50 Best Montepulciano Vacation rentals on Holiday Lettings - Villas

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Montepulciano

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291 Vacation rentals

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(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 w  …see more

from $75 / night

$321 - $557 / week

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from $75 / 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  …see more

from $86 / night

$471 - $2204 / week

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from $86 / 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 wit  …see more

from $81 / night

$482 / week

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from $81 / night

(48) 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 $75 / night

$428 - $749 / week

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from $75 / 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 $75 / night

$525 / week

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from $75 / 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 $70 / night

$439 - $861 / week

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from $70 / night

(10) Excellent 

26

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $91 / night

$664 - $920 / week

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from $91 / night

(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

 …see more

from $97 / night

$589 - $621 / week

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from $97 / 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 $128 / night

$748 - $1272 / week

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from $128 / night

(1) Excellent 

24

Montepulciano Vacation villa rental

Province of Siena / Montepulciano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The Poggio Golo holiday villa has been restored to its original splendour after long and careful renovation, giving you the possibility to savor the atmosphere of a holiday from past times in an old 17th century villa with original furniture and accessories. The well-tr  …see more

from $268 / night

$738 - $2621 / week

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from $268 / 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

 …see more

from $172 / night

$910 / week

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from $172 / 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 $86 / night

$541 - $1011 / week

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from $86 / 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, wher  …see more

from $123 / night

$749 - $929 / week

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from $123 / 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 $73 / night

$510 / week

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from $73 / night

8

Apartment rental in Montepulciano

Province of Siena / Montepulciano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Private garden
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. Two double bed rooms, one bathroom and a living room with kitchen  …see more

from $140 / night

$535 - $792 / week

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from $140 / night

27

Montepulciano Vacation villa rental

Province of Siena / Montepulciano

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 100 mi
  • 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 p  …see more

from $688 / night

$4814 - $8386 / week

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from $688 / 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 $75 / night

$525 / week

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from $75 / 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  …see more

from $123 / night

$615 - $1101 / week

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from $123 / 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 p  …see more

from $107 / night

$514 - $642 / week

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from $107 / 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

 …see more

from $311 / night

$1712 - $2460 / week

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from $311 / night

22

Province of Siena / Montepulciano

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 116 mi
  • Child friendly
  • Pet friendly

 …see more

from $150 / night

$1049 / week

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from $150 / night

14

Province of Siena / Montepulciano

1 3 Min stay varies

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

 …see more

from $81 / night

$535 - $632 / week

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from $81 / night

(11) 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 $96 / night

$449 - $566 / week

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from $96 / night

(1) Excellent 

21

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Suitable for children age 5+

 …see more

from $134 / night

$749 - $1049 / week

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from $134 / 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

$674 - $1236 / week

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from $118 / night

100

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
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

Pricing unknown

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Pricing unknown

(9) Very Good 

6

Montepulciano / Valiano

1 2 1 night min

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

 …see more

from $54 / night

$375 / week

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from $54 / night

13

Vacation chalet in Valiano

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Apartment with living-dining area, kitchen corner , 2 double bedroom , bathroom with shower. TV SAT, iron and iron board, freezer, oven, high chair.Beautiful farmhouse built with handmade 18th century bricks and surrounded by the peace and quiet of the hills aro  …see more

from $129 / night

$910 / week

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from $129 / 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 $214 / night

$1498 / week

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from $214 / night

13

Vacation apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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 Montep  …see more

Pricing unknown

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Pricing unknown

18

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $102 / night

$653 - $781 / week

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from $102 / night

23

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 $123 / night

$803 - $1059 / week

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from $123 / night

11

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

 …see more

from $75 / night

$471 / week

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from $75 / 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 farmhouse fattoriadiargiano dot it. In this beautiful Villa, were we live , at the second fl  …see more

from $54 / night

$375 / week

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from $54 / night

(2) Excellent 

25

Province of Siena / Montepulciano

2 4 3 nights min

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

 …see more

from $150 / night

$963 / week

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from $150 / night

99

Montepulciano / Abbadia di Montepulciano

5 10 Min stay varies

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

 …see more

from $535 / night

$3744 / week

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from $535 / night

(1) Excellent 

9

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 100 mi
  • Child friendly

 …see more

from $65 / night

$375 / week

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from $65 / night

(1) Excellent 

100

Vacation villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 180 mi
  • Swimming pool
  • Child friendly
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 $489 / night

$3423 - $6632 / week

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from $489 / night

(1) Excellent 

18

Province of Siena / Montepulciano

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from $70 / night

$460 - $835 / week

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from $70 / night

(15) Very Good 

97

Vacation farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

7 16 1 night min

  • 7 bedrooms
  • Sleeps 16
  • 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 gue  …see more

from $642 / night

$3744 / week

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from $642 / night