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  • Italy
  • Tuscany
  • Province of Siena
  • Montepulciano

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  • Abbadia di Montepulciano (3)
  • Acquaviva di Montepulciano (4)
  • Gracciano (3)
  • Sant'Albino (2)
  • Valiano (8)

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158 Holiday homes

Filters applied: Non-Smoking property (158)

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

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35827-Apartment Montepulciano - Abbadia di Montepulciano apartment sleeps 4

Montepulciano / Abbadia di Montepulciano

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 - £1050 / week

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from £102 / night

(7) Excellent 

1 / 41

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

Province of Siena / Montepulciano

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
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

1 / 100

Vino Nobile - Vigna - Montepulciano apartment sleeps 3

Province of Siena / Montepulciano

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
This charming cottage in Montepulciano affords a dining area and a living room with fireplace and single sofa bed, a kitchenette and a double/twin bedroom. The cottage also has its own private bathroom with shower.Outside, it features its own private terrace. The cottag  …see more

from £100 / night

£584 - £825 / week

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from £100 / night

1 / 17

Holiday Resort in Montepulciano M - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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. Next village, Acquaviva is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists of 2  …see more

from £46 / night

£321 - £671 / week

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from £46 / night

(41) Excellent 

1 / 21

La Casina Toscana, central with parking and wi-fi

Province of Siena / Montepulciano

3 bedroomsSleeps 53 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 158 km; Great for children of all ages ; 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 £59 / night

£334 - £584 / week

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from £59 / night

1 / 18

The Artist's Villa (v042) - Gracciano villa sleeps 9

Montepulciano / Gracciano

4 bedroomsSleeps 97 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
This unique villa has, on the ground floor, a large entrance hall, a large living room with kitchen, dining room and central fireplace, a double bedroom, a bedroom with french bed (which could sleep 2 people), a bathroom with a shower, a bathroom with bathtub. On the fi  …see more

from £202 / night

£1409 - £2300 / week

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from £202 / night

1 / 100

Cortona 15664 - Montepulciano villa sleeps 13

Province of Siena / Montepulciano

5 bedroomsSleeps 137 nights min stay

  • 5 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Charming share of an independent Tuscan villa rental affording extensive views over the surrounding landscape. The villa rental, offering tastefully furnished interiors, is quietly situated in a short distance from the lovely Tuscan town of Cortona (15 km). Distances: f  …see more

from £138 / night

£965 - £2146 / week

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from £138 / night

1 / 100

Valpoliziana - Montepulciano villa sleeps 8

Province of Siena / Montepulciano

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 50 km; Swimming pool; Great for children of all ages ;
Exteriorthe Villa boasts an absolutely perfect position, surrounded by rolling hills covered in vineyards and olive groves as far as the eye can see- the owners of the property in fact produce their own excellent wine and olive oil. Wonderful views from the villa also e  …see more

from £459 / night

£2084 - £3625 / week

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from £459 / night

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Villa Croce - Sant'Albino villa sleeps 10

Montepulciano / Sant'Albino

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 115 km; Swimming pool; Great for children of all ages ;
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 £227 / night

£1584 - £3000 / week

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from £227 / night

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Il Molinaccio di Montepulciano 1 - Montepulciano farmhouse sleeps 2

Province of Siena / Montepulciano

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; 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 £92 / night

£500 / week

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from £92 / night

1 / 100

Vino Nobile - Fontana - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
This enchanting suite in Montepulciano affords a dining-com-living area and a kitchen corner. The bedroom has a comfortable double bed and it affords an en-suite bathroom with whirlpool shower. The design of this suite is very peculiar, since the furniture has been crea  …see more

from £84 / night

£584 - £750 / week

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from £84 / night

(5) Excellent 

1 / 52

Province of Siena / Montepulciano

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Great for children of all ages ; Car not necessary; Some pets are welcome - please contact the owner;
 …see more

from £117 / night

£667 - £750 / week

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from £117 / night

1 / 100

Foiano Della Chiana 15663 - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Beautiful 5-hectare estate in Tuscany, a villa for wedding celebration and holidays, comprising a farmhouse of 140 m2 and an outbuilding of 60 m2 which have been skilfully restored and turned into a delightful independent villa offering tastefully and refined furnished  …see more

from £154 / night

£1072 - £2111 / week

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from £154 / night

1 / 100

Vino Nobile - Giardino - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
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 £100 / night

£625 - £875 / week

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from £100 / night

1 / 24

La Poliziana - 6 pax + kitchen - Montepulciano apartment sleeps 8

Province of Siena / Montepulciano

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
This apartment in Montepulciano hosting a maximum of 8 guests is approximately 95 sq-m and affords views of the surrounding beauty.The apartment  features a kitchen corner to try your hand at Tuscan cuisine and a lovely 3 double bedroom and 1 twin bedroom bedecked  …see more

from £274 / night

£1917 - £2500 / week

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from £274 / night

(3) Very Good 

1 / 24

Great place for a Tuscan family holiday, 2 bedroom countryside apartments with shared pool

Province of Siena / Montepulciano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
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 £67 / night

£0 / week

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from £67 / night

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Province of Siena / Montepulciano

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 116 km; Great for children of all ages ; Car advised;
 …see more

from £117 / night

£625 / week

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from £117 / night

1 / 11

Province of Siena / Montepulciano

1 bedroomSleeps 22 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Not suitable for children; Car advised; No pets allowed;
 …see more

from £59 / night

£367 / week

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from £59 / night

(5) Excellent 

1 / 24

Province of Siena / Montepulciano

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Great for children of all ages ; Car advised; No pets allowed;
 …see more

from £65 / night

£384 / week

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from £65 / night

(2) Excellent 

1 / 16

MONTEPULCIANO OLD TOWN - Montepulciano apartment sleeps 3

Province of Siena / Montepulciano

2 bedroomsSleeps 33 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min stay
Key info: Suitable for children age 5+; No pets allowed;
nice and comfortable apartment in the old town of Montepulciano Placed in the Historical Centre, just a few steps to the most beautiful and oldest wine cellar in Montepulciano (Cantina del Redi dè Ricci) an amazing sixteenth-century structure, great-looking with its  …see more

from £64 / night

£379 / week

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from £64 / night

1 / 33

Country House Maramai in the lush Chiana valley

Montepulciano / Gracciano

5 bedroomsSleeps 97 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £283 / night

£1975 - £3934 / week

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from £283 / night

1 / 100

Nobile - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 200 km; Swimming pool; Great for children of all ages ;
ExteriorVilla Nobile, a lovely farmhouse within a wine and olive oil producing estate boasts a perfect location, on a hill with panoramic views of the area, conveniently situated a few minutes drive from Montepulciano and well located to explore the wider area. Guests a  …see more

from £227 / night

£1584 - £2417 / week

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from £227 / night

(11) Excellent 

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CasaMontepulciano Into the sunset - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Great for children of all ages ; Some pets are welcome - please contact the owner;
.The apartment, Into The Sunset, owes its name to the magnificent views of the hills of Val d'Orcia which you can enjoy from its windows. It is located in the center of Montepulciano, via Collazzi 10, only 200 meters from Piazza Grande, the heart of the city, where you  …see more

from £96 / night

£584 - £724 / week

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from £96 / night

(18) Excellent 

1 / 24

The Beautiful Sun Apartment - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 bedroomsSleeps 61 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Nearest beach 170 km; Great for children of all ages ; Car not necessary;
This spacious and modern apartment (140sq.mt.) offers a pleasant, shining, fresh and convenient permanence in the core of Tuscany. It has two large bed rooms (25 sq.mt.), two large living rooms whose one with a new and fully equipped kitchen (dish washer machine include  …see more

from £100 / night

£583 - £1016 / week

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from £100 / night

(3) Excellent 

1 / 35

The Notary's House - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
Small charming flat, old residence of householder's great-grandfather, Notary in Montepulciano. Recently wholly restructured, very quiet, in a very beautiful position: in the centre of town, but facing the walls of the city, in a dominant position.Two nice bedrooms, sma  …see more

from £59 / night

£334 - £500 / week

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from £59 / night

(7) Excellent 

1 / 26

Province of Siena / Montepulciano

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Great for children of all ages ; Car essential; Air conditioning;
 …see more

from £67 / night

£409 - £525 / week

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from £67 / night

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AIA - 60 sq mt - La casa delle Querce - Acquaviva di Montepulciano farmhouse sleeps 5

Montepulciano / Acquaviva di Montepulciano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
L'AIA it's a homy apartment of 60 sq mt. Climbing few doorsteps you enter the living-dining room embellished by brick walls,wooden beamed ceilings and local terracotta tiled floors. In the living-dining room there is a dining table, a sofa, some rustic Tuscan furniture,  …see more

from £84 / night

£500 - £892 / week

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from £84 / night

(1) Excellent 

1 / 18

Province of Siena / Montepulciano

2 bedroomsSleeps 71 night min stay

  • 2 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Great for children of all ages ; Pets welcome; Private garden;
 …see more

from £55 / night

£350 - £496 / week

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from £55 / night

1 / 100

Petit Verdot - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
ExteriorsOriginally built in the 17th century rural Tuscany, the Villa has been restored without altering its original architecture. Siena's typical ocher colors dominate the villa's stone walls and diffuse a welcoming glow on the light blue of the infinity po  …see more

from £417 / night

£2917 - £3250 / week

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from £417 / night

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il Molinaccio Montepulciano 3 - Montepulciano farmhouse sleeps 6

Province of Siena / Montepulciano

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; 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 £250 / night

£1459 / week

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from £250 / night

1 / 100

Albino - Montepulciano villa sleeps 14

Province of Siena / Montepulciano

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Nearest beach 180 km; Swimming pool; Great for children of all ages ;
ExteriorVilla Albino is a sophisticated and at the same time relaxed villa for 14 people in Tuscany. It is conveniently located just 5km away from Montepulciano, a privileged position to explore all of central Italy. It is within easy reach of Pienza, Montalcino, Bagno,  …see more

from £334 / night

£2334 - £5167 / week

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from £334 / night

(1) Excellent 

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Holiday Resort in Montepuciano B - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 bedroomSleeps 44 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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. Next village, Acquaviva is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists of 2  …see more

from £57 / night

£400 - £788 / week

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from £57 / night

(11) Excellent 

1 / 33

Pretty 2 bedroom holiday apartment in the heart of

Province of Siena / Montepulciano

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Great for children of all ages ; Car not necessary; Some pets are welcome - please contact the owner;
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 £75 / night

£434 - £552 / week

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from £75 / night

1 / 10

Agriturismo Terrarossa 2 pax - Valiano apartment sleeps 2

Montepulciano / Valiano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
The apartment "Rosa" (2 persons), with furniture of epoch, is composed of a stay- kitchen with read couch, a double bedroom and a bathroom with shower. In bedroom: tv sat. The Terrarossa agriturism complex is situated on one of the most beautiful and panoramic  …see more

from £80 / night

£375 - £505 / week

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from £80 / night

1 / 27

Agriturismo Ardene - Montepulciano villa sleeps 14

Province of Siena / Montepulciano

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 100 km; Swimming pool;
Villa Ardene provides its guests with high level services in a magical, peaceful and unforgettable atmosphere. All the suites and apartments are equipped with whirlpool bath, air conditioning, satellite TV, internet connection.The interior space in “arte povera” has  …see more

from £565 / night

£3956 - £6060 / week

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from £565 / night

1 / 13

Casa al bosco - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; 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 £92 / night

£642 - £817 / week

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from £92 / night

(9) Excellent 

1 / 25

The Little Arch of Memory - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Great for children of all ages ; No pets allowed;
The Little Arch of Memory is a cute first floor apartment placed in the core of Montepulciano and at few steps from the main square, the old theater and the old main street, but yet in a parallel and quiet street. This 45 sq.mt. apartment is full of old history and my f  …see more

from £75 / night

£391 - £441 / week

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from £75 / night

1 / 100

Vino Nobile - Girasole - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
This is a large stone cottage with wonderful views over the Tuscan countryside and the swimming pool of the property. It affords a dining area and a living room with fireplace and double sofa bed, a kitchen area and two double bedrooms with their en-suite bathrooms (one  …see more

from £167 / night

£1167 - £1659 / week

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from £167 / night

(1) Excellent 

1 / 36

POLICIANO Suite, 90 sq mt - La Casa delle Querce

Montepulciano / Acquaviva di Montepulciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
The POLICIANO Suite is the largest apartment of La Casa delle Querce with its 90 sq meters. It comprises of a very spacious living dining-room, an ample cooking area, two bedrooms and two bathrooms each with shower. In the bedrooms there is air conditioning. One bedroom  …see more

from £117 / night

£700 - £1125 / week

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from £117 / night

(5) Excellent 

1 / 20

Montorio - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed;
Montorio was built in 1300 as a convent and is located in the beautiful sopt in MOntepulciano , on the top of a private hill overlooking the church of San Biagio and the rolling hill. It is in a walking distance to the center of the town but ensure the privacy of a coun  …see more

from £109 / night

£750 / week

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from £109 / night

Top Destination reviews

The Beautiful Sun Apartment
Well maintained apartment and very helpful owner

Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and everything we needed was there. All to a good s … 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 thoughtf … see more
The Grifo Apartment
Perfect!!

The apartment is spacious and clean. It's inside the historical center and it's perfect to visit it. We had a quiet stay . … see more

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