Montepulciano Villas, Apartments and holiday rentals

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  • Italy
  • Tuscany
  • Province of Siena
  • Montepulciano
  • All locations
  • Abbadia di Montepulciano (4)
  • Acquaviva di Montepulciano (4)
  • Gracciano (5)
  • Sant'Albino (5)
  • Valiano (12)

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185 Holiday homes

Travellers going to Montepulciano are booking September dates now. Secure your holiday home today and have the perfect trip.

1 / 18

Province of Siena / Montepulciano

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Child friendly ; Pet friendly;
 …see more

from £69 / night

£479 / week

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from £69 / night

(1) Excellent 

1 / 17

Casa Vacanze I Chiari - Montepulciano guest house sleeps 16

Province of Siena / Montepulciano

7 16 2 nights min stay

  • 7 bedrooms
  • Sleeps 16
  • 2 nights min stay
Key info: Not suitable for children; No pets allowed;
On the border between Tuscany and Umbria arises our ancient farmhouse, remodelled in order to make you feel more at home and to make it more comfortable, without giving up the characteristics of the Tuscan country house.The location is perfect for artistic and cultural  …see more

from £855 / night

£5983 / week

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from £855 / night

1 / 5

ARDENEX2 - Montepulciano farmhouse sleeps 2

Province of Siena / Montepulciano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car advised;
Ardene is located in Montepulciano and due to its unexpected, innovative and welcoming accommodation facilities it is one of the most exclusive farmhouse of this area. It is a country house in ancient stone and its origins date back to the medieval times. Ardene is the  …see more

from £103 / night

£718 / week

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from £103 / night

1 / 26

Villa Croce - Sant'Albino villa sleeps 10

Montepulciano / Sant'Albino

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 115 km; Swimming pool; Child friendly ;
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano. The property is situated in the heart a working farm with breathtaking views over the valley where Vino Nobile di Montepulciano is produced. The villa ha  …see more

from £232 / night

£1624 - £3077 / week

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from £232 / night

1 / 29

Province of Siena / Montepulciano

5 9 1 night min stay

  • 5 bedrooms
  • Sleeps 9
  • 1 night min stay
Key info: Swimming pool; Not suitable for children; Car advised;
 …see more

from £855 / night

£5983 / week

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from £855 / night

(41) Excellent 

1 / 21

La Casina Toscana, central with parking and wi-fi - Montepulciano cottage sleeps 5

Province of Siena / Montepulciano

3 5 3 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 158 km; Child friendly ; Car advised;
Placed in the countryside of Montepulciano, near the most important historical towns such as Pienza, Montalcino and Bagno Vignoni, the Casina Toscana is a historical residence of the nineteenth century, which allows guests to enjoy the tranquility and relaxation that th  …see more

from £60 / night

£342 - £599 / week

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from £60 / night

1 / 100

Vino Nobile - Giardino - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Child friendly ;
Located amidst the enchanting garden of the property, this independent cottage in Montepulciano affords a dining area and a living room with fireplace and double sofa bed, a kitchen with its own breakfast area, and a double bedroom with its en-suite bathroom equipped wi  …see more

from £103 / night

£642 - £838 / week

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from £103 / night

1 / 20

Province of Siena / Montepulciano

2 6 3 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £86 / night

£513 - £633 / week

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from £86 / night

1 / 12

Province of Siena / Montepulciano

4 7 1 night min stay

  • 4 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £214 / night

£1112 / week

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from £214 / night

(6) Excellent 

1 / 33

Lovely 2 bedroom holiday apartment in Tuscany - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 120 km; Swimming pool; Child friendly ;
The apartment Tino is 55 Square meters and accommodates up to 4 people. First floor is composed of sitting/dining room with cooking area (dishwasher) and fireplace, 2 bedrooms, 1 bathroom with shower. sofabed for one people in living room for a child. In the garden ,  …see more

from £65 / night

£449 / week

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from £65 / night

1 / 11

Province of Siena / Montepulciano

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Car advised; Ask about pets;
 …see more

from £30 / night

£210 / week

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from £30 / night

(11) Excellent 

1 / 33

Pretty 2 bedroom holiday apartment in the heart of - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Car not necessary; Ask about pets;
CasaMontepulciano is a flat of roughly 60 sq m (646 sq ft), located in via Cagnano 9. Restored in 2011 it is has high quality finishes and exposed beams. It consists of a large living room/kitchen, two bedrooms (one of which is a master bedroom but in the other room i  …see more

from £65 / night

£342 - £566 / week

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from £65 / night

1 / 5

Province of Siena / Montepulciano

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £103 / night

£718 / week

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from £103 / night

1 / 16

Luxury 4 bed house with views over Montepulciano - Montepulciano farmhouse sleeps 8

Province of Siena / Montepulciano

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Child friendly ; Car essential; No pets allowed;
This luxury 4 bedroom villa is furnished throughout to a high standard. The property sits in 4 acres of garden, surrounded by woods and vineyards. All the bedrooms have en-suite marble bathrooms and fantastic views of either Montepulciano or Montefollonico. Outside the  …see more

from £306 / night

£2137 - £2308 / week

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from £306 / night

1 / 6

Rosa Apartment - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 4 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 4 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
The Terrarossa farm holiday resort is deep in the stunning hills around Montepulciano.It is part of an ancient country estate counting 130 acrwes land, where with respect for the land and its natural balance wheat, sunflowers and, above all, the vines for Vino Nobile di  …see more

from £129 / night

£642 / week

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from £129 / night

1 / 15

35827-Apartment Montepulciano - Abbadia di Montepulciano apartment sleeps 4

Montepulciano / Abbadia di Montepulciano

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car not necessary;
Elegant house restored in the second half of the 1800s. It is situated in a property of approximately 12 hectares where there are olive trees and a vineyard from which an excellent Chianti wine (D.O.C.G.) and the famous Nobile di Montepulciano (D.O.C.G.) wine are made.  …see more

from £102 / night

£710 - £803 / week

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from £102 / night

1 / 9

Province of Siena / Montepulciano

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £52 / night

£300 - £599 / week

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from £52 / night

1 / 6

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; No pets allowed;
 …see more

from £52 / night

£257 / week

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from £52 / night

(5) Very Good 

1 / 23

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Child friendly ; Ask about pets; Private garden;
 …see more

from £73 / night

£471 - £565 / week

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from £73 / night

(1) Excellent 

1 / 18

Province of Siena / Montepulciano

2 7 1 night min stay

  • 2 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £56 / night

£359 - £509 / week

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from £56 / night

1 / 9

Province of Siena / Montepulciano

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Not suitable for children; No pets allowed;
 …see more

from £56 / night

£359 / week

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from £56 / night

1 / 6

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; No pets allowed;
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from £60 / night

£377 - £659 / week

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from £60 / night

1 / 23

I Tigli - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 115 km; Swimming pool; Child friendly ;
I Tigli is a splendid apartment with two bedrooms and two bathrooms which is part of a property with a total of 6 apartments sharing a pool. Located in the magnificent atmosphere of the hills surrounding the ancient town of Montepulciano, famous for its history, art, ar  …see more

from £99 / night

£642 - £847 / week

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from £99 / night

1 / 83

il Molinaccio Montepulciano 3 - Montepulciano farmhouse sleeps 6

Province of Siena / Montepulciano

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car essential;
The watermill “Il Molinaccio”, near the renaissance town of Montepulciano, was already present in the old maps of the Granduchy of Tuscany . The original building, duly and let me say passionately restored, now reopens as a luxury country house where the guests may  …see more

from £257 / night

£1496 / week

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from £257 / night

1 / 28

Villa San Biagio - Montepulciano villa sleeps 16

Province of Siena / Montepulciano

7 16 7 nights min stay

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Nearest beach 115 km; Swimming pool; Child friendly ;
Villa San Biagio is situated close to the hilltop town of Montepulciano renowned for its historical importance and for its wine Nobile. This magnificent country house is one of the most exclusive and stunning farmhouses in the area. The restoration works carefully prese  …see more

from £535 / night

£3740 - £5877 / week

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from £535 / night

1 / 17

Holiday Resort in Montepulciano M - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearest village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists  …see more

from £48 / night

£330 - £689 / week

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from £48 / night

1 / 6

Province of Siena / Montepulciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Swimming pool; Child friendly ; No pets allowed;
 …see more

from £60 / night

£359 - £556 / week

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from £60 / night

1 / 13

Casa al bosco - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
“Casa al bosco” is an elegant house restored in the second half of the 1800s. It is situated in a property of approximately 12 hectares where there are olive trees and a vineyard from which an excellent Chianti wine (D.O.C.G.) and the famous Nobile di Montepulciano  …see more

from £95 / night

£659 - £770 / week

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from £95 / night

1 / 14

Province of Siena / Montepulciano

4 9 3 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £770 / night

£3932 / week

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from £770 / night

(5) Very Good 

1 / 52

Province of Siena / Montepulciano

2 5 2 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Child friendly ; Car not necessary; Ask about pets;
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from £137 / night

£727 - £770 / week

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from £137 / night

(1) Excellent 

1 / 20

Holiday Resort in Montepuciano B - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 4 4 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearest village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists  …see more

from £59 / night

£411 - £808 / week

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from £59 / night

(2) Excellent 

1 / 25

Province of Siena / Montepulciano

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
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from £120 / night

£770 / week

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from £120 / night

1 / 33

Country House Maramai in the lush Chiana valley - Gracciano villa sleeps 9

Montepulciano / Gracciano

5 9 7 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Maramai lies on the Gracciano estate, one of the most renowned producers of the Vino Nobile di Montepulciano, one hour south of Florence in the lush Chiana valley. The restored farmhouse with pool with 7 to 9 beds is the perfect base to explore the surrounding Tuscany l  …see more

from £290 / night

£2026 - £3411 / week

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from £290 / night

1 / 11

Val di Chiana Farmhouse 627002 - Montepulciano farmhouse sleeps 18

Province of Siena / Montepulciano

9 18 4 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 4 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
Between the hills of Val di Chiana and the Val d'Orcia lying, while not far away from Umbria and Lake Trasimeno. It is a good starting point for trips to Montepulciano, Cortona, Montalcino, Chianciano (spa), Siena, Arezzo and Perugia. Montepulciano is not only famo  …see more

from £684 / night

£3505 / week

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from £684 / night

1 / 11

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Child friendly ; No pets allowed;
 …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

1 / 19

Province of Siena / Montepulciano

6 12 1 night min stay

  • 6 bedrooms
  • Sleeps 12
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
 …see more

from £119659 / night

£837607 / week

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from £119659 / night

(7) Excellent 

1 / 41

Unique, charming farmhouse in Tuscany countryside with shared outdoor pool, sleeps up to 6 - Montepulciano farmhouse sleeps 6

Province of Siena / Montepulciano

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Child friendly ;
The main arched entrance leads past a utility room and downstairs bathroom into the open plan kitchen and dining room with dining table for 6 guests. The lounge has two sofa's one of which is a comfortable double sofa bed There is a wood burning stove in the lounge  …see more

from £72 / night

£500 - £890 / week

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from £72 / night

(8) Very Good 

1 / 11

Belguardo - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Child friendly ; Car advised; Ask about pets;
The large apartment (116 sqm) is situated in the historical centre of Montepulciano. It is situated on the first floor of a historical building whose entrance opens onto the main street, a few steps from the most important archway (Porta al Prato) leading to the art tow  …see more

from £60 / night

£402 - £1072 / week

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from £60 / night

(3) Very Good 

1 / 24

Great place for a Tuscan family holiday, 2 bedroom countryside apartments with shared pool - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Child friendly ;
Tenuta di Argiano a Montepulciano Please ask always AVAILABILITY , we will find in one of our structures the ideal place for your holiday. CAR IS NECESSARY WE ARE IN THE MIDDLE OF COUNTRYSIDE, SURROUNDED BY NATURE. The beautiful apartment FIASCO (60square Mt) , FOR  …see more

from £69 / night

£479 / week

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from £69 / night

(1) Excellent 

1 / 63

Villa Bossona - Montepulciano villa sleeps 16

Province of Siena / Montepulciano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
Key info: Nearest beach 115 km; Swimming pool; Child friendly ;
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town. A small church with an enchanting bell tower is preserved in its original for  …see more

from £513 / night

£3334 - £3676 / week

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from £513 / night

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