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Holiday Lettings
> Europe
> Italy
> Tuscany
> Province of Siena
> Villas and apartments in Montepulciano

Villas in Montepulciano and Apartments - Holiday Lettings - Holiday Rentals Montepulciano

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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405 Holiday homes

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Holiday villa with swimming pool in Valiano

Valiano villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10
1 review

from £121 / night

£844 / week

1 / 18

Apartment rental in Montepulciano with shared pool

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
1 review

from £145 / night

£1,013 / week

1 / 18

Holiday b&b in Acquaviva di Montepulciano

Acquaviva di Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £87 / night

£608 / week

1 / 29

Holiday condo in Montepulciano

Montepulciano condo

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11
1 review

from £174 / night

£1,447 / week

1 / 35

Holiday apartment in Acquaviva di Montepulciano

Acquaviva di Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £116 / night

£772 - £1,447 / week

1 / 20

Holiday villa with swimming pool in Montepulciano

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14
1 review

from £1,061 / night

£6,944 / week

1 / 51

Acquaviva di Montepulciano holiday apartment let

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £77 / night

£675 - £946 / week

1 / 11

Lodge rental in Abbadia di Montepulciano

Abbadia di Montepulciano lodge

  • 8 bedrooms
  • 3 bathrooms
  • sleeps 7

from £193 / night

£1,158 / week

1 / 24

Holiday b&b with swimming pool in Montepulciano

Montepulciano b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

from £965 / night

£6,751 / week

1 / 44

Holiday apartment in Bivio di San Biagio

Bivio di San Biagio apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £319 / night

£2,228 / week

1 / 6

Montepulciano holiday villa rental

Montepulciano villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £126 / night

£772 / week

1 / 18

Holiday farmhouse in Montepulciano

Montepulciano farmhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

from £242 / night

£1,254 / week

1 / 12

B&b rental in Montepulciano

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £116 / night

£811 / week

1 / 5

Holiday b&b in Montepulciano

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £97 / night

£675 / week

1 / 5

Holiday villa rental

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

from £590 / night

£4,128 / week

1 / 45

Montepulciano holiday b&b rental

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £82 / night

£483 / week

1 / 11

Holiday apartment in Montepulciano

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
7 reviews

from £135 / night

£772 / week

1 / 12

Holiday farmhouse in Montepulciano

Montepulciano farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £78 / night

£540 / week

1 / 8

Holiday apartment in Montepulciano

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £111 / night

£777 / week

1 / 5

Holiday apartment accommodation

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £135 / night

£820 / week

1 / 8

Holiday villa rental

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

from £675 / night

£4,625 - £7,663 / week

1 / 48

Holiday b&b with shared pool in Montepulciano

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £184 / night

£1,216 / week

1 / 11

Montepulciano holiday b&b rental

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £242 / night

£1,553 / week

1 / 4

Holiday villa with swimming pool in Montepulciano

Montepulciano villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

from £174 / night

£1,216 / week

1 / 37

Holiday home with swimming pool in Bivio di San Biagio

Bivio di San Biagio house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £760 / night

£4,640 - £7,690 / week

1 / 23

Villa rental in Montepulciano with swimming pool

Montepulciano villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 16
3 reviews

from £573 / night

£3,610 / week

1 / 38

Montepulciano holiday b&b rental

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £82 / night

£483 / week

1 / 12

Holiday apartment in Cervognano

Cervognano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £159 / night

£1,108 - £1,249 / week

1 / 28

Abbadia di Montepulciano holiday home rental

Abbadia di Montepulciano house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £145 / night

£772 / week

1 / 6

Sant'Albino holiday villa rental

Sant'Albino villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 19

from £717 / night

£5,016 / week

1 / 42

Montepulciano holiday b&b accommodation

Montepulciano b&b

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4
1 review

from £97 / night

£675 / week

1 / 14

Montepulciano holiday apartment rental

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £145 / night

£1,013 / week

1 / 17

Montepulciano holiday apartment let

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
8 reviews

from £68 / night

£463 - £1,138 / week

1 / 11

Holiday apartment in Montepulciano

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £87 / night

£483 / week

1 / 28

Montepulciano holiday apartment rental

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £79 / night

£554 / week

1 / 21

Holiday apartment in Montepulciano

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £103 / night

£716 / week

1 / 28

Holiday apartment in Cervognano

Cervognano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £159 / night

£1,000 - £1,249 / week

1 / 27

Holiday guest house rental

Montepulciano guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £155 / night

£965 / week

1 / 22

Apartment rental in Montepulciano

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
2 reviews

from £113 / night

£671 - £860 / week

1 / 25

Holiday villa in Bivio di San Biagio

Bivio di San Biagio villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £567 / night

£3,970 / week

1 / 52

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Montepulciano holidays

Montepulciano is a beautiful village in a hilly area of Tuscany overlooking the Valdichiana countryside. The streets here leave a lasting impression on visitors because of their old world charm and also because of their steep inclines, which can make an adventure out of an ordinary day spent exploring markets and relaxing in cafes.

These sloping streets wind amongst some unforgettable restaurants and wine cellars. They can also take you to some of the most beautiful renaissance churches in Tuscany. Head beyond the centre of town and take a hike through the rolling countryside of world famous vineyards and olive groves. At the end of the day, head back to experience the delicious cuisine that brings knowledgeable foodies to Montepulciano from all over the world and enjoy a glass of vino nobile as the sun sets.

Here are a few additional suggestions as you plan your trip:

  • Visit the Chiesa di San Biagio: This domed renaissance church with its fantastic marble alter piece lies in a valley just to the west of the Chiesa del Gesu, another impressive work of religious architecture.
  • Explore the Museo Civico: The town of Montepulciano has its own civic museum, which houses artefacts documenting its long history.
  • Explore the cantinas of Montepulciano: Tuscany is known for its wine, but Montepulciano in particular has a charming community of cantinas that offer tours through cellars packed with casks followed by a unique tasting experience.
  • Take a tour of the Azienda Agricola Canneto: This sprawling vineyard close to the Church of San Biagio produces regional vino nobile and extra virgin olive oil. Come to tour the grounds and learn more about how these precious items are produced.
  • Take an Italian cooking class: Sample the unforgettable flavours of Tuscany at the restaurants and trattorias of Montepulciano, then take a course from a skilled chef and learn how to bring these flavours home with you.
  • Visit the Formaggi Cugusi Silvana: The family that runs this artisanal pecorino cheese shop makes cheese with the milk from their own sheep that graze in the pastures of theVal d'Orcia.

You'll have no trouble finding world class dining opportunities, and you'll also have no trouble finding a holiday rental that offers luxurious views of the Tuscan countryside. Find an elegant condo downtown or a beautiful rustic villa overlooking the vineyards. While you're visiting Montepulciano, you may want to include a day trip to the beautiful town of Torrita di Siena in your plans.

Top Destination reviews

Charming Cottage in Peaceful Country Setting - Sleeps 6
We will come back!

It was great staying here! We found a nice little place to feel at home. The cottage is lovely furnished, very clean and has everything we needed for the week (including fast heating for some rainy and cold evenings (20minutes was enough to get the humid air out!) and free Wi-Fi, thats working perfectly and fast). We really loved sitting in the beautiful garden full of roses, looking over the wine-yards and listening to all the birds (also nightingales!!!). The cottage is set in a great surrounding - Tuscany like in a picture book! Laura was a perfect host. We felt very welcomed, we could ask her for everything and she could give us good hints for restaurants, hiking-paths and everything else you need to know for holiday. Thank you very much, Laura! … see more
7 bedroom Tuscan farmhouse near rennaissance town of Montepulciano, features include jacuzzi, private garden and pool
Wonderful place, we'll come back!

Everything was first class: the rooms, the pool, breakfast, the countryside. We enjoyed a walk in the countryside and had an archery session with a very patient instructor. Staff is very friendly and helpful. … see more
Tenuta di Argiano in Montepulciano, apartment, winery, pool, wifi
Excellent with children or groups

We had very enjoyable stay in a peaceful location with stunning views around. Olimpia was very helpful and everything worked as foreseen. We were trying to find a place with a scent of a history and what would suit better than 200 years old house with modern amenities! A very big garden where you have slide and toys for the youngest ones and soccer goals for elders is so good for us parents! We could just sit and relax in the garden while children were playing. It was still too cold for swimming but I can just imagine the joy of children (and us, of course) in the summertime. There was a gate to the pool area so we did not even have to worry about our nearly 2 year old getting to the pool on her own. Chicken, donkey and horse were a nice extra for all this. The only minus was that Wi-fi did not work inside the apartment. We could still make the further trip reservations in a spot in courtyard where there was signal for Wi-fi. I wonder if the walls of the apartment were so thick that there was not signal for that reason. … see more
Holiday Apartment in the historical palace.Marina
Lovely Place to Stay!

This is a spacious and elegant apartment in an historic building. It was very clean and pleasantly decorated. The beds were comfortable with good linens; bathrooms were spacious and clean with good shower pressure. The kitchen more than adequate (we do cook, too many meals out can be boring and costly). As with several of our Italian rentals, there was no automatic coffee machine. Perhaps the only caveat was that the building’s elevator, which we were advised was “sensitive”, didn’t work for us. If climbing stairs are an issue this could be a problem, but we told ourselves the exercise was good after eating some great Italian dishes! We look forward to returning to this property. … see more
La Casina Toscana, central with parking and wi-fi
Clean, comfortable and cozy house with privacy and convenience to Montepuciano

We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close enough to walk to the Montepulciano town. The place was very clean and thoughtfully renovated. It also has a nice view of the town and the Tuscan landscape. We were there in Dec so were able to make use of the wood-burning fireplace that added to the coziness. The whole rental experience was very pleasant as Davide was extremely responsive and provided helpful information from arrival to departure. We highly recommend the place and would not hesitate to go back again! … see more

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