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  • Italy
  • Tuscany
  • Province of Siena
  • Montalcino
  • All locations
  • Castelnuovo dell'Abate (2)
  • Poggio alle Mura (12)
  • Sant'Angelo in Colle (1)
  • Val d'Orcia (20)

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153 Holiday homes

Travellers going to Montalcino are booking September dates now. Secure your holiday home today and have the perfect trip.

(13) Excellent 

1 / 20

Montalcino / Sant'Angelo in Colle

2 5 2 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Nearest beach 68 km; Suitable for children age 5+; Car essential;
 …see more

from £66 / night

£392 - £757 / week

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from £66 / night

1 / 12

Province of Siena / Montalcino

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £140 / night

£974 / week

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from £140 / night

(1) Excellent 

1 / 19

Suite d'Artista: Di Silvestre - Montalcino studio sleeps 2

Province of Siena / Montalcino

Studio 2 2 nights min stay

  • Studio
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Not suitable for children;
Suite d'Artista is a perfect place to enjoy a relaxing holiday combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming p  …see more

from £144 / night

£1005 / week

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from £144 / night

1 / 47

Villa Brunello - Castelnuovo dell'Abate villa sleeps 8

Montalcino / Castelnuovo dell'Abate

5 8 3 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Nearest beach 90 km; Swimming pool; Child friendly ;
This comfortable, cosy villa nestles on a sheltered incline among gently rolling hills. These are covered in Brunello wine-producing vineyards, which border the lower pool-terrace. The San Giuseppe winery, from which the house takes its name, is situated nearby. Wonderf  …see more

from £1166 / night

£6087 / week

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from £1166 / night

1 / 12

Province of Siena / Montalcino

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £105 / night

£696 / week

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from £105 / night

1 / 100

Borgo Brunello - Garden - Montalcino apartment sleeps 3

Province of Siena / Montalcino

2 3 1 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Nearest beach 85 km; Swimming pool; Child friendly ;
This stylishly decorated ground floor apartment opens up to a spacious living room with a charming kitchenette located towards the rear of the apartment. From here you can access the mezzanine above the kitchen, where a single bed is found. Through the corridor you will  …see more

from £122 / night

£827 / week

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from £122 / night

1 / 100

Borgo Brunello - Comfort 87 - Montalcino apartment sleeps 4

Province of Siena / Montalcino

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 85 km; Swimming pool; Child friendly ;
A charming 2 bedroom apartment at Borgo Brunello, like all the apartments it has been very recently decorated and boasts a lovely décor and excellent modern facilities. The 2 bedrooms are spacious doubles and there are also 2 bathrooms with a shower. The living r  …see more

from £218 / night

£1522 / week

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from £218 / night

1 / 12

Montalcino / Val d'Orcia

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
 …see more

from £105 / night

£696 / week

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from £105 / night

1 / 16

Farmhouse Podere Pienza - Val d'Orcia farmhouse sleeps 12

Montalcino / Val d'Orcia

5 12 3 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
The 300 m2 farmhouse has been beautifully restored. Split into 2 levels, the farmhouse has a huge open living room that has access to the terrace with outdoor furnishings for dining and relaxing. The farmhouse is adorned with fine Tuscan country furnishings.The farmhous  …see more

from £261 / night

£2000 / week

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from £261 / night

(3) Excellent 

1 / 18

Suite d'Artista: Basilè - Montalcino studio sleeps 2

Province of Siena / Montalcino

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
Suite d'Artista is a perfect place to enjoy a relaxing holiday combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming p  …see more

from £114 / night

£753 / week

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from £114 / night

1 / 19

Suite d'Artista: Riddell - Montalcino house sleeps 6

Province of Siena / Montalcino

2 6 2 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Suite d'Artista is a perfect place to enjoy a relaxing holiday, combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming  …see more

from £300 / night

£2100 / week

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from £300 / night

1 / 15

Montalcino / Val d'Orcia

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Nearest beach 80 km; Not suitable for children; Car essential;
 …see more

from £87 / night

£609 / week

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from £87 / night

1 / 21

Suite d'Artista: Botto & Bruno - Montalcino apartment sleeps 4

Province of Siena / Montalcino

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Suite d'Artista is a perfect place to enjoy a relaxing holiday combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming p  …see more

from £174 / night

£1218 / week

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from £174 / night

1 / 20

Casa Gallinaio - Val d'Orcia cottage sleeps 2

Montalcino / Val d'Orcia

1 2 7 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Nearest beach 70 km; Not suitable for children; Car advised;
"Vivo d'Orcia is not a place, it is a way of life..." The Castle of Vivo d'Orcia lies in the widespread Orcia valley in southern Tuscany, 2 hours from Florence, 1 hour from Siena, close to such cultural jewels as Pienza, Montalcino and Montepulciano,  …see more

from £90 / night

£627 - £783 / week

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from £90 / night

(1) Excellent 

1 / 37

House Ambasciatore: Overlooking the Orcia valley!

Montalcino / Val d'Orcia

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
"Vivo d'Orcia is not a place, it is a way of life..." The Castle of Vivo d'Orcia lies in the widespread Orcia valley in southern Tuscany, 2 hours from Florence, 1 hour from Siena, close to such cultural jewels as Pienza, Montalcino and Montepulciano, to name but a few.  …see more

from £157 / night

£1096 - £1492 / week

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from £157 / night

1 / 15

Montecaprili farmhouse: Pozzo apartment - Montalcino apartment sleeps 4

Province of Siena / Montalcino

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
Pozzo is an elegant and bright apartment of about 80m2 that can accommodate 4 persons. There are 2 bedrooms, a large bathroom with a shower cabinet and a nice living room with a fully equipped kitchen. The apartment is situated on the ground floor and suitable for handi  …see more

from £240 / night

£1566 / week

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from £240 / night

1 / 12

Province of Siena / Montalcino

1 1 1 night min stay

  • 1 bedroom
  • Sleeps 1
  • 1 night min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £66 / night

£457 / week

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from £66 / night

1 / 16

Gorgeous 2 bedroom villa in the Val d'Orcia region, features shared pool, private garden and barbecue

Montalcino / Val d'Orcia

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Located in the Val d'Orcia region south of Siena. This area has been declared a world heritage site by UNESCO. The house is located on a hill with panoramic views over the countryside and only 2 mins from the village of Montisi. Sitting out on your terrazza overloo  …see more

from £75 / night

£522 - £1127 / week

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from £75 / night

1 / 11

Suite Downtown - Casa Lapini - Montalcino apartment sleeps 4

Province of Siena / Montalcino

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Pet friendly;
A large (70 m²) and bright apartment set on the first floor, in the historical centre of Montalcino. There's a living room with sofa and TV at the entrance, a fully equipped kitchen that opens up into a small internal courtyard with barbecue, table and chairs. Up  …see more

from £131 / night

£861 / week

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from £131 / night

1 / 100

Borgo Brunello - Suite - Montalcino apartment sleeps 2

Province of Siena / Montalcino

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 85 km; Swimming pool; Child friendly ;
Our one-bedroom “suite” is an excellent choice for a couple on a romantic getaway or even a honeymoon. It is particularly elegant with a large bedroom including a 4-poster bed, a sleek bathroom with a bathtub, spacious living room with large sofa, dining are  …see more

from £166 / night

£1157 / week

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from £166 / night

1 / 19

Suite Artista: Cannavacciuolo - Montalcino apartment sleeps 3

Province of Siena / Montalcino

1 3 2 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Suite d'Artista is a perfect place to enjoy a relaxing holiday combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming p  …see more

from £127 / night

£883 / week

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from £127 / night

1 / 100

Borgo Brunello - Deluxe 66 - Montalcino apartment sleeps 6

Province of Siena / Montalcino

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Nearest beach 85 km; Swimming pool; Child friendly ;
One of the larger apartments at 84sqm, it can comfortably accommodate up to 6 in 3 double bedrooms. It is very attractive in style with elegant neutrals, wooden beams and a pretty pastel blue as a contrasting colour. Everything down to the finest details has been taken  …see more

from £296 / night

£2044 / week

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from £296 / night

(28) Excellent 

1 / 26

Fonte Aulente Montalcino - Val d'Orcia farmhouse sleeps 5

Montalcino / Val d'Orcia

2 5 3 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored and surrounded by beautiful garden-park, 2 km from Montalcino, in a panoramic position with amazing views over the Tuscan hills. The apartment is a part of the old farmhouse, with its own ent  …see more

from £118 / night

£822 / week

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from £118 / night

1 / 24

Montalcino / Val d'Orcia

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £200 / night

£1400 / week

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from £200 / night

(1) Excellent 

1 / 12

villa in esclusiva con piscina - Val d'Orcia villa sleeps 7

Montalcino / Val d'Orcia

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
Villa of 250 square meters. with fully equipped kitchen, living room, hall and bathroom on the ground floor. On the first floor three large bedrooms each with private bathroom and living room. TV flat screen in all room and living.Garden of 5000 sqm with swimming pool 4  …see more

from £249 / night

£1740 - £2087 / week

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from £249 / night

1 / 33

Province of Siena / Montalcino

2 5 2 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
 …see more

from £131 / night

£914 / week

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from £131 / night

1 / 15

Montalcino / Val d'Orcia

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 80 km; Not suitable for children; Car essential;
 …see more

from £79 / night

£548 / week

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from £79 / night

(7) Excellent 

1 / 24

Charming Tuscan villa with pool, Montalcino, Siena

Montalcino / Val d'Orcia

4 9 7 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
One of three unique and charming apartments in a XVI century villa situated in the wonderful senese countryside a few km's from Montalcino, in the natural park of the Val d' Orcia, a precious architectural and natural context.Here you will feel embraced by the  …see more

from £249 / night

£1740 - £2092 / week

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from £249 / night

1 / 22

Province of Siena / Montalcino

3 8 2 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Child friendly ; Ask about pets;
 …see more

from £183 / night

£1096 / week

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from £183 / night

1 / 10

San Quirico D'Orcia holiday apartment

Province of Siena / Montalcino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Car essential; No pets allowed;
Comfortable fully renovated apartment in San Quirico D'Orcia at 3 mins walk from the village center in one of the most scenic area of Tuscany and Word Heritage site.The apartment is on the first floor of a 2 apartments building, in a quiet area.Spacious living room  …see more

from £60 / night

£417 / week

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from £60 / night

1 / 50

Casa Brunello di Montalcino - Montalcino apartment sleeps 6

Province of Siena / Montalcino

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Suitable for children age 5+; No pets allowed;
Enjoy winelovers' paradise in Montalcino from the beautifully renovated and spacious apartment - Casa Brunello di Montalcino - in the 17th century building with some nice original pieces, combining the traditional Tuscan countryside look with modern high-quality fu  …see more

from £283 / night

£1740 - £2435 / week

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from £283 / night

1 / 5

Montalcino / Val d'Orcia

3 8 3 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £105 / night

£731 / week

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from £105 / night

(1) Excellent 

1 / 25

Province of Siena / Montalcino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £227 / night

£1672 - £2194 / week

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from £227 / night

1 / 100

Brunello - Montalcino villa sleeps 8

Province of Siena / Montalcino

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
Exteriors The fragrant smell of 10 hectares of vineyards and olive groves envelope this villa for rent in Tuscany, Italy, which at present shows its best face, thanks to the devoted restoration it underwent.From the panoramic pool guests will envisage before leaving on  …see more

from £522 / night

£3653 - £4957 / week

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from £522 / night

(4) Excellent 

1 / 21

Comfort and style in the Siena counrtyside,

Montalcino / Val d'Orcia

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
One of three unique and charming apartments in a XVI century villa situated in the wonderful Siena countryside a few kms from Montalcino, in the natural park of the Val d'Orcia, a precious architectural and natural context.Here you will feel embraced by the fascina  …see more

from £237 / night

£1653 - £2087 / week

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from £237 / night

1 / 21

Province of Siena / Montalcino

6 12 2 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 2 nights min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £435 / night

£3044 / week

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from £435 / night

1 / 20

Argiano - 17314001 - Montalcino farmhouse sleeps 10

Province of Siena / Montalcino

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Ask about pets;
Fontanelle is without doubt one of our loveliest Tuscan properties. It is located to the west of Montalcino, an area renowned for its beauty and for its wines, especially the famous Brunello di Montalcino. The property is in a spectacular position, surrounded by  …see more

from £726 / night

£5079 - £8366 / week

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from £726 / night

1 / 16

Montecaprili farmhouse: Archi apartment - Montalcino apartment sleeps 6

Province of Siena / Montalcino

2 6 2 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
Archi is a splendid independent apartment of about 130m2 which can host 4+2 persons. It's composed of 2 bedrooms (1 double + 1 twin), 2 bathrooms (1 with bathtub and shower + 1 with shower) and a huge open plan that serves as living room with 2 large couches (1 of  …see more

from £331 / night

£2174 / week

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from £331 / night

1 / 100

Borgo Brunello - Deluxe 01 - Montalcino apartment sleeps 6

Province of Siena / Montalcino

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Nearest beach 85 km; Swimming pool; Child friendly ;
The second of the two 3 bedroom apartments, it is just as lovely and light and bright. It is laid out over two floors so the ground floor bedrooms have direct access onto the estate´s stunning grounds. Also on the lower level is the very large living space consist  …see more

from £296 / night

£2044 / week

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from £296 / night

1 / 20

Villa Bandini - Val d'Orcia villa sleeps 8

Montalcino / Val d'Orcia

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 95 km; Swimming pool; Child friendly ;
Villa Bandini is located only 300 meters from the hamlet of Lucignano d’Asso on top of a hill on the border between the Val d’Orcia and the Sienese clay hills. Lucignano d’Asso is a medieval ancient hamlet which, since the XV century, has belonged to the Piccolomi  …see more

from £335 / night

£2344 - £4474 / week

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from £335 / night

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