50 Best Montepulciano Apartment rentals on Holiday Lettings - Villas

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Valiano
37 properties
Gracciano
28 properties
Acquaviva di Montepulciano
26 properties
Bivio di San Biagio
23 properties
Sant'Albino
14 properties
Abbadia di Montepulciano
7 properties

Montepulciano

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4,842 Vacation rentals

(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 $116 / night

$581 / week

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from $116 / 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 $163 / night

$812 / week

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from $163 / night

(11) Excellent 

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

from $58 / night

$406 / week

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Responds fast!
avg. 3 hours 20 minutes

from $58 / night

(2) Excellent 

29

Vacation farmhouse in Montepulciano

Province of Siena / Montepulciano

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • 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 $406 / night

$2,086 - $3,013 / week

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from $406 / 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 $290 / night

$2,028 / week

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from $290 / 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 $70 / night

$475 - $881 / week

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avg. 1 hour 48 minutes

from $70 / night

(15) Excellent 

34

Vacation home in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 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

from $82 / night

$696 - $893 / week

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from $82 / night

(56) 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 $116 / night

$697 - $813 / week

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Responds fast!
avg. 3 hours 39 minutes

from $116 / 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 $132 / night

$924 / week

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from $132 / night

(3) Excellent 

9

Montepulciano Vacation townhouse accommodation

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 100 mi
  • Child friendly
Just two steps away from Montepulciano's main square, Piazza Grande, recently renovated apartment in the historic centre of the town called "Pearl of 500 ' for its treasures dating back to the Renaissance. Beautiful sunset views from the balcony, the hills of Val d'Orci …see more

from $82 / night

$464 - $638 / week

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from $82 / 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 $140 / night

$813 / week

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from $140 / 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 $111 / night

$720 - $1,341 / week

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Responds fast!
avg. 1 hour 31 minutes

from $111 / 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 $128 / night

$812 / week

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Responds fast!
avg. 3 hours 30 minutes

from $128 / 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 $87 / night

$522 / week

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Responds fast!
avg. 41 minutes

from $87 / 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 $82 / night

$488 - $755 / week

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from $82 / night

32

Valiano Vacation farmhouse rental

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
Circondato da vigne e ulivi, fra le colline della Val di Chiana che disegnano il suggestivo paesaggio senese, l'agriturismo a conduzione familiare è un antico casolare del '700 al confine tra Toscana e Umbria, ideale per raggiungere importanti mete come Montepulciano, P …see more

from $87 / night

$522 - $754 / week

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from $87 / night

38

Vacation villa rental

Montepulciano / Bivio di San Biagio

4 9 3 nights min

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min
  • Child friendly
  • Pet friendly
Beautiful farm in Montepulciano, immersed in the Sienese countryside. Four bedrooms, a kitchen and a small kitchen, three bathrooms, a gazebo. 09 comfortable seats bed. The house, on the first floor, a kitchen area with fireplace, two double bedrooms and a children's ro …see more

from $151 / night

$1,055 / week

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from $151 / night

40

Vacation farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights 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 $163 / night

$927 / week

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Responds fast!
avg. 3 hours 30 minutes

from $163 / night

(13) 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 $134 / night

$812 - $1,006 / week

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Responds fast!
avg. 3 hours 44 minutes

from $134 / night

(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 $105 / night

$603 - $733 / week

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Responds fast!
avg. 3 hours 44 minutes

from $105 / 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 $116 / night

$812 / week

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from $116 / night

(4) Excellent 

24

Vacation farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $672 / night

$2,666 - $4,404 / week

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from $672 / 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 $70 / night

$470 - $933 / week

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Responds fast!
avg. 2 hours 10 minutes

from $70 / 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 $134 / night

$933 / week

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from $134 / night

(13) Excellent 

19

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
The Palace welcomes you in the heart of Montepulciano and provides you the opportunity to enjoy a relaxing stay in order to explore the beauties of Tuscany. Old apartment in the historical center of Montepulciano recently restored. Opposite Palazzo Cervini and a few met …see more

from $134 / night

$801 - $1,167 / week

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from $134 / night

(11) Excellent 

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

from $163 / night

$985 - $1,229 / week

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Responds fast!
avg. 2 hours 37 minutes

from $163 / 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 $429 / night

$2,608 / week

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Responds fast!
avg. 3 hours 30 minutes

from $429 / night

11

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Car not necessary
Nice accommodation in the city center but in quiet area, accessible to art, history, culture, great food and fine wines, with stunning panoramic views at your doorstep. My accommodation you will like it as it has been restored, furnishing, comfort and intimacy, the quie …see more

from $82 / night

$510 / week

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from $82 / night

(24) 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 $134 / night

$752 - $1,390 / week

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Responds fast!
avg. 1 hour 38 minutes

from $134 / 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 $47 / night

$325 / week

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Responds fast!
avg. 3 hours 20 minutes

from $47 / 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 $76 / night

$528 / week

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Responds fast!
avg. 3 hours 20 minutes

from $76 / 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 $82 / night

$557 - $1,370 / week

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from $82 / 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 $47 / night

$325 / week

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Responds fast!
avg. 3 hours 20 minutes

from $47 / night

(1) Excellent 

41

Sant'Albino Vacation home rental

Montepulciano / Sant'Albino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
our farmhouse is completely independent, so as to guarantee privacy, intimacy and peace. There are three bedrooms, a spacious kitchen with working fireplace! a very spacious bathroom with dressing room with two sinks, you can cook on the grill and conviverete in the gar …see more

from $115 / night

$927 - $1,171 / week

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from $115 / night

(3) Excellent 

16

Montepulciano Vacation b&b rental

Province of Siena / Montepulciano

6 12 2 nights min

  • 6 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Podere raffaello, located in Val di Chiana, in the middle of Tuscany, coircondato from the countryside, lipu oasis of Montepulciano lake, 6km away from the pearl of the Renaissance. Two hectares of Italian garden, cared for with swimming pool, relaxation areas, car park …see more

from $198 / night

$1,381 / week

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from $198 / night

22

Vacation apartment rental

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
Apartment located in the Italian region of Tuscany in Montepulciano Via Iris Origo n 100 with panoramic views over the Chiana Valley just 5 minutes from the historic center, within walking distance of all amenities and the typical Tuscan restaurants. Montepulciano is th …see more

from $93 / night

$418 - $742 / week

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Responds fast!
avg. 1 hour 8 minutes

from $93 / night

(5) Excellent 

24

Montepulciano Vacation apartment rental

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
Separate apartment, a mix of modern and traditional elements of Tuscany. Functional facilities, warm in winter, cool in summer. 1 bedroom, 1 bathroom, sleeps 4 people. Parking, linens and towels, free wifi, garden. Strategic location and easy to reach. The part of Tusca …see more

from $91 / night

$533 / week

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from $91 / night

(17) Excellent 

36

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 $116 / night

$649 - $2,387 / week

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from $116 / night

33

Vacation apartment rental

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 115 mi
  • 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, …see more

from $135 / night

$941 / week

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from $135 / night

7

Vacation home in Montepulciano

Province of Siena / Montepulciano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
Lovely townhouse in the city center consists of lounge with fireplace and bathroom on the ground floor, two double rooms and a bathroom on the first floor. Located next to the church of St. Anthony. Nearby restaurants, shops and beautiful panoramic views. Ideal for coup …see more

from $151 / night

$780 / week

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from $151 / night