Vacation Rentals & Villas in Montepulciano

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52 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: Private outdoor pool (heated) Secure parking

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Price per night from

$740

Villa degli Olivi

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Secure parking

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Price per night from

$916

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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: Secure parking, Private outdoor pool (heated)

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Price per night from

$724

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), Secure parking

1 of 2 filters match

Price per night from

$74

Tuscan Villa Argiano 1 room,Montepulciano, B&B

Montepulciano villa

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$81

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: Secure parking, Private outdoor pool (heated)

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Price per night from

$869

La Casina Toscana, central with parking and wi-fi

Montepulciano cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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

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Price per night from

$142

Tenuta di Argiano in Montepulciano, apartment, pool, wifi, winery, trekking

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$105

Emerald's Home Family

Acquaviva di Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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

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Price per night from

$148

Emerald's Home Elegance

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$98

BEAUTIFUL EMERALD'S HOME IN TUSCANY

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$370

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 (heated), Secure parking

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Price per night from

$1,031

Relais Ortaglia - Double Bedroom

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$235

Relais Ortaglia - Suite

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$309

Tenuta Senese Tenuta Senese

Montepulciano house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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

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Price per night from

$645

Gues tHouse del Corso

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

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Price per night from

$160

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), Secure parking

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Price per night from

$835

davide apartment Montepulciano

Bivio di San Biagio apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$117

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), Secure parking

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Price per night from

$802

Il Molinaccio di Montepulciano 1

Montepulciano farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$185

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), Secure parking

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Price per night from

$732

The Molinaccio 7

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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

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Price per night from

$1,110

The Molinaccio 3

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$555

Tigli #2, apt Montepulciano area for 5 persons with A/C, Wi-Fi and swimming pool

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful place with beautiful vistas of the hills and valley fr” We were able to stay 5 days and 4 nights in this lovely place. The property was as or better than described. Very comfortable and clean. Everything we needed for the time we stayed there. It was a very nice location to be able to take day trips to Siena, Pienza, Montepulciano, Montalcino and Orvieto on the way back to Rome. Such great views from apt #2. We even saw deer in the evening and morning running through the fields below. Montepulciano is very close and you can be there in a matter of a few minutes to shop at the Conard or enjoy shopping and meals. There are a lot of rules on lists provided to follow regarding trash, cleaning, linens, etc. We didn't see much of the caretakers as they had other jobs/work, a new baby, etc. But they were very pleasant and helpful if we needed anything. This is definitely a place we would go back to again.Once we found it. I am glad we got to the location during the day and not at night. You just really have to believe the directions and keep going. The signs are a bit small and I am glad everyone was looking for them. Please go eat at the 13 Gobbi in Montefollonico about 5-6 miles away on a hill top to the north. You will love it. And have their house wine, great. By the way, a bottle of wine and olive oil was provided upon our stay. Both were very good. Wish I could have bought more of it.

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

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Price per night from

$194

Tigli #5, flat near Montepulciano with 2 bedrooms. A/C, Wi-Fi and swimming pool

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Return visit” One again we enjoyed our visit to this well run set of apartments. They are ready on time, cleean and well equiped. A caretaker lives on site to provide backiup if needed. The gardena and pool are tell tended and maintained. Montipulciano is 10 mins away by car. Be aware that it is in the middle of the countryside with no shops or restaurants nearby.

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

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Price per night from

$173

Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool!

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“family reunion” we looked for a place where the whole family could celebrate a 70'years birthday. We were altogether 4 families of 8 adults and 7 children. The property was ideal for us. We occupied 5 apartments and had the whole place at our disposal. It was nice that we had the whole property at our own so that we should not consider other residents. All apartments were in good standard and the pool area was nice. We had really no complains at all. One evening a pizza evening was arranged by the manager and it was splendid. Further the surrounding towns were interesting and marvelous.

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

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Price per night from

$194

Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$151

B&B Casale a Poggiano-The best Breakfast and more

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

1 of 2 filters match

Price per night from

$105

Farmhouse Olimpia in Montepulciano, apartment furnished , pool, wifi

Acquaviva di Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

1 of 2 filters match

Price per night from

$111

Tenuta di Argiano in Montepulciano, apartment, winery, pool, wifi

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$105

Charming Cottage in Peaceful Country Setting - Sleeps 6

Gracciano cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$235

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), Secure parking

1 of 2 filters match

Price per night from

$754

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), Secure parking

1 of 2 filters match

Price per night from

$802

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), Secure parking

1 of 2 filters match

Price per night from

$732

il Molinaccio Montepulciano 3

Montepulciano farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$555

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

1 of 2 filters match

Price per night from

$1,110

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), Secure parking

1 of 2 filters match

Price per night from

$754

Villa Ardene

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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

1 of 2 filters match

Price per night from

$863

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