Vacation Rentals & Villas in Montalcino

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585 Houses

Cozy Collection of Villas in Tuscany

Montalcino villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 26

“Great stay- we hope to return!” We truly enjoyed our stay here. Matteo was a wonderful host and even met us outside of town to make sure that we did not get lost on the way to the agriturismo. The room was clean and very comfortable, especially important since we brought our 3 month old baby. The kitchenette was very useful and had everything we needed. This was a perfect place to stay while in town for Benvenuto Brunello because it allowed us a gorgeous drive and was away from crowds. We even enjoyed Quercecchio's wine, both Brunello and Rosso. Next time, we hope to visit around harvest time!

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$1,695

Private villa with pool in the Montalcino area. 8 persons in 5 bedrooms!

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

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$900

Casal d'Asso

San Giovanni d'Asso house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 7

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Price per night from

$796

ART-HANGAR BY TUSCAN-EXPERIENCE

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$713

La Capannina La Capannina

San Giovanni d'Asso house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

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$321

Olivella Olivella

San Giovanni d'Asso house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

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$734

Alborata 10, Emma Villas

San Giovanni d'Asso villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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$722

Villa San Giovanni Villa San Giovanni

San Giovanni d'Asso villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 14

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$836

Pasqui Villas La Consuma :historic villa in a village ,pool, garden, view ,WiFi

San Giovanni d'Asso villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 14

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$720

TUSCAN FARMHOUSE NEAR MONTALCINO FOR FAMILIES

San Giovanni d'Asso farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$221

Casale San Giovanni

San Giovanni d'Asso farmhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$338

Casa Brunello di Montalcino

Montalcino apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$438

Farm House Bampton-Brunello

Val d'Orcia apartment

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

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$283

Pasqui Villas: La Capanna,country chic house in a village:garden,pool,view,WiFi

San Giovanni d'Asso villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

“Casa Lorenzo - A perfect slice of Tuscan heaven” I have stayed at this house multiple times in the past and our entire family adores the house and location. The owner is extremely nice and charming, her caretaker is magnificent, the grounds are beautiful and the amenities within an extremely short walk are sublime. The house is perfect for a family of 5 (of any age) or for two couples and it is absolutely charming. The airconditioning works well, the kitchen is nice and functional and the bedrooms and bathrooms are perfectly nice and comfortable. It has a small swimming pool to reduce the summer heat if you wish and a functional outdoor charcoal grille. The location cannot be beat. Don't miss the restaurant next door which is one of the best in southern Tuscany. The house is close to all that the Crete Senese offers and requires extremely short drives to visit Pienza, Montalcino, and Montepulciano. We could linger here for weeks and we would not complain at all.

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$356

Agriturismo La Buca

Val d'Orcia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$123

CASALE TOSCANO VIEWS OF CRETE SENESI AND VAL D'ORCIA

San Giovanni d'Asso farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$221

B&b l'incanto

Montalcino b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$83

Farm House Bampton-Red

Val d'Orcia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$246

Luxury villa near Montalcino with an unique view. 4 bedrooms with private pool!

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$900

Villa Molino

Montalcino villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$483

Hajar Montisi Siena

San Giovanni d'Asso house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Borgo La Bagnaia #Villa Sarageto

San Giovanni d'Asso villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 43 minutes

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Price per night from

$860

Monterzi 4, Emma Villas

Montalcino villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$279

Apartment in Montalcino ID 3530

Montalcino apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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$361

Villa Molino

Castelnuovo dell'Abate villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$799

Great rentals within 20 miles that match your search

Podere Monti, 7 bedrooms villa near Montepulciano. Private pool, A/C and Wi-Fi!

Sant'Albino villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 21

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Price per night from

$799

Stones of the ancient village

San Lorenzo a Merse house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$129

Giunia

San Lorenzo a Merse villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 27

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Price per night from

$2,725

Aiola

Sarteano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$1,654

Morgana

Buonconvento villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

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Price per night from

$1,699

DOWNTOWN WITH A VIEW!Entire Home w. huge Terraces

Montepulciano house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$280

FARM-HOUSE "PODERE OUTLETS" (APARTMENT "B")

Castel Del Piano house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$50

Villa Maria 3 piani (indipendente - garage)

Sinalunga house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$111

Agriturismo Podere Camollia - La Tinaia

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 19 minutes

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Price per night from

$154

Podere Camollia - "The Volticine"

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 19 minutes

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Price per night from

$117

The farm Sughereto

Roccastrada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$332

Appartamento Lavanda Villa Pennella

Monticchiello apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$199

Villa Pennella

Monticchiello house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$397

Viewing 38 of 585
rentals in Montalcino

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