Vacation Rentals & Villas in Montepulciano

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179 Houses

Villa degli Olivi

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Non-Smoking property

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Price per night from

$917

Villa Boschetto - Stunning villa with garden and pool near Montepulciano

Bivio di San Biagio villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Non-Smoking property

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Price per night from

$726

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

Bivio di San Biagio villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

Match: Private outdoor pool (heated) Non-Smoking property

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Price per night from

$871

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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: Non-Smoking property, Private outdoor pool (heated)

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Price per night from

$741

STEFANIA TOWNHOUSE

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$161

Relais Ortaglia Voltaia Room

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$334

Relais Ortaglia Room San Donato

Montepulciano b&b

  • 1 bedroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$334

Relais Ortaglia Balcony Room

Montepulciano b&b

  • 1 bedroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$284

Relais Ortaglia Gracciano

Montepulciano b&b

  • 1 bedroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$247

Casa della Luna

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$99

I Tetti Sulla Valle - nel cuore di Montepulciano

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$111

4 bedrooms in a tower, home of a sculptor

Montepulciano b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$457

TASKO

Montepulciano villa

  • 5 bedrooms
  • 9 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$1,234

The Countess' Blue Suite

Montepulciano guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$198

MONTEPULCIANO OLD TOWN

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$104

Beautiful two bedroom Studio in Montepulciano

Bivio di San Biagio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$395

Appartamento con Mansarda 11 posti a Montepulciano Centro Storico

Montepulciano condo

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$223

Casa Bibi Montepulciano 5 places

Montepulciano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$186

Historic building in the center of Montepulciano

Montepulciano house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$457

Colombi Palace Montepulciano

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$145

Lovely home of Olimpia in Montepulciano, wifi, wine and bikes, music and termal

Montepulciano apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$124

Ostro Bed & Breakfast at Montepulciano in Tuscany

Montepulciano b&b

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$124

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

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$129

Borgo dei Sette Tigli #4

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect!” We had a 4-night stay here in early July of this year and had such a wonderful experience. We were greeted by alice who was very accommodating and patient even though we lost our way and were an hour late arriving. She was a sweet as can be and made sure we were settled and had all our questions answered before leaving. Barbara (the owner, I believe) came by the next day to greet us and was also wonderful, making sure that we were satisfied. She was taking care of details regarding her forthcoming nuptials which were to take place 5 days after our arrival. She was very accommodating and helpful even though she must have had lots on her mind. We rented a 2-bedroom, 2-bathroom apartment with a fully-equipped kitchen, living room/dining room, small walkout with table and chairs off of the kitchen. This was perfect for our family of 4 -- two adults and two teenage girls. The accommodations are superb: comfortable beds with great quality linens; recently and tastefully renovated rooms, spacious and inviting, fully equipped kitchen with dish washer and clothes washer; clothes are a quick dry in the summer sun on a dryer rack that is provided. The exterior of the buildings are very attractive, landscaping is detailed and well tended and there is a beautiful, beautiful pool. Now picture this in the middle of the lovely landscape of the Tuscany region. Need I say more? If you're thinking of staying here, don't hesitate, it is superb. Ideally located close to Montepulciano (5 minutes by car) and not far from the major highway (15 minutes tops) if you feel that you'll be doing some day trips. Exceptional value for the money. I highly recommend this vacation rental and only wish I could go back. Hopefully some day.

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$184

Agr. Sunflower double room depandance

Montepulciano farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$99

Depadance il Girasole

Montepulciano farmhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$309

Double room PANORAMIC VIEW

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$124

Double rooms with bathroom and Panoramic Terrace

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$148

L'ANTICO GRANAIO

Montepulciano cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$153

Relais Ortaglia Talosa Room

Montepulciano b&b

  • 1 bedroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$247

Buen retiro

Abbadia di Montepulciano lodge

  • 8 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$247

B&B Casale a Poggiano-The Best Breakfast in town

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

1 of 2 filters match

Price per night from

$105

B&B Casale a Poggiano-The top Breakfast in town

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$105

Tuscan Villa Argiano 1 room,Montepulciano, B&B

Montepulciano villa

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$81

Tuscany Villa in Argiano near Montepulciano B&B 1 Room, swimming pool, wifi

Montepulciano b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

1 of 2 filters match

Price per night from

$74

Montorio

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Podere Monti

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

1 of 2 filters match

Price per night from

$1,358

Podere Poggioalsole

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Non-Smoking property

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Price per night from

$173

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