50 Best Montepulciano Apartment rentals on Holiday Lettings - Villas

Close

View larger map

Also consider

Valiano
15 properties
Acquaviva di Montepulciano
11 properties
Sant'Albino
11 properties
Abbadia di Montepulciano
8 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

310 Vacation rentals

(13) Very Good 

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 $94 / night

$516 - $2416 / week

Inquire View

from $94 / 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 $129 / night

$807 - $1155 / week

Book View

from $129 / night

(50) 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 $83 / night

$470 - $821 / week

Book View

from $83 / night

(8) Very Good 

48

Montepulciano Vacation home rental

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
Tuscan-style villa, very close to Montepulciano's historic centre within walking distance. Located on the mezzanine level, is well decorated and features large terraces overlooking the countryside and the beautiful view of the city of Montepulciano. The House (approx. 1 …see more

from $94 / night

$645 - $704 / week

Book View

from $94 / night

(12) 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
  • Child friendly
  • Air conditioning
  • Pet friendly
The Corolline is located about 1.5 km from the historic centre of Montepulciano, immersed in the tranquillity and silence of the Tuscan countryside. The structure has been recently renovated, rustic style, outside is a beautiful garden. The central location is strategi …see more

Certificate of Excellence

from $94 / night

$704 - $1009 / week

Book View

from $94 / night

(16) Excellent 

Certificate of Excellence

25

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Car not necessary
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 stories and my f …see more

Certificate of Excellence

from $105 / night

$480 - $562 / week

Book View

Responds fast!
avg. 2 hours 29 minutes

from $105 / 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 $83 / night

$352 - $610 / week

Book View

from $83 / night

(2) 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 $71 / night

$411 / week

Book View

from $71 / night

(10) Very Good 

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 $135 / night

$763 - $1132 / week

Book View

from $135 / night

(23) 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 $140 / night

$809 - $1407 / week

Book View

Responds fast!
avg. 2 hours 29 minutes

from $140 / 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 $135 / night

$821 - $1018 / week

Book View

Responds fast!
avg. 2 hours 16 minutes

from $135 / 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 $106 / night

$610 - $742 / week

Book View

Responds fast!
avg. 2 hours 16 minutes

from $106 / 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 $71 / night

$475 - $945 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

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 $193 / night

$1349 - $2991 / week

Inquire View

from $193 / night

7

Vacation apartment with shared pool in Valiano

Montepulciano / Valiano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
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 Nobil …see more

from $176 / night

$1068 / week

Book View

from $176 / night

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
Casa vacanze indipendente dotata di giardino privato immerso nel silenzio e nella calma della splendida campagna toscana a meno di 2 chilometri dal centro storico di Montepulciano. La villetta fa parte di un complesso che si compone di altre tre strutture, ognuna con ca …see more

from $124 / night

$862 / week

Book View

from $124 / night

12

Vacation home rental

Province of Siena / Montepulciano

4 6 1 night min

  • 4 bedrooms
  • Sleeps 6
  • 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 $352 / night

$2463 / week

Book View

from $352 / 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 $319 / night

$2229 - $3401 / week

Book View

from $319 / 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 guests may spen …see more

from $704 / night

$4105 / week

Book View

from $704 / night

(1) Excellent 

29

Vacation farmhouse in Montepulciano

Province of Siena / Montepulciano

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 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 $341 / night

$1877 - $2698 / week

Book View

from $341 / night

(9) Very Good 

6

Valiano Vacation home rental

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Pet friendly
Small detached house with a ground floor of 22 square meters with living room and fitted kitchen and master bedroom on the first floor with bath. A Valiano, quiet old town in a strategic position to visit the city of art and nature: Montepulciano, Siena, Cortona, Lake T …see more

from $59 / night

$411 / week

Book View

from $59 / night

(5) 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 $83 / night

$575 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

from $83 / night

11

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Grazioso alloggio, in centro città ma in zona tranquilla, accessibile all'arte, storia, cultura, all'ottimo cibo e ai vini pregiati, con splendide viste panoramiche a due passi. Ti piacerà il mio alloggio per come è stato ristrutturato e arredato, per il confort, l'inti …see more

from $83 / night

$516 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from $83 / 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 $88 / night

$587 - $1109 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from $88 / 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 $235 / night

$1642 / week

Book View

from $235 / 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 $42 / night

$288 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

from $42 / night

(2) Excellent 

25

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 $165 / night

$1056 / week

Book View

from $165 / night

55

Vacation farmhouse with shared pool in Valiano

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
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 $94 / night

$997 - $1290 / week

Book View

from $94 / night

27

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
This Charming house is located in the countryside surrounding Montepulciano close to the historical centre of the town. Agriturismo Raggio di Sole has been recently restructured and it offers the hospitality of a farmhouse that provides all the comforts of a modern ho …see more

from $141 / night

$986 / week

Book View

from $141 / 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 $112 / night

$728 - $1355 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from $112 / night

15

Sant'Albino Vacation home rental

Montepulciano / Sant'Albino

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
Nice apartment in S. Albino (3 kilometers from Montepulciano, and 500 meters from the Terme di Montepulciano) Large entrance hall, lounge with kitchenette, two bedrooms, bathroom, utility room and balcony. In 5 minutes by car you reach Montepulciano and Chianciano Terme …see more

from $71 / night

$493 / week

Book View

from $71 / night

(1) Excellent 

18

Vacation apartment rental

Province of Siena / Montepulciano

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • 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 $77 / night

$505 - $915 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from $77 / 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 Montepulciano (D.O …see more

Pricing unknown

Book View

Pricing unknown

(10) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $83 / night

$575 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

from $83 / night

(10) 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 $165 / night

$997 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from $165 / night

(1) Very Good 

18

B&b rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • 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 $47 / night

$329 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

from $47 / 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 $141 / night

$997 / week

Book View

from $141 / 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 $352 / night

$2463 - $4222 / week

Inquire View

from $352 / night

(1) Excellent 

22

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 $165 / night

$704 - $880 / week

Book View

from $165 / night

34

Sant'Albino Vacation villa rental

Montepulciano / Sant'Albino

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves. It has been turned into a residence of refined charm that retains an atmosphere of informal welcome. The landscape and environment of Montepulciano are amo …see more

from $537 / night

$3753 - $7271 / week

Inquire View

from $537 / night