50 Best Montepulciano Apartment rentals on Holiday Lettings - Villas

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Montepulciano

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4,403 Vacation rentals

(11) Excellent 

33

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
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 $113 / night

$649 - $789 / week

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Responds fast!
avg. 3 hours 32 minutes

from $113 / night

12

Vacation farmhouse in Montepulciano

Province of Siena / Montepulciano

4 7 1 night min

  • 4 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
Sunflower B&B is situated on a hill, along the road to Pienza a few hundred meters from the Temple of San Biagio and the cross-roads for Chianciano Terme. Enjoys a panoramic position, only in the area, allowing more than the sight of Montepulciano and Montefollonico tha …see more

from $312 / night

$1,623 / week

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from $312 / night

(2) Excellent 

26

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The palazzo dei Diavoli is a small holiday structure composed of 1) an apartment-independent SORBIAN House, with 2 bedrooms, 2 bathrooms, a fully equipped kitchen, terrace and independent equipped garden, air conditioning inside, suitable for small families or 2 couples …see more

from $149 / night

$869 / week

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from $149 / night

(1) Excellent 

18

Vacation apartment rental

Province of Siena / Montepulciano

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
90 sqm apartment with wide living room and fireplace. The House is rustic with wooden table and straw chairs (see photo) has two large rooms and a smaller apartment is located on the ground floor, directly on the garden, so easily accessible, overlooking the countryside …see more

from $82 / night

$537 - $986 / week

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Responds fast!
avg. 1 hour 48 minutes

from $82 / night

(1) Excellent 

18

Montepulciano Vacation home rental

Province of Siena / Montepulciano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
An independent holiday home has a private garden surrounded by silence and stillness of the splendid Tuscan countryside, less than 2 km from the center of Montepulciano. The house is part of a complex that consists of three structures, each with a different reception ca …see more

from $131 / night

$918 / week

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from $131 / night

24

Lodge rental in Abbadia di Montepulciano

Montepulciano / Abbadia di Montepulciano

8 7 1 night min

  • 8 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 70 mi
  • Child friendly
  • Air conditioning
It is a unifamiliaire House on two floors in a small village in Tuscany - Abbadia di montepulciano – near Siena and Montepulciano. Leasing is particular because the House is located between many small extraordinary cities, ad example: Montalcino, Pienza, the Amorosa, Ba …see more

from $250 / night

$1,498 / week

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from $250 / night

(1) Excellent 

11

Montepulciano Vacation home rental

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
The House of Calle welcomes you in the heart of Montepulciano. An old apartment in the historic center, between Piazza Grande and the main course, thoroughly and recently renovated. The house is situated on the ground floor and consists of two comfortable bedrooms (doub …see more

from $156 / night

$820 - $931 / week

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from $156 / night

83

Vacation farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 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 $375 / night

$2,184 / week

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Responds fast!
avg. 3 hours 10 minutes

from $375 / night

(10) Excellent 

Certificate of Excellence

37

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • 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

Certificate of Excellence

from $63 / night

$437 / week

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Responds fast!
avg. 3 hours 18 minutes

from $63 / night

(54) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $88 / night

$500 - $874 / week

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from $88 / night

9

Vacation apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Description The Convent. Rustico Toscano in the countryside with swimming pool The apartment is part of a complex of three apartments, with double bedroom, kitchen-dining room and bathroom with possibility of two additional beds. The apartment is independent and enjoys …see more

from $138 / night

$874 / week

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from $138 / night

14

Montepulciano Vacation home rental

Province of Siena / Montepulciano

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
An independent holiday home has a private garden surrounded by silence and stillness of the splendid Tuscan countryside, less than 2 km from the center of Montepulciano. The house is part of a complex that consists of three structures, each with a different reception ca …see more

from $100 / night

$695 / week

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from $100 / night

21

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
Holiday apartment separate entrance, located inside the medieval walls of Montepulciano (Si), double bedroom, single bedroom, living room / kitchen, bathroom for a total of 5 beds Week holiday. Possibility of short stay in the immediate vicinity, as well as to admire bu …see more

from $106 / night

$662 - $949 / week

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from $106 / night

(1) Excellent 

29

Vacation farmhouse in Montepulciano

Province of Siena / Montepulciano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 116 mi
  • Child friendly
  • Pet friendly
Our House is within the azienda agricola Podere San Pietro Montepulciano between Val di Chiana and the Val d'Orcia, dates back to the 14th century and has been renovated keeping the characteristics of the Tuscan farmhouse. Immersed in the green of olive trees and vines …see more

from $175 / night

$749 - $874 / week

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from $175 / night

(2) Excellent 

29

Vacation farmhouse in Montepulciano

Province of Siena / Montepulciano

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Casanova Woods is located in the heart of Val D'orcia, the landscape inscribed on Unesco's World Heritage List. The ancient ' Farm ', 1700 's farmhouse, has a wonderful view over the hills of Monticchiello and Pienza. The unique Montepulciano is only 5 km. Here time sto …see more

from $437 / night

$2,246 - $3,245 / week

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from $437 / night

5

B&b rental in Montepulciano

Province of Siena / Montepulciano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
Bellavista rooms are located in the heart of the historic center of Montepulciano at 30 metres from the main square in an ancient Palace of the recently renovated 500. The 10 rooms with their bathrooms have been completely renovated. The rooms are equipped with heating …see more

from $150 / night

$1,049 / week

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Responds fast!
avg. 3 hours 55 minutes

from $150 / night

(5) Very Good 

27

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • 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 $82 / night

$568 / week

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Responds fast!
avg. 3 hours 18 minutes

from $82 / night

21

Vacation b&b in Acquaviva di Montepulciano

Montepulciano / Acquaviva di Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • 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 $50 / night

$350 / week

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Responds fast!
avg. 3 hours 18 minutes

from $50 / night

26

Villa rental in Sant'Albino with swimming pool

Montepulciano / Sant'Albino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 115 mi
  • 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 $410 / night

$2,870 - $4,742 / week

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from $410 / night

(8) Very Good 

11

Montepulciano Vacation apartment rental

Province of Siena / Montepulciano

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • 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 $87 / night

$596 - $1,465 / week

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from $87 / night

5

Vacation b&b in Montepulciano

Province of Siena / Montepulciano

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
Bellavista rooms are located in the heart of the historic center of Montepulciano at 30 metres from the main square in an ancient Palace of the recently renovated 500. The 10 rooms with their bathrooms have been completely renovated. The rooms are equipped with heating …see more

from $125 / night

$874 / week

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Responds fast!
avg. 3 hours 55 minutes

from $125 / night

9

Vacation b&b rental

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
Open plan apartment of 55 sqm. located in the historical centre of Montepulciano (SI) to 250 m. from Piazza Grande. Furnished, with kitchenette, double bed, sofa bed can be used if necessary, and serve. Beautiful panoramic view over the Valdichiana and Trasimeno and M …see more

from $81 / night

$522 / week

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from $81 / 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 $137 / night

$745 / week

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Responds fast!
avg. 3 hours 10 minutes

from $137 / night

(1) Excellent 

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 $75 / night

$503 - $999 / week

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Responds fast!
avg. 1 hour 53 minutes

from $75 / night

18

Vacation home in Montepulciano

Province of Siena / Montepulciano

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
An independent holiday home has a private garden surrounded by silence and stillness of the splendid Tuscan countryside, less than 2 km from the center of Montepulciano. The house is part of a complex that consists of three structures, each with a different reception ca …see more

from $141 / night

$983 / week

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from $141 / night

10

Vacation home in Montepulciano

Province of Siena / Montepulciano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
Independent apartment located in the historical center of Montepulciano. The property was recently renovated and is located in a quiet and strategic location to reach the various places of interest: supermarket, mini-market, pharmacy, post office or at a cultural level …see more

from $138 / night

$749 / week

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from $138 / night

(1) Excellent 

12

Vacation home rental

Province of Siena / Montepulciano

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
A period residence in the heart of Montepulciano, a unique structure with frescoes and original furnishings. The apartment, located on the ground floor of the building, consists of 4 rooms with separate bathrooms. Full environment an exclusive renaissance garden. They a …see more

from $437 / night

$3,057 / week

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from $437 / night

(9) Very Good 

41

Vacation farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 $141 / night

$987 / week

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from $141 / night

(13) Excellent 

Certificate of Excellence

26

Vacation home in Montepulciano

Province of Siena / Montepulciano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 120 mi
  • Child friendly
  • Air conditioning
The house is located about 1.5 kilometers from the historic center of Montepulciano, in the tranquility and silence of the Tuscan countryside. House for exclusive use. The property was recently renovated in rustic style on the outside there is a beautiful garden. The ce …see more

Certificate of Excellence

from $113 / night

$749 - $924 / week

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from $113 / 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 $94 / night

$562 / week

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Responds fast!
avg. 41 minutes

from $94 / 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 $118 / night

$770 - $1,434 / week

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Responds fast!
avg. 1 hour 59 minutes

from $118 / night

(1) Excellent 

23

Vacation villa with shared pool in Montepulciano

Province of Siena / Montepulciano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • 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 $50 / night

$350 / week

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Responds fast!
avg. 3 hours 18 minutes

from $50 / 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 $94 / night

$624 - $1,180 / week

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Responds fast!
avg. 1 hour 53 minutes

from $94 / night

(2) Excellent 

17

Vacation farmhouse in Montepulciano

Province of Siena / Montepulciano

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 106 mi
  • Child friendly
  • Car not necessary
The apartment has two bedrooms one big bathroom and a service bath. The private entrance leads into a spacious lounge furnished with a authentic Tuscan table and chairs, a comfortable sofa set and coffee table and an open plan fire place very spacious and charmin …see more

from $178 / night

$1,247 - $1,248 / week

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from $178 / night

(11) Excellent 

Certificate of Excellence

52

Apartment rental in Montepulciano

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
This spacious apartment located in the historical centre of Montepulciano, at 100 metres from Piazza Grande, is located on the top floor of the historic Renaissance palace ' Fish Angelotti. From the large Windows you can admire the unique landscape of the Tuscan hills …see more

Certificate of Excellence

from $175 / night

$1,061 - $1,323 / week

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Responds fast!
avg. 3 hours 0 minutes

from $175 / night

(1) Excellent 

12

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Car not necessary
  • Pet friendly
The boutique housed on the first floor of a Renaissance palace, is situated in the historical center of Montepulciano, 20 meters from Piazza Grande. It enjoys a double exposure from which you can admire panoramic views of the main square and the Val d'Orcia. It consists …see more

from $200 / night

$1,146 / week

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from $200 / 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 $312 / night

$2,184 / week

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from $312 / night

(1) Excellent 

35

Vacation condo in Montepulciano

Province of Siena / Montepulciano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
Large apartment located in 2 levels attic of a building in the historic center of Montepulciano. At the entrance floor it offers 3 very large double bedrooms (one with a small living room with possibility of extra bed), a bathroom with shower, laundry / ironing room wit …see more

from $188 / night

$1,498 - $2,496 / week

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from $188 / night

10

Valiano Vacation apartment rental

Montepulciano / Valiano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • 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 $125 / night

$874 / week

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from $125 / night

7

Vacation apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
La Scala ( 2+2 posti letto) situato al primo piano, all'interno dell'Agriturismo Fontecastello, è costituito da un soggiorno con angolo cottura, divano letto matrimoniale e caminetto, una camera matrimoniale con letto aggiunto, una camera più piccola con letto da 120 cm …see more

from $94 / night

$961 / week

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from $94 / night