Vacation Rentals & Villas in Montalcino

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244 Houses

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

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$901

Casal d'Asso

San Giovanni d'Asso house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated)

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Price per night from

$797

ART-HANGAR BY TUSCAN-EXPERIENCE

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$713

La Capannina La Capannina

San Giovanni d'Asso house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

Match: Private outdoor pool (unheated)

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Price per night from

$321

Olivella Olivella

San Giovanni d'Asso house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$735

Alborata 10, Emma Villas

San Giovanni d'Asso villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$725

Villa San Giovanni Villa San Giovanni

San Giovanni d'Asso villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$837

Above the stove, luxury villa with private pool

Montalcino villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

Match: Private outdoor pool (unheated)

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Price per night from

$923

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

San Giovanni d'Asso villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated)

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Price per night from

$722

Fonte Aulente Montalcino

Val d'Orcia farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Private outdoor pool (unheated)

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Price per night from

$111

Casale San Giovanni

San Giovanni d'Asso farmhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$338

Superb villa with pool 30 minutes from Siena and Montalcino

Montalcino villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated)

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Price per night from

$627

Scannelli Farm

Val d'Orcia b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$148

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.

Match: Private outdoor pool (unheated)

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Price per night from

$357

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

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$901

Casale Le Borghe (10 guests) - Montalcino, Tuscany

San Giovanni d'Asso villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$676

Borgo La Bagnaia #Villa Sarageto

San Giovanni d'Asso villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 43 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$861

Monterzi 4, Emma Villas

Montalcino villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$280

Splendida Villa con Piscina privata e SPA

Montalcino villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$1,168

Villa Molino

Castelnuovo dell'Abate villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$799

Great rentals within 20 miles that match your search

Old farmhouse in the Val d'Orcia

Sarteano house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$493

La Tana del Bianconiglio - App. Uva

Castiglione D'Orcia apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Match: Private outdoor pool (unheated)

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Price per night from

$197

The farm Sughereto

Roccastrada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$332

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

Sant'Albino villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 21

Match: Private outdoor pool (unheated)

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Price per night from

$800

Spider homes

Arcidosso farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$185

Agriturismo Gello - Villa with panoramic pool in Tuscany - Chianciano Terme

Chianciano Terme villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 22

Match: Private outdoor pool (unheated)

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Price per night from

$702

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$516

Villa Oliveto

Castelmuzio villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$669

Casa Oliveto

Castelmuzio house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$702

Match: Private outdoor pool (unheated)

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Price per night from

$183

Agriturismo L'Olivo

Serre di Rapolano cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Responds fast! avg. 1 hour 11 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$111

Poggio ai Gelsi

Pienza lodge

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$566

Agriturismo Villa Panorama - 8 posti letto - Villa esclusiva - Siena

Rigaiolo villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$590

Collosodo farmhouse with private pool

Monticchiello townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$240

luxury villa few steps from Pienza, outdoor-indoor swimming pool,air-conditoned

Pienza apartment

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 58 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,581

Enchanting country house (12 + 4) with private pool

Lucignano b&b

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$290

Responds fast! avg. 2 hours 58 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$775

Villa La Bifora

Sinalunga villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated)

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Price per night from

$775

Viewing 38 of 244
rentals in Montalcino

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