Vacation Rentals & Villas in Montepulciano

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55 Houses

Villa degli Olivi

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Heated pool Private outdoor pool (unheated)

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Price per night from

$912

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Villa Incanto

Bivio di San Biagio villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 15

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$735

Villa Boschetto - Stunning villa with garden and pool near Montepulciano

Bivio di San Biagio villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 of 2 match: Private outdoor pool (unheated), Heated pool

1 of 2 filters match

Price per night from

$722

Villa Montepulciano - Magnificent villa with garden and pool in Val d'Orcia area

Bivio di San Biagio villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

1 of 2 match: Private outdoor pool (unheated), Heated pool

1 of 2 filters match

Price per night from

$867

Podere Monti

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,350

Apartments in Residence

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

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Fattoria San Martino

Montepulciano b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,228

Podere Pisinano 8+2, Emma Villas

Montepulciano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$789

Il Molinaccio 14+2, Emma Villas

Cervognano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,005

Bossoncina 8&1, Emma Villas

Montepulciano villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 9

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$605

Il Grillo 10, Emma Villas

Acquaviva di Montepulciano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$769

Villa Ardita

Bivio di San Biagio house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$993

THE POGGIARONE

Montepulciano villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$258

PODERE SAN BONO

Montepulciano villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$221

Charming Cottage in Peaceful Country Setting - Sleeps 6

Gracciano cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$234

Charming Cottage in Peaceful country Setting - Sleeps 2-4

Gracciano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$166

Charming Cottage in Peaceful Country Setting - Sleeps 2

Gracciano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$111

Le Terre Di Nunzio 12

Bivio di San Biagio villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,143

Il Casale Di Manuele 12, Emma Villas

Cervognano villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$846

Podere San Buono 6, Emma Villas

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$626

CASA CERVOGNANO

Sant'Albino villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$224

Cerretini

Valiano villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$154

16 persons with 8 bedrooms, private pool and WiFi. Only 2 km to Montepulciano!

Montepulciano villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 16

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$729

The Molinaccio 7

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,105

The Molinaccio 3

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$553

San Biagio, private house with pool and A/C just 900 meters to Montepulciano!

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$751

Villa with 8 bedrooms near Montepulciano. Private pool and large gardens!

Montepulciano villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 16

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$729

Independent villa with private pool, hot tub, WI-FI, A / C near Montepulciano!

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$751

Casale Dei 12, Emma Villas

Cervognano villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$852

Tuscany Villa PODERE MONTI

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,386

VILLA SILVIA

Sant'Albino villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 19

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$896

Villa LA VALIANA (Montepulciano)

Montepulciano villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Paradise in Tuscany!” This lovely villa has it all and is the kind of place that makes you want to stay and 'while away' the afternoon among its many outdoor spaces: whether it's dining in the gazebo overlooking the vineyard, watching as the evening sun sets over the gently rolling hills, relaxing in a chaise by the glistening pool, enjoying a café crème or glass of wine on the patio surrounded by roses, lemon trees and pots of flowers, or gazing beyond at Cortona high on a hill or Trasimeno Lake in the valley below, you will come to know this is a very special place. La Valiana is centrally located for explorations to nearby villages and wineries, Cortona, lovely Pienza (a favorite), Montepulciano or easy day trips to Montalcino, Orvieto, Siena, Arezzo, Florence, Chianti and beyond. It is comfortable and beautifully decorated in classic, Tuscan style with fine architectural details such as wrought iron arched windows, doors and Travertine marble floors. You will be well taken care of and looked after by Cecelia and her Family who are the most gracious hosts - they are dedicated to making your stay a wonderful, memorable one, making themselves available should you need any assistance. Their warm hospitality and attention to detail will make you feel special and, at once, a part of the family. If you opt to have a meal prepared and waiting for your arrival after a long day of travel or touring, it will not disappoint and, quite possibly, could be one of the best meals in all of Tuscany, especially when enjoyed under the stars. You will want for nothing - except perhaps to extend your stay, or at the very least, come back again! You can be sure we will be back!!

1 of 2 match: Private outdoor pool (unheated), Heated pool

1 of 2 filters match

Price per night from

$737

Walk to Town! Luxury Villa in Montepulciano, Tuscany w/ Pool & Spa!!

Montepulciano villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 58 minutes

1 of 2 match: Private outdoor pool (unheated), Heated pool

1 of 2 filters match

Price per night from

$1,031

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

Sant'Albino villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 21

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$799

TASKO

Montepulciano villa

  • 5 bedrooms
  • 9 bathrooms
  • sleeps 9

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,228

Podere Sant'Albino private villa with pool and A/C. Walking distance to a town!

Sant'Albino villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$799

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,105

Tenuta Senese Tenuta Senese

Montepulciano house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

1 of 2 match: Heated pool, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$642

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