List your home
Apply filters
£ to

151 Holiday homes in Montepulciano

Reset search

Show results on map

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
Rome
2,420 properties
Florence
947 properties
Trapani
498 properties
Venice, Veneto
480 properties
Amalfi Coast
457 properties
Cortona
428 properties
Lucca
428 properties
Palermo
383 properties
Sorrento, Campania
350 properties
Cefalu
310 properties
San Gimignano
296 properties
Greve in Chianti
267 properties
Taormina
260 properties
Syracuse
250 properties
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
151 Results  |  
24 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £80 /night

£560 / week

View

Key info:

  • Nearest beach 120 km
  • Suitable for children of all ages
  • No pets allowed
These quaint apartments are perfect for guests who want a holiday full of complete relaxation, while enjoying terrific views of Montepulciano and the surrounding valley. It is in the perfect location to discover the cultural and historical heritage o  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £446 /night

£3120 - £5200 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Celiaandnbsp;is an extraordinary , fully restored Tuscan Villa rental located in Castelmuzio, Siena.andnbsp;It is a beautiful villa ofandnbsp;400 square metersandnbsp;and can easily accommodateandnbsp;8 people. Villa Celia is comprised ofandnbsp;three  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £677 /night

£4734 - £5118 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Luxury holiday house for 16 persons, with swimming pool , in Chiusi - Chianciano  …see more

Featured properties

16 Photos

Villa | 4 Bedrooms | sleeps 7

2 Nights min stay

Add to shortlist

from £405 /night

£2833 - £4723 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Villa La Residenza is not just a rental villa; it is a home. The owner's have collected a unique mix of antiques and modern furnishings from all over the world, aiming to blend the old and new with a sense of style and comfort.  …see more

13 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £400 /night

£2800 - £3800 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Casa Romanzaandnbsp;boasts a lovely location on the hilltops of Castelmunzio, a small and delightful village in the undulating Tuscan countryside. andnbsp;Accommodating up toandnbsp;10 persons on two floors, Casa Romanza includes a vast swimming pool and the most  …see more

12 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £567 /night

£3968 - £6720 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • May take pets – please enquire
Villa / Farmhouse / Home in Cortona with 8 bedrooms sleeps 16  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £229 /night

£1600 - £1704 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Montepulciano with 3 bedrooms sleeps 6  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 2

5 Nights min stay

Add to shortlist

from £286 /night

£2000 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
andlt;bandgt;Apartment Cherylandlt;/bandgt; is situated in the andnbsp;ancient villa of the medieval period, a short distance from Montepulciano and a few kilometers from the famous and beautiful southern Siena cities like Pienza, Cortona, Montefollonico and obviously  …see more

15 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £93 /night

£647 - £878 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This apartment is located in a farm-turned-holiday home built in 1878, in the province of Montepulciano, which is famous for its vineyards. The ancient farm has been totally restored and contains four beautiful apartments. It has its own garden. Today the farm is rec...  …see more

20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £252 /night

£1760 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Moscatella is a characteristic three-story age-old farm house surrounded by vineyards and olive groves. It sleeps six people. From Casa Moscatella you will enjoy a fascinating view of Montepulciano and of the hills of Valdichiana  …see more

20 Photos

Villa | 12 Bedrooms | sleeps 24

7 Nights min stay

Add to shortlist

from £2160 /night

£15120 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
The villa is elegant and majestic in its eighteenth century form, the location is stunning with excellent furnishing and a beautiful garden, a welcoming and cozy atmosphere in a perfect Italian style Villa.  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £96 /night

£672 - £784 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Palazzoandnbsp;Apartment inandnbsp;Montepulciano Italyandnbsp;is distinctly raunchy and practically chic in its own way.andnbsp; Set up on theandnbsp;topmost floor, this has the power to prolong the stay of any occupier who comes to abide in by giving the best view  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 20

3 Nights min stay

Add to shortlist

from £286 /night

£2000 - £6646 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Artisti,andnbsp;Luxury Tuscany Wedding Villa Rental sleepsandnbsp;20 People.This spacious villa hasandnbsp;two floorsandnbsp;of living quarters where Guests can freely relax in the shade of oak and cypress trees in the large garden surrounding the house.andnbsp;  …see more

17 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £438 /night

£3060 - £4151 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Casa Olive enjoys the peace and beauty of the Tuscan countryside, but with the convenience of a location within village of Castelmuzio. The large grounds include a private infinity swimming pool, and secluded gardens with dramatic views.  …see more

13 Photos

Villa | 5 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £141 /night

£981 - £2083 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Holiday house for 13 persons, with swimming pool , in Cortona  …see more

20 Photos

Villa | 1 Bedroom | sleeps 10

5 Nights min stay

Add to shortlist

from £343 /night

£2400 - £3200 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Romanzaandnbsp;is a large villa for rent in Tuscany with over 100 years of history.andnbsp;The villa can accommodate up toandnbsp;10 peopleandnbsp;in its lovely duplex apartment situated on theandnbsp;first and second floor of the property.andnbsp;  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £144 /night

£1008 - £1232 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Recently renovated, 110 square metre apartment for 4 people situated in the main piazza of the beautiful village of Montepulciano with stunning views of both the piazza and of the surrounding countryside.andnbsp; 2 bedroomsandnbsp;as 1 double andandnbsp;1  …see more

11 Photos

Farmhouse | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £146 /night

£1020 - £2007 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Foiano Della Chiana with 5 bedrooms sleeps 10  …see more

24 Photos

Farmhouse | 7 Bedrooms | sleeps 16

3 Nights min stay

Add to shortlist

from £538 /night

£3760 - £5760 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Montepulciano with 7 bedrooms sleeps 16  …see more

12 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £572 /night

£4000 - £4400 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Montepulciano with 8 bedrooms sleeps 16  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

5 Nights min stay

Add to shortlist

from £290 /night

£2028 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Casa Gavinaandnbsp;is a Tuscan farmhouse rental situated in a 250 acres estate surrounded by wildlife in San Miniato, Pisa.andnbsp;The farmhouse is an independent villa ofandnbsp;130 square metersandnbsp;and can comfortably sleepandnbsp;6 persons.andnbsp; Casa Gavina  …see more

12 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £572 /night

£4000 - £4400 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Montepulciano with 8 bedrooms sleeps 16  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 18

2 Nights min stay

Add to shortlist

from £1179 /night

£8250 - £16250 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
The exquisite villa is located in Contignano surrounded by spectacular views of rolling clay hills and countryside. The villa sleeps up to 19 in 8 very spacious bedrooms, 2 twins, 5 doubles and a lofted bedroom containing a sofa bed, a twin and a double bed  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £152 /night

£1064 - £2964 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Villa Riccoandnbsp;is a charmingly restored farmhouse sits immersed in cultivated fields with breathtaking views of the Tuscan countryside.andnbsp; The villa hasandnbsp;two floors. On theandnbsp;ground floorandnbsp;aandnbsp;large arch wood and glass doorandnbsp;step  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 14

5 Nights min stay

Add to shortlist

from £480 /night

£3360 - £4704 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
A remarkable villa, replete with ancient history, situated in Montepulciano,andnbsp;Villa Dal Pinetto, offers impressive views of vineyards, olive groves, neighbouring towns including Cortona and Chianciano Terme, an ancient town with thermal baths situated around its  …see more

10 Photos

Farmhouse | 5 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £131 /night

£917 - £1954 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 5 bedrooms sleeps 13  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £69 /night

£482 - £833 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Montepulciano  …see more

22 Photos

Villa | 6 Bedrooms | sleeps 12

rentals_reviews_rating_2 

2 Nights min stay

Add to shortlist

from £495 /night

£3461 - £5100 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Six bedroom historical villa in the countryside of Montepulciano, a vibrant city at the heart of the Siena region of Tuscany.  …see more

17 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £522 /night

£3648 - £4576 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
A stunning residence built into the ancient city walls of the medieval and atmospheric town of Castelmuzio, BORGO ANTICO is the epitome of style and grace. Situated in the tiny but charming Piazza San Bernardino in the town's historic center  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 16

1 night min stay

Add to shortlist

from £560 /night

£3920 - £4640 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Ciliegia is a charming three-story historical villa surrounded by a wonderful age-old park. It sleeps 16 people. It is appoximately 600 square meters (6460 square feet). It features a private swimming pool, a private garden and winter heating  …see more

15 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £156 /night

£1090 - £2140 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Holiday house for 10 persons, with swimming pool , in Cortona  …see more

21 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £60 /night

£415 - £686 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This apartment is located in a holiday home built in 1878, in the province Montepulciano, famous for its vineyards. This antique farm has been totally restored and contains four beautiful apartments. The house has its own garden. Today the farm is recognized as a his...  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

5 Nights min stay

Add to shortlist

from £669 /night

£4680 - £5720 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Chiaraandnbsp;is a lovely Tuscan rental located in Montepulciano, Siena. The villa has been completely furnished andnbsp;and restored with both modern and antique pieces. This holiday villa is set on a beautiful landscape surrounded by fruit trees and olive  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £515 /night

£3605 - £6798 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Villa Zingo is an exception idyllic Tuscan retreat nestled in the charming town Chiamciano.  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £286 /night

£2000 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Cottage Brettinaandnbsp;andnbsp;is a Tuscan cottage rental located at Montepulciano, Siena surrounded by vineyards, cypress and walnut trees. Thisandnbsp;80 square meterandnbsp;house can accommodateandnbsp;4 peopleandnbsp;for stay. The Cottage Brettina has  …see more

16 Photos

Villa | 9 Bedrooms | sleeps 18

2 Nights min stay

Add to shortlist

from £1179 /night

£8250 - £16250 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annex. It is surrounded by breathtaking views over the Italian countryside  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £589 /night

£4120 - £7621 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Contemporary five bedroom property with three doubles and two twin bedrooms. The villa is situated in the wonderful province of Siena, rich in history and culture.  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

Add to shortlist

from £101 /night

£705 - £1448 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
3-room apartment 45 m2: living/dining room with 1 sofa bed and TV. 1 double bedroom. 1 room with 2 beds. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Recently renovated in full respect of Tuscan tradition, this old farmhouse situated in a panoramic position  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £84 /night

£588 - £1217 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
2-room apartment 40 m2: living room with 1 double sofa bed and TV. 1 double bedroom. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Recently renovated in full respect of Tuscan tradition, this old farmhouse situated in a panoramic position has managed to prese  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £84 /night

£588 - £1217 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
2-room apartment: living/dining room with 1 double sofa bed, satellite-TV and air-conditioning. 1 room with 1 french bed. Kitchenette. Bath/bidet/WC. Farmhouse 'Poggio Olivo'. In the resort, in a quiet position. For shared use: swimming pool (12 x 6 m,  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

Add to shortlist

from £101 /night

£705 - £1448 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
3-room apartment: living/dining room with 1 sofa bed, satellite-TV and air-conditioning. 1 room with 2 beds. Room with 1 french bed. Kitchenette. Bath/bidet/WC. Farmhouse 'Poggio Olivo'. In the resort, in a quiet position. For shared use: swimming pool  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £84 /night

£588 - £1217 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
2-room apartment 40 m2: living room with 1 double sofa bed and TV. 1 double bedroom. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Recently renovated in full respect of Tuscan tradition, this old farmhouse situated in a panoramic position has managed to prese  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £69 /night

£483 - £971 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
1-room apartment 25 m2: living/dining room with 1 french bed and TV. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Recently renovated in full respect of Tuscan tradition, this old farmhouse situated in a panoramic position has managed to preserve its original  …see more

13 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £84 /night

£588 - £1217 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
2-room apartment 40 m2: living room with 1 double sofa bed and TV. 1 double bedroom. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Recently renovated in full respect of Tuscan tradition, this old farmhouse situated in a panoramic position has managed to prese  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £69 /night

£480 / week

View

Key info:

  • Nearest beach 120 km
  • Suitable for children of all ages
  • No pets allowed
These quaint apartments are perfect for guests who want a holiday full of complete relaxation, while enjoying terrific views of Montepulciano and the surrounding valley. It is in the perfect location to discover the cultural and historical heritage o  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £131 /night

£917 - £1954 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
charming accommodation sleeps 13 people, so it is perfect for large families and is located in Tuscany Italy. This property is ideal if you seek a unique experience. The villa offers: a swimming Pool, a pet friendly space .  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £69 /night

£480 / week

View

Key info:

  • Nearest beach 120 km
  • Suitable for children of all ages
  • No pets allowed
These quaint apartments are perfect for guests who want a holiday full of complete relaxation, while enjoying terrific views of Montepulciano and the surrounding valley. It is in the perfect location to discover the cultural and historical heritage o  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £69 /night

£480 / week

View

Key info:

  • Nearest beach 120 km
  • Suitable for children of all ages
  • No pets allowed
These quaint apartments are perfect for guests who want a holiday full of complete relaxation, while enjoying terrific views of Montepulciano and the surrounding valley. It is in the perfect location to discover the cultural and historical heritage o  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £132 /night

£924 - £1540 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Charming Historic House with swimming pool in southern Tuscany near Montepulciano have a taste of Tuscany with Yourtuscanvilla!  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

14 Nights min stay

Add to shortlist

from £109 /night

£760 - £960 / week

View

Key info:

  • Suitable for children of all ages
  • No pets allowed
Mansarda and Padronale are two luxury flats located in the town of Montepulciano, charming decoration, breath taking views  …see more