Vacation Rentals & Villas in Montepulciano

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54 Houses

Villa degli Olivi

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Private outdoor pool (unheated)

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Price per night from

$906

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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), Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$717

Villa Incanto

Bivio di San Biagio villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 15

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

1 of 2 filters match

Price per night from

$730

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), Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$861

Podere Monti

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

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

1 of 2 filters match

Price per night from

$1,340

Apartments in Residence

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$1,218

Il Grillo 10, Emma Villas

Acquaviva di Montepulciano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$762

Il Molinaccio 14+2, Emma Villas

Cervognano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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

1 of 2 filters match

Price per night from

$999

Bossoncina 8&1, Emma Villas

Montepulciano villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 9

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

1 of 2 filters match

Price per night from

$601

Podere Pisinano 8+2, Emma Villas

Montepulciano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$784

THE POGGIARONE

Montepulciano villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

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

1 of 2 filters match

Price per night from

$256

PODERE SAN BONO

Montepulciano villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

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

1 of 2 filters match

Price per night from

$220

Villa Ardita

Bivio di San Biagio house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 53 minutes

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

1 of 2 filters match

Price per night from

$986

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), Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$731

Charming Cottage in Peaceful Country Setting - Sleeps 6

Gracciano cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$232

Charming Cottage in Peaceful country Setting - Sleeps 2-4

Gracciano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$165

Charming Cottage in Peaceful Country Setting - Sleeps 2

Gracciano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

1 of 2 filters match

Price per night from

$110

Il Casale Di Manuele 12, Emma Villas

Cervognano villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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

1 of 2 filters match

Price per night from

$840

Podere San Buono 6, Emma Villas

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$622

Le Terre Di Nunzio 12

Bivio di San Biagio villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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

1 of 2 filters match

Price per night from

$1,135

CASA CERVOGNANO

Sant'Albino villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$222

Cerretini

Valiano villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$153

Tuscany Villa PODERE MONTI

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

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

1 of 2 filters match

Price per night from

$1,375

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: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$723

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: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$745

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

Montepulciano villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 16

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

1 of 2 filters match

Price per night from

$723

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: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$745

Casale Dei 12, Emma Villas

Cervognano villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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

1 of 2 filters match

Price per night from

$846

The Molinaccio 3

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$549

VILLA SILVIA

Sant'Albino villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 19

Responds fast! avg. 2 hours 23 minutes

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

1 of 2 filters match

Price per night from

$890

The Molinaccio 7

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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

1 of 2 filters match

Price per night from

$1,097

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: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$793

TASKO

Montepulciano villa

  • 5 bedrooms
  • 9 bathrooms
  • sleeps 9

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

1 of 2 filters match

Price per night from

$1,218

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: Private outdoor pool (heated), Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$793

Tenuta Senese Tenuta Senese

Montepulciano house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$637

Villa Ardene

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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

1 of 2 filters match

Price per night from

$854

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

1 of 2 filters match

Price per night from

$1,097

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rentals in Montepulciano

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