50 Best Montepulciano Apartment rentals on Holiday Lettings - Villas

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Montepulciano

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270 Vacation rentals

(9) Very Good 

6

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Pet friendly

from $55 / night

$380 / week

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from $55 / night

(11) Excellent 

21

Gracciano Vacation cottage rental

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
The cottage is opposite the owner's house and consists of two double bedrooms, two bathrooms and a large living room with cooking area. The living area opens onto a patio and pergola and the downstairs bedroom also opens onto a small patio. There is access for the disa …see more

from $87 / night

$478 - $2235 / week

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from $87 / night

(1) Very Good 

18

B&b rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
In the beautiful ancient Villa ( 1812 ) of the of " Tenuta Argiano in Montepulciano " estate , we rent some bedrooms in B&B treatment . our guest are treated like part of the family and if request they can join the dinner with the owners. this place is ideal also for …see more

from $38 / night

$266 / week

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from $38 / night

24

Montepulciano / Abbadia di Montepulciano

8 7 1 night min

  • 8 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 70 mi
  • Child friendly
  • Air conditioning

from $217 / night

$1302 / week

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from $217 / night

(9) Very Good 

41

Vacation farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 mi
  • 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 for …see more

from $128 / night

$800 - $1146 / week

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from $128 / night

4

Montepulciano / Gracciano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 200 mi
  • Child friendly
  • Ask about pets

Pricing unknown

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Pricing unknown

(6) Very Good 

45

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

from $93 / night

$602 - $656 / week

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from $93 / night

11

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

from $76 / night

$478 / week

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from $76 / night

(2) Excellent 

16

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Suitable for children age 5+
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 h …see more

from $82 / night

$489 / week

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from $82 / night

(1) Excellent 

23

Vacation villa with shared pool in Montepulciano

Province of Siena / Montepulciano

4 2 Min stay varies

  • 4 bedrooms
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Ask about children
in Villa Argiano in Montepulciano, we have several possibilities : B&B in Argiano's villa rooms ( three ) or self catering apartments ( two + one extra room ). In this beautiful Villa, were we live , at the second floor of the house we rent three bedrooms in b&b …see more

from $38 / night

$266 / week

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from $38 / night

(1) Excellent 

29

Province of Siena / Montepulciano

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from $315 / night

$1736 - $2495 / week

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from $315 / night

(14) Excellent 

25

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
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 $98 / night

$513 - $579 / week

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from $98 / night

17

Vacation apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $71 / night

$445 - $874 / week

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from $71 / night

21

Valiano Vacation farmhouse rental

Montepulciano / Valiano

5 13 7 nights min

  • 5 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
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: …see more

from $179 / night

$1248 - $2767 / week

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from $179 / night

(49) Excellent 

21

Vacation cottage in Montepulciano

Province of Siena / Montepulciano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 158 mi
  • Child friendly
  • Air conditioning
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 $93 / night

$543 - $760 / week

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from $93 / night

(3) Very Good 

24

Vacation farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 200 mi
  • Swimming pool
  • Child friendly
Villa Pietra del Diavolo, recently restored, is situated in one of the most beautiful and panoramic hill around Montepulciano. “Pietra del Diavolo” is named after a stone composed of tufa layers particularly common in the local area. The property is situated in th …see more

from $295 / night

$2062 - $3689 / week

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from $295 / night

(12) Excellent 

24

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
.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 $125 / night

$760 - $942 / week

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from $125 / night

(6) Excellent 

16

Farmhouse rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Podere san Pietro is an ancient country house held in brick and stones with a living surface of 350 sqm. for a total of 3bathroom and 4 bedrooms, which accommodate up to 10 people , in addition to private swimming pool of 11X5 mt The house has been recently restored …see more

from $217 / night

$1519 / week

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from $217 / night

20

Montepulciano Vacation farmhouse rental

Province of Siena / Montepulciano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful independent villa in Tuscany has a private swimming pool and rests just 2km from the historical centre of charming Montepulciano. The property is well looked after and ideally positioned for visiting the beautiful Val d’Orcia area (Pienza, San Quirico d’O …see more

from $185 / night

$1085 - $2224 / week

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from $185 / night

(8) Excellent 

33

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 mi
  • 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 $76 / night

$532 / week

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from $76 / night

55

Montepulciano / Valiano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from $158 / night

$923 / week

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from $158 / night

(4) Very Good 

24

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 mi
  • 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 $76 / night

$532 / week

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from $76 / night

(1) Excellent 

7

Farmhouse rental in Montepulciano with shared pool

Province of Siena / Montepulciano

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Located in a panoramic position on a hill crest between the Val d'Orcia and Valdichiana near Montepulciano, Agriturismo Il Casalone offers a holiday unit tastefully furnished in Tuscan country style. One double bed room (king size), one bathroom and a living room with k …see more

from $76 / night

$326 - $565 / week

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from $76 / night

(2) Very Good 

20

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $87 / night

$548 - $1026 / week

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from $87 / night

40

Vacation farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
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 spen …see more

from $119 / night

$646 / week

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from $119 / night

99

Montepulciano / Abbadia di Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden

from $543 / night

$3797 / week

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from $543 / night

(1) Excellent 

22

Province of Siena / Montepulciano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 116 mi
  • Child friendly
  • Pet friendly

from $152 / night

$651 - $814 / week

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from $152 / night

(9) Excellent 

52

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

from $152 / night

$923 / week

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from $152 / night

(7) Very Good 

19

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly

from $120 / night

$651 / week

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from $120 / night

21

Vacation b&b in Acquaviva di Montepulciano

Montepulciano / Acquaviva di Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Tenuta di Argiano a Montepulciano, located near MONTEPULCIANO, is surrounded by vineyards growing grapes for the famous local wines, Vino Nobile di Montepulciano and Rosso di Montepulciano, and is peaceful and quite. swimming pool and wifi . bikes tour, spa nearby, It …see more

from $74 / night

$517 / week

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from $74 / night

24

Montepulciano Vacation apartment rental

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
Apartment Il Casale is located in Tuscany in Montepulciano. This is a typical countryside house immersed in the greenery. The building is divided in two parts; in one of them the owners live, while the other is for guests. The apartment can accommodate 4 people; it cons …see more

from $163 / night

$706 - $923 / week

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from $163 / night

20

Province of Siena / Montepulciano

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Ask about pets

from $76 / night

$651 - $1107 / week

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from $76 / night

(2) Excellent 

17

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearestt village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists …see more

from $120 / night

$684 - $1253 / week

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from $120 / night

6

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly

from $76 / night

$478 - $836 / week

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from $76 / night

(7) Very Good 

22

Province of Siena / Montepulciano

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly

from $98 / night

$575 / week

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from $98 / night

31

Montepulciano Vacation villa rental

Province of Siena / Montepulciano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Private garden
Il Poggiarone is a splendid farmhouse with typical Tuscan architectural features, set in an extremely panoramic position and the ideal destination for those who are looking for a holiday which is a mix of art, history and nature. The beautiful villa is near the owner's …see more

from $205 / night

$1432 - $2647 / week

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from $205 / night

10

Valiano Vacation apartment rental

Montepulciano / Valiano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • 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 h …see more

from $109 / night

$521 - $651 / week

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from $109 / night

24

Vacation villa in Montepulciano

Province of Siena / Montepulciano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Poliziano is located on a hill, immersed in the countryside, among woods and olive groves. It is only 500 meters from the village of S.Albino in the south of Tuscany and 5 minutes drive from Montepulciano. The location is excellent for touring in central Italy; yo …see more

from $496 / night

$3472 - $6726 / week

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from $496 / night

14

Province of Siena / Montepulciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from $82 / night

$543 - $640 / week

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from $82 / night

(18) Excellent 

24

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 170 mi
  • Child friendly
  • 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 $130 / night

$759 - $1290 / week

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from $130 / night

1