Vacation Rentals & Villas in Montepulciano

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113 Houses

Villa degli Olivi

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Pets allowed

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Price per night from

$826

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) Pets allowed

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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) Pets allowed

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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: Pets allowed, Private outdoor pool (heated)

1 of 2 filters match

Price per night from

$741

The Countess' Blue Suite

Montepulciano guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

1 of 2 filters match

Price per night from

$198

Historic building in the center of Montepulciano

Montepulciano house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$457

Tarugi palace residence

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$186

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), Pets allowed

1 of 2 filters match

Price per night from

$124

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), Pets allowed

1 of 2 filters match

Price per night from

$184

Farmhouse Le Gualtiere

Sant'Albino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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

1 of 2 filters match

Price per night from

$97

Le Colombelline 12, Emma Villas

Montepulciano villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

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

1 of 2 filters match

Price per night from

$1,071

Tuscany Villa in Montepulciano,Free Parking,Free Wi-fi,view of valley

Bivio di San Biagio villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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

1 of 2 filters match

Price per night from

$309

Foresteria Danesi Bellarmino

Montepulciano apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$161

Villa Incanto

Bivio di San Biagio villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 15

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

1 of 2 filters match

Price per night from

$755

Roofview in Montepulciano

Bivio di San Biagio apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$408

relax in the countryside with swimming pool

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

1 of 2 filters match

Price per night from

$118

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

Montepulciano studio

  • Studio
  • 1 bathroom
  • sleeps 2

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

1 of 2 filters match

Price per night from

$129

Burraia Luxury House

Montepulciano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$135

Casanova of the Woods

Montepulciano farmhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

1 of 2 filters match

Price per night from

$506

Holiday Resort in Montepulciano M,,air conditioning,swimmingpool,wine tasting

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 58 minutes

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

1 of 2 filters match

Price per night from

$142

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$185

"Policiano Suite" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$309

Apartment "The Hague" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

1 of 2 filters match

Price per night from

$209

Country villa in Montepulciano Tuscany

Montepulciano farmhouse

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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

1 of 2 filters match

Price per night from

$184

Farmhouse Il Palazzo dei Diavoli Montepulciano - Tuscany Val d 'Orcia

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$149

I Tigli, apt in farmhouse only 5 km to Montepulciano. 2 bedrooms, pool and Wi-Fi

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$194

Apartment La Loggia

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

1 of 2 filters match

Price per night from

$142

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$172

Il Grillo 10, Emma Villas

Acquaviva di Montepulciano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

1 of 2 filters match

Price per night from

$773

Bossoncina 8&1, Emma Villas

Montepulciano villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 9

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

1 of 2 filters match

Price per night from

$609

Flat with terrace,view,Wi-Fi, wine estate with Pool,Spa,restaurant,L6

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 58 minutes

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

1 of 2 filters match

Price per night from

$216

Flat with terrace,Wi-Fi, wine estate with Pool,Spa,restaurant,gym room,C6

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 58 minutes

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

1 of 2 filters match

Price per night from

$235

Flat with terrace,Wi-Fi, wine estate with Pool,Spa,restaurant,gym room,s6

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 58 minutes

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

1 of 2 filters match

Price per night from

$216

Flat with terrace,Wi-Fi, wine estate with Pool,Spa,restaurant,gym room,n4

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 58 minutes

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

1 of 2 filters match

Price per night from

$153

Flat with terrace,Wi-Fi, wine estate with Pool,Spa,restaurant,gym room,G4

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 58 minutes

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

1 of 2 filters match

Price per night from

$152

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), Pets allowed

1 of 2 filters match

Price per night from

$199

Vacation in Tuscany Montepulciano

Abbadia di Montepulciano house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

1 of 2 filters match

Price per night from

$186

Villa in Montepulciano ID 4124

Sant'Albino villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 19

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

1 of 2 filters match

Price per night from

$917

Viewing 38 of 113
rentals in Montepulciano

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