Vacation Rentals & Villas in Montalcino

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68 Houses

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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$904

La Capannina La Capannina

San Giovanni d'Asso house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

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$322

Olivella Olivella

San Giovanni d'Asso house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

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$737

Villa San Giovanni Villa San Giovanni

San Giovanni d'Asso villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 14

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$839

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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$723

Superb villa with pool 30 minutes from Siena and Montalcino

Montalcino villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 7

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$629

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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$358

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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$904

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

$863

Monterzi 4, Emma Villas

Montalcino villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$280

Great rentals within 20 miles that match your search

Stones of the ancient village

San Lorenzo a Merse house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$130

Poggio alla Rocca - SUN

Casale di Pari house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$617

Studio "Borghetto" at The House of the Oaks - Montepulciano

Montepulciano studio

  • Studio
  • 1 bathroom
  • sleeps 2

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$129

Casa di roberto

Siena b&b

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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$68

Charming Country Villa with Panoramic Private Pool

San Casciano dei Bagni villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$333

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$185

Casa Oliveto

Castelmuzio house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$704

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$172

Poggio Etrusco: Tuscan B&B, apts, & Cooking School

Montepulciano villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

“Beyond adjectives” There is no way to describe our stay here! Pamela and Johnny were more than welcoming. We arrived with our 7 & 4 year olds in tow...and from The gate greeting, we felt as if we were at "memee's house". Each kid had a job...gate keeping and keeping track of the red fetch toy for Bella. We had an unwarranted snafu on credit card deposits in Rome the day before...but it was of no concern to these wonderful and true hosts... Each morning, The breakfast was true to Tuscany yet appealing to the kids... we were within an hours drive of each of our potential destinations...and each evening with a game of fetch watching Bella and the kids...the hosts helped us decide upon on the next days itinerary! We will be back with the whole family in July!

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$1,048

Apartment "The Hague" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$209

Siena San Fabiano climatized villa with outdoor heated pool

Monteroni d'Arbia villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

“Perfect combo of charm, location & comfort in glorious Tuscany!” We first dicovered San Fabiano in summer 2003 and have made it a point to return with family and friends as often as we can ever since! The location is ideal for exploring Siena, all the hill towns of southern tuscany, the Chianti and even great for easy day trips to Florence. Besides the charm of this renovated farmhouse - it also has modenr comforts like ac, screened windows, kitchenettes in all the rooms and wireless internet - plus a swimming pool! We love walking into the little town of Monteroni for our morning cappucinos and hiking the trails around this lovely farm estate. Great for kids and family gatherings as well as couples. We get through New England winters by dreaming of returning to San Fabiano. Highly recommended!

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Price per night from

$1,233

TASKO

Montepulciano villa

  • 5 bedrooms
  • 9 bathrooms
  • sleeps 9

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$1,233

Borgo Castelrotto, pool villa 18 guests at Castelnuovo Tancredi Estate

Buonconvento farmhouse

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 20

Responds fast! avg. 1 hour 59 minutes

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$1,726

Villa with private pool, air conditioning, quiet area & nice views 3km from town

Chianciano Terme villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 21 minutes

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$359

Villa Castelnuovo Tancredi - The perfect Tuscan Experience

Buonconvento farmhouse

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 22

Responds fast! avg. 1 hour 59 minutes

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$5,810

Stunning Tuscan views from traditional farmhouse 10mins to downtown Siena

Costalpino villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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$307

Exclusive luxury villa in the Tuscan countryside. 14 rooms, pool, A/C and Wi-Fi!

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

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$3,599

Farmhouse Santa Maria - Grandpa's House

Montefollonico farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 29 minutes

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$74

Country house (6 + 2) with swimming pool in an enchanting landscape

Lucignano farmhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 31 minutes

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$146

Casa Dei Ro.Gi. - Montepulciano - Tuscany

Abbadia di Montepulciano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

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$79

Apartment "Belvedere" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$172

Podere Isabella, the pearl of Val d'Orcia

Monticchiello villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 20

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$1,233

The Source The Source

Chianciano Terme apartment

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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$746

Mulino Mulino

Lucignano apartment

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

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$675

Belguardo BELGUARD 1

Chianciano Terme apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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$337

Belguardo BELGUARDO 2

Chianciano Terme house

  • 11 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$505

Ambassador Ambassador

Vivo d'Orcia house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$249

Monteori Monteori

Chianciano Terme apartment

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$893

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