Vacation Rentals & Villas in Montepulciano

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161 Houses

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!!

Match: Fridge Private outdoor pool (heated)

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Price per night from

$738

Villa degli Olivi

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Fridge Private outdoor pool (heated)

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Price per night from

$916

Villa Boschetto - Stunning villa with garden and pool near Montepulciano

Bivio di San Biagio villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Fridge Private outdoor pool (heated)

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Price per night from

$725

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: Fridge Private outdoor pool (heated)

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Price per night from

$870

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Depadance il Girasole

Montepulciano farmhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

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

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Price per night from

$308

Tarugi palace residence

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$185

Apartment Montepulciano Stazione (Siena)

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Country House at Antico Podere in Montepulciano, Tuscany

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$148

Siena Historic Center Stylish Flat with Balcony!

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$137

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), Fridge

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Price per night from

$222

MONTEPULCIANO OLD TOWN

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$104

I Tetti Sulla Valle - nel cuore di Montepulciano

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$111

Little Brick House on Siena Hills with Balconies

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

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Price per night from

$106

relax in the countryside with swimming pool

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$117

apartment in Montefollonico

Montepulciano apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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

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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), Fridge

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Price per night from

$183

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), Fridge

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Price per night from

$455

Country villa in Montepulciano Tuscany

Montepulciano farmhouse

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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

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Price per night from

$184

Apartment with Little Arch

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

1 of 2 filters match

Price per night from

$113

STEFANIA TOWNHOUSE

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$160

I CASALI DI TOSCANA

Montepulciano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

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Price per night from

$369

Buen retiro

Abbadia di Montepulciano lodge

  • 8 bedrooms
  • 3 bathrooms
  • sleeps 7

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

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Price per night from

$246

Belguardo

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$86

MONTEPULCIANO TOWN HOUSE POG

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

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Apartments in Residence

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Farmhouse Le Gualtiere

Sant'Albino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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

1 of 2 filters match

Price per night from

$96

Il Grillo 10, Emma Villas

Acquaviva di Montepulciano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$770

Bossoncina 8&1, Emma Villas

Montepulciano villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 9

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

1 of 2 filters match

Price per night from

$606

Gues tHouse del Corso

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

1 of 2 filters match

Price per night from

$160

Charming 1-Bed Apartment in Montepulciano

Bivio di San Biagio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$198

Villa Poggio Fagianino

Sant'Albino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$357

Le Grazie 8

Sant'Albino villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$512

Le Colombelline 12, Emma Villas

Montepulciano villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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

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Price per night from

$1,106

Apartement for 2 ppl. with shared pool and terrace at Montepulciano

Cervognano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 50 minutes

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

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Price per night from

$202

Appartement for 2 ppl. with shared pool and terrace at Montepulciano

Cervognano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 50 minutes

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

1 of 2 filters match

Price per night from

$162

Il Molinaccio 14+2, Emma Villas

Cervognano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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

1 of 2 filters match

Price per night from

$1,010

Podere Pisinano 8+2, Emma Villas

Montepulciano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$793

Farmhouse Il Fienile

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$185

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rentals in Montepulciano

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