50 Best Montepulciano Apartment rentals on Holiday Lettings - Villas

Close

View larger map

Also consider

Valiano
14 properties
Acquaviva di Montepulciano
12 properties
Sant'Albino
12 properties
Abbadia di Montepulciano
7 properties

Montepulciano

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

286 Vacation rentals

Travelers going to Montepulciano are booking June dates now. Secure your vacation rental today and have the perfect trip.

(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 $87 / night

$479 - $2240 / week

Inquire View

from $87 / 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 $71 / night

$468 - $848 / week

Book View

from $71 / 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 w  …see more

from $77 / night

$327 - $566 / week

Book View

from $77 / 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 $77 / night

$533 / week

Book View

from $77 / 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 $82 / night

$490 / week

Book View

from $82 / 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 $153 / night

$924 / week

Book View

from $153 / 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
  • Ask about pets
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 $98 / night

$566 - $687 / week

Book View

from $98 / night

100

Vacation villa 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
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 $324 / night

$2263 - $3880 / week

Inquire View

from $324 / night

100

Vacation villa in Montepulciano

Province of Siena / Montepulciano

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 140 mi
  • Child friendly
ExteriorVilla Lavanda, this authentic Tuscan farmhouse lies amidst the beautiful countryside surrounding the town of Montepulciano (1.5km away)- woodland, extensive vineyards, bright flowers and olive groves. Montepulciano is a town rich in culture with plenty of histor  …see more

from $201 / night

$1401 - $2263 / week

Inquire View

from $201 / 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

$446 - $875 / week

Book View

from $71 / 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 $77 / night

$435 - $761 / week

Book View

from $77 / 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 $98 / night

$598 - $631 / week

Book View

from $98 / 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 $316 / night

$1740 - $2500 / week

Book View

from $316 / 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 si  …see more

from $296 / night

$2066 - $3696 / week

Book View

from $296 / night

(5) Excellent 

24

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly

 …see more

from $85 / night

$500 / week

Book View

from $85 / 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 $93 / night

$674 - $935 / week

Book View

from $93 / night

16

Montepulciano / Sant'Albino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from $87 / night

$544 - $772 / week

Book View

from $87 / night

(7) Very Good 

22

Province of Siena / Montepulciano

2 6 3 nights min

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

 …see more

from $98 / night

$577 / week

Book View

from $98 / night

100

Vacation villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
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 $755 / night

$3449 - $5604 / week

Inquire View

from $755 / 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 $125 / night

$761 - $944 / week

Book View

from $125 / 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 $109 / night

$522 - $653 / week

Book View

from $109 / 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

$549 - $1028 / week

Book View

from $87 / 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 $82 / night

$544 - $642 / week

Book View

from $82 / night

(5) Excellent 

20

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
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

Pricing unknown

Book View

Pricing unknown

100

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
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 $87 / night

$609 - $924 / week

Inquire View

from $87 / 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 $493 / night

$3449 - $6682 / week

Inquire View

from $493 / night

7

Montepulciano Vacation apartment rental

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • 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. One double bed room (king size), one bathroom and a living room w  …see more

from $77 / night

$327 - $566 / week

Book View

from $77 / 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 $153 / night

$979 / week

Book View

from $153 / night

12

Apartment rental in Valiano with swimming pool

Montepulciano / Valiano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The Terrarossa farm holiday resort is deep in the stunning hills around Montepulciano. It is part of an ancient country estate counting 130 acrwes land, where with respect for the land and its natural balance wheat, sunflowers and, above all, the vines for Vino Nob  …see more

from $164 / night

$816 - $1033 / week

Book View

from $164 / night

(13) 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 $97 / night

$510 - $575 / week

Book View

from $97 / night

32

Vacation villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Beautiful farmhouse placed in a panoramic position on the green hills covered by vineyards, olive groves and woods, only a few kilometres from Torrita di Siena and Montepulciano. Podere San Bono makes the most of a particularly advantageous position which matches the po  …see more

from $164 / night

$1142 - $2055 / week

Book View

from $164 / night

11

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

 …see more

from $77 / night

$479 / week

Book View

from $77 / 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

from $120 / night

$707 - $1087 / week

Inquire View

from $120 / night

18

Province of Siena / Montepulciano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from $87 / night

$609 / week

Book View

from $87 / night

6

Province of Siena / Montepulciano

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Private garden

 …see more

from $185 / night

$1087 / week

Book View

from $185 / 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

$760 - $1293 / week

Book View

from $130 / night

20

Vacation apartment rental

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets
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

$392 - $696 / week

Book View

from $93 / night

22

Montepulciano Vacation villa rental

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Our old farm dates back to Xv century, when it was the watermill of a noble family. Now entirely refurbished in a country very essential style it has a main house on 3 floors with 3 bedrooms and 2 kitchens and the old barn refurbished into 2 double large bedrooms wit  …see more

from $327 / night

$2283 / week

Book View

from $327 / 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

Book View

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 $55 / night

$381 / week

Book View

from $55 / night

1