Vacation Rentals & Villas in Montepulciano

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150 Houses

VILLA CORTONA (SOFIA) 10 BEDROOMS

Fratticciola farmhouse

  • 13 bedrooms
  • 11 bathrooms
  • sleeps 20

Match: Private outdoor pool (heated) Safe

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Price per night from

$1,844

Villa for 6 ppl. with swimming-pool and garden at Osteria delle Noci

San Sigismondo villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 50 minutes

Match: Private outdoor pool (heated) Safe

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Price per night from

$194

Tus003 - Villa surrounded by rolling hills, Tuscany

Contignano condo

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 18

Match: Private outdoor pool (heated) Safe

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Price per night from

$2,723

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Villa Sarteano

Contignano villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

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

1 of 2 filters match

Price per night from

$1,950

CASA FEBEA 6 people

Chiusi villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$191

Luxury Villa Avorio

Chiusi villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 16

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

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Price per night from

$3,681

Luxury Villa Lunablu

Cetona villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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

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Price per night from

$1,932

Villa Antico Casale - Entire property exclusive 14 beds

Panicale villa

  • 14 bedrooms
  • 4 bathrooms
  • sleeps 14

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

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Price per night from

$678

Podere il Sogno

Tavernelle villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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

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Price per night from

$908

Romantic Cottage in Tuscany

Radicofani cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 11 minutes

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

1 of 2 filters match

Price per night from

$111

Villa del Lago - Homelike Villas

Castiglione del Lago villa

  • 19 bedrooms
  • 15 bathrooms
  • sleeps 45

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

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Price per night from

$1,212

Villa Glicine- Homelike Villas

Citta della Pieve villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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

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Price per night from

$329

Villa Alessandro - Homelike Villas

Citta della Pieve villa

  • 17 bedrooms
  • 9 bathrooms
  • sleeps 37

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

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Price per night from

$1,785

Villa D'Orcia - Homelike Villas

Castiglione D'Orcia villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 15

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

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Price per night from

$631

Villa Margherita- Homelike Villas

Fratticciola villa

  • 11 bedrooms
  • 10 bathrooms
  • sleeps 24

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

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Price per night from

$969

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

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Price per night from

$626

Villa Asciano 20 - Fantastic villa with garden and pool in Val d'Orcia

Montisi villa

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 20

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

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Price per night from

$2,164

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: Safe, Private outdoor pool (heated)

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Price per night from

$724

Villa Farneta - Elegant villa with private garden and pool near Cortona

Fratticciola villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 17

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

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Price per night from

$1,812

Villa Clemente - Lovely villa with private pool near Arezzo

Lucignano villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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

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Price per night from

$265

Villa Rosina - Villa with private pool and small gym near Arezzo

Lucignano villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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

1 of 2 filters match

Price per night from

$265

Villa Bianca - Homelike Villas

Piegaro villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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

1 of 2 filters match

Price per night from

$1,312

Villa la Fenice- Homelike Villas

Brolio house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 22

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

1 of 2 filters match

Price per night from

$721

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: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$869

Villa Ranciano - With private pool near Lake Trasimeno

Gioiella villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 18

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

1 of 2 filters match

Price per night from

$608

Villa Colombini - Superb villa with private garden and pool in Val d'Orcia

Trequanda villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

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

1 of 2 filters match

Price per night from

$507

Villa Asciano 30 - Stunning villa with garden and pool in Val d'Orcia

San Giovanni d'Asso villa

  • 14 bedrooms
  • 15 bathrooms
  • sleeps 30

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

1 of 2 filters match

Price per night from

$3,115

Villa Arianna - 3 bdr-villa over the Trasimeno Lake!

Cortona villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

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

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Price per night from

$1,022

Po' del Vento:è tutto intorno a te:16, piscina riscaldata, parco giochi, camino

Citta della Pieve guest house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

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

1 of 2 filters match

Price per night from

$1,106

Villa degli Olivi

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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

1 of 2 filters match

Price per night from

$915

Casale Etruria

Chianciano Terme house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$352

Amazing Villa Near The Lake With Pool

Cantagallina villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 32 minutes

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

1 of 2 filters match

Price per night from

$546

Cortona Charming - National Suite

Cortona b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

1 of 2 filters match

Price per night from

$198

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: Safe, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$738

Responds fast! avg. 2 hours 58 minutes

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

1 of 2 filters match

Price per night from

$1,757

Villa Miralaghi 8-9 WI-FI, Biliardo, Camino, Piscina riscaldata, Jacuzzi, Bocce

Citta della Pieve house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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

1 of 2 filters match

Price per night from

$1,106

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

1 of 2 filters match

Price per night from

$907

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

1 of 2 filters match

Price per night from

$907

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rentals in Montepulciano

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