, which is what keeps the spirit of this type of holiday where, if you wish, you can attend the no ...

    From $187 per night (USD)

    VRBO

    Details
  • Duccio di Boninsegna Apartment - Agriturismo Renello
    From $446 per night (USD)

    VRBO

    Duccio di Boninsegna Apartment - Agriturismo Renello

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    DUCCIO from Boninsegna - 250 MQ- (4 + 2 beds) 2 double suites 2 large bathrooms with shower Living room with double sofa ...

    From $446 per night (USD)

    VRBO

    Details
  • Vitalba cottage with swimming pool
    From $385 per night (USD)

    VRBO

    Vitalba cottage with swimming pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    RENELLO We are a farmhouse in Tuscany near Pienza in the town of Trequanda (Siena), with an old farmhouse dating back t ...

    From $385 per night (USD)

    VRBO

    Details
  • Romantic farm in the Sienese hills
    From $238 per night (USD)

    VRBO

    Romantic farm in the Sienese hills

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    "Podere Poggiolo" is located on a green Tuscan hill on which it "rests" and to which it therefore owes its name. It is j ...

    From $238 per night (USD)

    VRBO

    Details
  • Small town Tuscan living at Casa Delle Campane
    From $180 per night (USD)

    Expedia

    Small town Tuscan living at Casa Delle Campane

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Situated in the charming and historic city center of Chiusi, Casa Delle Campane is the perfect location to experience sm ...

    From $180 per night (USD)

    Expedia

    Details
  • MONTEPULCIANO TUSCANY HOUSE 5 PLACES - 2 BATHROOMS - PARKING SPACE
    From $287 per night (USD)

    VRBO

    MONTEPULCIANO TUSCANY HOUSE 5 PLACES - 2 BATHROOMS - PARKING SPACE

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Tuscan-style villa, very close to the historic center of Montepulciano within walking distance. Arranged on the mezzanin ...

    From $287 per night (USD)

    VRBO

    Details
  • Iperbole country house, between Pienza and Montepulciano
    From $1966 per night (USD)

    Expedia

    Iperbole country house, between Pienza and Montepulciano

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    9

    The house sleeps comfortably 9 people in 4 double bedrooms and 1 single ( full bed) , each with its own bathroom. .The ...

    From $1966 per night (USD)

    Expedia

    Details
  • Beautiful studio located in a park with private garden, swimming pool, parking
    From $211 per night (USD)

    VRBO

    Beautiful studio located in a park with private garden, swimming pool, parking

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The small house, called 'La Limonaia' is located within a beautiful park of a holiday home in the historic center of Sin ...

    From $211 per night (USD)

    VRBO

    Details
  • Tuscan country house private fenced pool- garden- ideal for families
    From $527 per night (USD)

    VRBO

    Tuscan country house private fenced pool- garden- ideal for families

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    The structure consists of two independent living units but, if necessary, can be communicating to allow even groups of f ...

    From $527 per night (USD)

    VRBO

    Details
  • Casa Elia 6, Emma Villas
    From $743 per night (USD)

    VRBO

    Casa Elia 6, Emma Villas

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $743 per night (USD)

    VRBO

    Details
  • Farmhouse Le Stringaie
    From $395 per night (USD)

    VRBO

    Farmhouse Le Stringaie

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    The Le Stringaie farmhouse is an oasis of quiet and serenity in the green heart of Tuscany. We are in Val di Chiana, in ...

    From $395 per night (USD)

    VRBO

    Details
  • Margherita - San Giovanni farmhouse
    From $150 per night (USD)

    VRBO

    Margherita - San Giovanni farmhouse

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    The family-run farmhouse maintains what is the spirit of this type of holiday where, if you wish, you can attend normal ...

    From $150 per night (USD)

    VRBO

    Details
  • Apartment in Farmhouse-House with character
    From $174 per night (USD)

    VRBO

    Apartment in Farmhouse-House with character

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The beautiful 13th-century stone farmhouse is set on a knoll just 2km from the picturesque medieval hilltown of Cetona ( ...

    From $174 per night (USD)

    VRBO

    Details
  • Podere Osteria, Pienza, Siena and Chianti
    From $337 per night (USD)

    VRBO

    Podere Osteria, Pienza, Siena and Chianti

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Podere Osteria is a spacious holiday home in the picturesque Val d’Orcia, a UNESCO World Heritage landscape. This farmho ...

    From $337 per night (USD)

    VRBO

    Details
  • The House Annavittoria / garden in the village of Monticchiello
    From $238 per night (USD)

    VRBO

    The House Annavittoria / garden in the village of Monticchiello

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    The house, built on an old structure and recently restored, is located in the heart of Monticchiello, in the highest pos ...

    From $238 per night (USD)

    VRBO

    Details
  • Suite room in farmhouse with swimming pool surrounded by nature
    From $255 per night (USD)

    VRBO

    Suite room in farmhouse with swimming pool surrounded by nature

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located on the first floor of the farmhouse, Lunaspicchio has an area of 47sqm and is divided into two areas, day and ni ...

    From $255 per night (USD)

    VRBO

    Details
  • Suite room in farmhouse with swimming pool surrounded by nature
    From $255 per night (USD)

    VRBO

    Suite room in farmhouse with swimming pool surrounded by nature

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Solevante Suite The garden leads to Solevante, characterized by a large living area located outdoors, under a romantic p ...

    From $255 per night (USD)

    VRBO

    Details
  • Apartment in Farmhouse
    From $183 per night (USD)

    VRBO

    Apartment in Farmhouse

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Surrounded by vineyards growing grapes for the famous local wines, Vino Nobile di Montepulciano and Rosso di Montepulcia ...

    From $183 per night (USD)

    VRBO

    Details
  • Magnificent 2 Bedroom Apartment with Terrace and Air Conditioning
    From $382 per night (USD)

    Expedia

    Magnificent 2 Bedroom Apartment with Terrace and Air Conditioning

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Our apartment with Air Conditioning is located at the beginning and lower part of the Historical Center of Montepulciano ...

    From $382 per night (USD)

    Expedia

    Details
  • Apartment in Torrita, ground floor, terrace, swimming pool, Wi Fi, up to 4 pers
    From $116 per night (USD)

    VRBO

    Apartment in Torrita, ground floor, terrace, swimming pool, Wi Fi, up to 4 pers

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This apartment (37 sqm) is on the ground floor. It consists of a living room with a kitchenette (induction hob, fridge, ...

    From $116 per night (USD)

    VRBO

    Details
  • Lovely apartment in Montepulciano countryside, wine tours, bike tours, relax
    From $137 per night (USD)

    Expedia

    Lovely apartment in Montepulciano countryside, wine tours, bike tours, relax

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This is the ideal place for people to relax around the swimming pool. the apartment is equipped with a private bathroom ...

    From $137 per night (USD)

    Expedia

    Details
  • Montepulciano Lovely apartment in tuscany farmhouse with swimming pool, Wifi.
    From $155 per night (USD)

    VRBO

    Montepulciano Lovely apartment in tuscany farmhouse with swimming pool, Wifi.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Ideal place for unforgettable holidays among friends and family in Tuscany, between vineyards and olive groves and field ...

    From $155 per night (USD)

    VRBO

    Details
  • Poggio Cantarello Country Home
    From $183 per night (USD)

    VRBO

    Poggio Cantarello Country Home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located in Chiusi’s countryside, Poggio Cantarello is in a completely refurbished historic building. Set in its own spac ...

    From $183 per night (USD)

    VRBO

    Details
  • B&B Casalmustia - Room
    From $101 per night (USD)

    VRBO

    B&B Casalmustia - Room

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Locanda di Casalmustia is located in the ancient medieval tower, a small village located in the heart of Tuscany. Th ...

    From $101 per night (USD)

    VRBO

    Details
  • Luxury Tuscan Villa in Val d'Orcia, visit Montepulciano, Pienza and hot Springs!
    From $697 per night (USD)

    Expedia

    Luxury Tuscan Villa in Val d'Orcia, visit Montepulciano, Pienza and hot Springs!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    La Vittoria 10 is a traditional Tuscan Country Villa surrounded by greenery, forests and our olives grove. Strategic l ...

    From $697 per night (USD)

    Expedia

    Details
  • Villa Mulinello, secluded, panoramic view over Montepulciano valley.
    From $250 per night (USD)

    VRBO

    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 $250 per night (USD)

    VRBO

    Details
  • Villa Banditello, secluded, panoramic view over Montepulciano valley.
    From $280 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 $280 per night (USD)

    Expedia

    Details
  • Podere Bagnolo 8, Emma Villas
    From $790 per night (USD)

    VRBO

    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 $790 per night (USD)

    VRBO

    Details
  • Il Poggio dell'Eremita
    From $182 per night (USD)

    Expedia

    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 $182 per night (USD)

    Expedia

    Details
  • Stunning and Enormous 3 Bedroom Apt. in Historical Center of Montepulciano
    From $474 per night (USD)

    VRBO

    Stunning and Enormous 3 Bedroom Apt. in Historical Center of Montepulciano

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Apartment is located at beginning of the Historical Center of the town, and inside a Former Palace. It has been lovingly ...

    From $474 per night (USD)

    VRBO

    Details
  • Your home in Trequanda
    From $131 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 $131 per night (USD)

    Expedia

    Details
  • INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
    From $484 per night (USD)

    VRBO

    INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Casina Pellegrino - Tuscan Villa. A charming three tier house nestled in the sun kissed hills of Montepulciano, Italy. E ...

    From $484 per night (USD)

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    Details
  • Podere Gragnano 12, Emma Villas
    From $1370 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 $1370 per night (USD)

    Expedia

    Details
  • Villa in Trequanda with 5 bedrooms sleeps 10
    From $565 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 $565 per night (USD)

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    Details
  • Podere Collelungo 14, Emma Villas
    From $1423 per night (USD)

    Expedia

    Podere Collelungo 14, Emma Villas

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

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

    From $1423 per night (USD)

    Expedia

    Details
  • Podere Le Pozze
    From $1303 per night (USD)

    VRBO

    Podere Le Pozze

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    14

    The Podere le Pozze residence was the typical Tuscan rural farmhouse with all its austerity and charm. The animal stable ...

    From $1303 per night (USD)

    VRBO

    Details
  • LA VINOVA Ancient House Walking Distance - A/C,  Private Patio & Panorama
    From $215 per night (USD)

    Expedia

    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 at your exclusive disposal, with Wi-Fi and private patio with wide view on the ...

    From $215 per night (USD)

    Expedia

    Details
  • La casa delle Querce - Policiano suite
    From $255 per night (USD)

    VRBO

    La casa delle Querce - Policiano suite

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    <p>A short distance from birdwatching, cycling, and more, this pet-friendly apartment lets you experience it all. Thanks ...

    From $255 per night (USD)

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    Details
  • The house of the oaks - Poggino
    From $164 per night (USD)

    VRBO

    The house of the oaks - Poggino

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>A short distance from birdwatching, cycling, and more, this pet-friendly apartment lets you experience it all. Val di ...

    From $164 per night (USD)

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    Details
  • The house of the oaks - The Hague
    From $189 per night (USD)

    VRBO

    The house of the oaks - The Hague

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    <p>A short distance from birdwatching, cycling, and more, this pet-friendly apartment lets you experience it all. Thanks ...

    From $189 per night (USD)

    VRBO

    Details
  • Beatrice - Charming accommodation in period farmhouse near Montepulciano
    From $278 per night (USD)

    Expedia

    Beatrice - Charming accommodation in period farmhouse near Montepulciano

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beatrice is a splendid 5-seater residence inside Podere La Cava. It is spread over three floors and includes a large din ...

    From $278 per night (USD)

    Expedia

    Details
  • Beautiful characteristic apartment with private garden, pool and parking
    From $397 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 $397 per night (USD)

    VRBO

    Details
  • Residence Laura-Charming accommodation for 4 people in a farmhouse near Montepulciano
    From $225 per night (USD)

    Expedia

    Residence Laura-Charming accommodation for 4 people in a farmhouse near Montepulciano

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Laura is a fantastic 4-seat residence in the Podere La Cava. Spread over two floors, it includes a large tavern with a f ...

    From $225 per night (USD)

    Expedia

    Details
  • Wonderful private villa for 11 people with WIFI, TV, balcony and pets allowed
    From $149 per night (USD)

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    11

    Property Summary Nestled in the heart of Tuscany, Italy, Podere Casina is a charming detached farmhouse situated just 6 ...

    From $149 per night (USD)

    VRBO

    Details
  • The House of Oaks - Belvedere
    From $149 per night (USD)

    VRBO

    The House of Oaks - Belvedere

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    <p>Close to birdwatching, cycling, and more, this pet-friendly apartment brings it all within reach. Thanks to the conve ...

    From $149 per night (USD)

    VRBO

    Details
  • Apartment With View - Right in City Center
    From $173 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 $173 per night (USD)

    VRBO

    Details
  • Casa Girolamo - Super Central with Private Parking
    From $186 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 $186 per night (USD)

    Expedia

    Details
  • in the south of Tuscany between wines and Sienese hills
    From $119 per night (USD)

    VRBO

    in the south of Tuscany between wines and Sienese hills

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    The farmhouse has been renovated this year, is composed of two independent units but, if necessary, communicating to all ...

    From $119 per night (USD)

    VRBO

    Details
  • Authentic Tuscan Villa with infinity pool & stunning views of Val d'Orcia
    From $1564 per night (USD)

    Expedia

    Authentic Tuscan Villa with infinity pool & stunning views of Val d'Orcia

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Discover this beautiful Villa in the heart of Tuscany , just outside the charming village of Montefollonico . Tastefully ...

    From $1564 per night (USD)

    Expedia

    Details
  • Villa Borgo
    From $1826 per night (USD)

    VRBO

    Villa Borgo

    Bedrooms:
    8
    Bathrooms:
    7
    Sleeps:
    16

    <p>Located in the mountains, this welcoming vacation home lets you experience it all in Sarteano. Val di Chiana is just ...

    From $1826 per night (USD)

    VRBO

    Details
  • Luxury Privacy in the Heart of Tuscany
    Click For Pricing

    Expedia

    Luxury Privacy in the Heart of Tuscany

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    <p>While you're here, you can enjoy all the comforts of home and more, including a seasonal outdoor pool and a full-size ...

    Click For Pricing

    Expedia

    Details
  • Villa in Val D'orcia with panoramic whirlpool tub
    From $1691 per night (USD)

    VRBO

    Villa in Val D'orcia with panoramic whirlpool tub

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    15

    Going along a cypress avenue, you will come across "Casa Baccano Panoramica", a structure of about 400 square meters wit ...

    From $1691 per night (USD)

    VRBO

    Details
  • The House of Oaks - Pratino
    From $150 per night (USD)

    VRBO

    The House of Oaks - Pratino

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    <p>Close to birdwatching, cycling, and more, this pet-friendly apartment brings it all within reach. Thanks to the conve ...

    From $150 per night (USD)

    VRBO

    Details
  • Historical Guest House in the heart of Montepulciano. Family run.
    From $1588 per night (USD)

    VRBO

    Historical Guest House in the heart of Montepulciano. Family run.

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    <p>Nestled in Montepulciano, this 4-bedroom, 4-bathroom apartment brings it all within your reach. Fans of nature and th ...

    From $1588 per night (USD)

    VRBO

    Details
  • Four Seasons Thermae - Apartment Piazza Italia - Entire Accommodation
    From $161 per night (USD)

    VRBO

    Four Seasons Thermae - Apartment Piazza Italia - Entire Accommodation

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cozy and comfortable apartment of 105 m2 plus balcony, to spend holidays with the family or for couples. Central, near t ...

    From $161 per night (USD)

    VRBO

    Details
  • The House of Oaks - Rustic
    From $123 per night (USD)

    VRBO

    The House of Oaks - Rustic

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p>Close to birdwatching, cycling, and more, this pet-friendly apartment brings it all within reach. Val di Chiana is ju ...

    From $123 per night (USD)

    VRBO

    Details
  • Villa con Piscina Privata Immersa Nella Campagna Toscana
    From $1445 per night (USD)

    VRBO

    Villa con Piscina Privata Immersa Nella Campagna Toscana

    Bedrooms:
    9
    Bathrooms:
    6
    Sleeps:
    15

    <p>Close to cycling, winery tours, and more, this pet-friendly vacation home brings it all within reach. Thanks to the c ...

    From $1445 per night (USD)

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    Details
  • William Stuart  apartment
    From $136 per night (USD)

    VRBO

    William Stuart apartment

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Located on the piano nobile of the palace, this apartment is an oasis of light and tranquillity. The large windows of th ...

    From $136 per night (USD)

    VRBO

    Details
  • A very comfortable apartment in Tuscan style
    From $184 per night (USD)

    Expedia

    A very comfortable apartment in Tuscan style

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    The apartment named "Pienza" in Monticchiello is located on the first floor of Villa PoliFlora, with an exclusive view o ...

    From $184 per night (USD)

    Expedia

    Details
  • The house in the village - Angelica apartment - Vald'Orcia
    From $135 per night (USD)

    VRBO

    The house in the village - Angelica apartment - Vald'Orcia

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The house is located in the small medieval village of Monticchiello, within the imposing city walls. Immersed in the cla ...

    From $135 per night (USD)

    VRBO

    Details
  • Ann Kemp apartment
    From $153 per night (USD)

    Expedia

    Ann Kemp apartment

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    I have decided to dedicate this flat to my great-great-grandmother Ann Kemp.   is a spacious apartment featuring tradit ...

    From $153 per night (USD)

    Expedia

    Details
  • The Casa delle Querce - Tavernetto
    From $124 per night (USD)

    VRBO

    The Casa delle Querce - Tavernetto

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p>A short distance from birdwatching, cycling, and more, this pet-friendly apartment lets you experience it all. Thanks ...

    From $124 per night (USD)

    VRBO

    Details
  • Amazing view 3 bdr villa with pool & A/C in Pienza | Leccino
    From $631 per night (USD)

    Expedia

    Amazing view 3 bdr villa with pool & A/C in Pienza | Leccino

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Laundry facilities and a garden are available at this smoke-free farm stay. Air-conditioned accommodations at this farm ...

    From $631 per night (USD)

    Expedia

    Details
  • Unique view 3 bdr villa with pool & A/C in Pienza | Oriolo
    From $541 per night (USD)

    VRBO

    Unique view 3 bdr villa with pool & A/C in Pienza | Oriolo

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    <p>Located in Pienza, this welcoming vacation home lets you experience it all. Thanks to the convenient onsite parking, ...

    From $541 per night (USD)

    VRBO

    Details
  • Cozy retreat for 2 with pool & A/C in Val d'Orcia | Moraiolo
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    Expedia

    Cozy retreat for 2 with pool & A/C in Val d'Orcia | Moraiolo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This smoke-free farm stay features laundry facilities. Air-conditioned accommodations at this farm stay offer hair drye ...

    Click For Pricing

    Expedia

    Details
  • Casale Etruria In Chianciano Terme, Tuscany
    From $378 per night (USD)

    VRBO

    Casale Etruria In Chianciano Terme, Tuscany

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Property for exclusive use This residence was in the past one of the beautiful farmhouses scattered throughout the Tusca ...

    From $378 per night (USD)

    VRBO

    Details
  • Charming and Cozy Cottage in Tuscany! Visit Montepulciano Pienza, Cortona, Siena
    From $371 per night (USD)

    Expedia

    Charming and Cozy Cottage in Tuscany! Visit Montepulciano Pienza, Cortona, Siena

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Charming Cottage immersed in greenery, with private entrance, kitchen, large double bedroom, amazing bathroom with doubl ...

    From $371 per night (USD)

    Expedia

    Details
  • TWO PRIVATE VILLAS WITH 2 HEATED SWIMMING POOLS IN LUSH PRIVATE ESTATE SLEEPS 12
    From $820 per night (USD)

    VRBO

    TWO PRIVATE VILLAS WITH 2 HEATED SWIMMING POOLS IN LUSH PRIVATE ESTATE SLEEPS 12

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    Casa Febea and Casa delle Farfalle consists of 2 Villas adjacent to each other. The first Villa is composed of 3 double ...

    From $820 per night (USD)

    VRBO

    Details
  • Experience the Magic of Tuscany in a Private Estate of Three Luxury Villas
    From $1888 per night (USD)

    Expedia

    Experience the Magic of Tuscany in a Private Estate of Three Luxury Villas

    Bedrooms:
    18
    Bathrooms:
    18
    Sleeps:
    36

    Hidden among rolling olive groves and centuries-old trees on the border of Tuscany and Umbria, Villa Febea Estate is an ...

    From $1888 per night (USD)

    Expedia

    Details
  • Alloro - Zampugna Estate
    From $431 per night (USD)

    VRBO

    Alloro - Zampugna Estate

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Alloro Alloro is a 4 people apartment located in Zampugna Estate (5 apartments Agriturismo). This cute apartment is set ...

    From $431 per night (USD)

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    Details
  • Stunning Refurbished Farmhouse With All Luxury Amenities & Staff Included
    From $4597 per night (USD)

    VRBO

    Stunning Refurbished Farmhouse With All Luxury Amenities & Staff Included

    Bedrooms:
    9
    Bathrooms:
    9
    Sleeps:
    18

    This beautifully restored villa sits in an ideal location in the hills outside of Pienza in the famed, world heritage pr ...

    From $4597 per night (USD)

    VRBO

    Details