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92 Holiday homes

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

(5) Very Good 

1 / 23

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Child friendly ; Ask about pets; Private garden;
 …see more

from £74 / night

£479 - £574 / week

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from £74 / night

(15) Very Good 

1 / 97

7 bedroom Tuscan farmhouse near rennaissance town of Montepulciano, features include jacuzzi, private garden and pool

Province of Siena / Montepulciano

7 16 1 night min stay

  • 7 bedrooms
  • Sleeps 16
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car essential;
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  …see more

from £522 / night

£3044 / week

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from £522 / night

1 / 12

Agriturismo Terrarossa 4px - Valiano apartment sleeps 4

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: 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 Nobile  …see more

from £131 / night

£522 - £774 / week

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from £131 / night

1 / 14

Province of Siena / Montepulciano

1 3 3 nights min stay

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

from £66 / night

£435 / week

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from £66 / night

1 / 55

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £70 / night

£740 - £1000 / week

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from £70 / night

1 / 6

Province of Siena / Montepulciano

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Ask about pets; Private garden;
 …see more

from £74 / night

£435 / week

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from £74 / night

1 / 15

35827-Apartment Montepulciano - Abbadia di Montepulciano apartment sleeps 4

Montepulciano / Abbadia di Montepulciano

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car not necessary;
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.C.G.) wine are made.  …see more

from £102 / night

£710 - £1050 / week

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from £102 / night

1 / 12

Montepulciano / Abbadia di Montepulciano

3 7 1 night min stay

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Child friendly ; Car advised; Pet friendly;
 …see more

from £53 / night

£261 / week

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from £53 / night

(11) Excellent 

1 / 21

charming cottage in peaceful country setting

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 90 km; 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 £70 / night

£400 - £1792 / week

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from £70 / night

(2) Excellent 

1 / 17

VILLA BIANCA - Montepulciano farmhouse sleeps 4

Province of Siena / Montepulciano

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 106 km; Child friendly ; Car not necessary;
The apartment has two bedrooms one big bathroom and a service bath.The private entrance leads into a spacious lounge furnished with a authentic Tuscan table and chairs, a comfortable sofa set and coffee table and an open plan fire place very spacious and charming.The la  …see more

from £170 / night

£696 / week

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from £170 / night

(1) Excellent 

1 / 23

Tuscan Villa Argiano 1-2room ,Montepulciano, B&B

Province of Siena / Montepulciano

4 6 2 nights min stay

  • 4 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Ask owner if suitable for 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 floor of th  …see more

from £70 / night

£487 / week

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from £70 / night

1 / 22

Province of Siena / Montepulciano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 116 km; Child friendly ; Car advised;
 …see more

from £122 / night

£653 / week

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from £122 / night

1 / 18

The Artist's Villa (v042) - Gracciano villa sleeps 9

Montepulciano / Gracciano

4 9 7 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This unique villa has, on the ground floor, a large entrance hall, a large living room with kitchen, dining room and central fireplace, a double bedroom, a bedroom with french bed (which could sleep 2 people), a bathroom with a shower, a bathroom with bathtub. On the fi  …see more

from £210 / night

£1470 - £2400 / week

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from £210 / night

1 / 22

I CASALI DI TOSCANA - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Child friendly ; Car advised; Air conditioning;
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 £261 / night

£1827 / week

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from £261 / night

1 / 33

Country House Maramai in the lush Chiana valley

Montepulciano / Gracciano

5 9 7 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Maramai lies on the Gracciano estate, one of the most renowned producers of the Vino Nobile di Montepulciano, one hour south of Florence in the lush Chiana valley. The restored farmhouse with pool with 7 to 9 beds is the perfect base to explore the surrounding Tuscany l  …see more

from £295 / night

£2061 - £4105 / week

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from £295 / night

1 / 21

Villa Bacco with Pool (Max 16+4 ppl) - Valiano villa sleeps 20

Montepulciano / Valiano

8 20 7 nights min stay

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
Villa located on top of a hill and dipped between wineyards.Due to its strategic position, in Valiano di Montepulciano, half way from Rome to Florence and on the border between Tuscany and Umbria region, it will be easy to visit the most artistic towns in the heart of I  …see more

from £621 / night

£3914 / week

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from £621 / night

1 / 16

Luxury 4 bed house with views over Montepulciano

Province of Siena / Montepulciano

4 8 7 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Child friendly ; Car essential; No pets allowed;
This luxury 4 bedroom villa is furnished throughout to a high standard. The property sits in 4 acres of garden, surrounded by woods and vineyards. All the bedrooms have en-suite marble bathrooms and fantastic views of either Montepulciano or Montefollonico. Outside the  …see more

from £311 / night

£2174 - £3131 / week

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from £311 / night

1 / 5

Province of Siena / Montepulciano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Not suitable for children; No pets allowed; Private garden;
 …see more

from £87 / night

£414 / week

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from £87 / night

(7) Excellent 

1 / 26

Province of Siena / Montepulciano

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Car essential; Air conditioning;
 …see more

from £70 / night

£427 - £548 / week

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from £70 / night

1 / 11

Val di Chiana Farmhouse 627002 - Montepulciano farmhouse sleeps 18

Province of Siena / Montepulciano

9 18 4 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 4 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
Between the hills of Val di Chiana and the Val d'Orcia lying, while not far away from Umbria and Lake Trasimeno. It is a good starting point for trips to Montepulciano, Cortona, Montalcino, Chianciano (spa), Siena, Arezzo and Perugia. Montepulciano is not only famo  …see more

from £696 / night

£3566 / week

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from £696 / night

1 / 12

The Secret Garden Apartment Montepulciano

Province of Siena / Montepulciano

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Ask owner if suitable for children; No pets allowed; Private garden;
A rental apartment with a large garden in the centre of Montepulciano? It sounds impossible but it isn't! And Summer's Leases has found it!! So you can have a leisurely breakfast on the terrace, see some sights and have a nice lunch either at one of the many restaurants  …see more

from £71 / night

£496 - £705 / week

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from £71 / night

(2) Excellent 

1 / 25

Province of Siena / Montepulciano

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Air conditioning; Pet friendly;
 …see more

from £122 / night

£783 / week

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from £122 / night

1 / 6

Province of Siena / Montepulciano

4 10 1 night min stay

  • 4 bedrooms
  • Sleeps 10
  • 1 night min stay
Key info: Beach / lakeside relaxation; Not suitable for children; No pets allowed;
 …see more

from £148 / night

£870 / week

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from £148 / night

1 / 29

Province of Siena / Montepulciano

5 9 1 night min stay

  • 5 bedrooms
  • Sleeps 9
  • 1 night min stay
Key info: Swimming pool; Not suitable for children; Car advised;
 …see more

from £870 / night

£6087 / week

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from £870 / night

(1) Very Good 

1 / 22

Villa Poliziana San Benedetto - Montepulciano villa sleeps 7

Province of Siena / Montepulciano

3 7 1 night min stay

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Nearest beach 180 km; Child friendly ; Car advised;
La Villa è situata poco fuori le mura, in prossimità del Tempio di San Biagio. Internamente si trovano due camere da letto, due bagni, uno spazioso e luminoso salone con divano letto, cucina e sala da pranzo. Esternamente gode di un meraviglioso panorama che da' sull  …see more

from £87 / night

£522 / week

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from £87 / night

(1) Excellent 

1 / 63

Villa Bossona - Montepulciano villa sleeps 16

Province of Siena / Montepulciano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
Key info: Nearest beach 115 km; Swimming pool; Child friendly ;
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town. A small church with an enchanting bell tower is preserved in its original for  …see more

from £522 / night

£3392 - £3740 / week

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from £522 / night

(1) Excellent 

1 / 18

Province of Siena / Montepulciano

2 7 1 night min stay

  • 2 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £57 / night

£366 - £518 / week

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from £57 / night

1 / 83

il Molinaccio Montepulciano 3 - Montepulciano farmhouse sleeps 6

Province of Siena / Montepulciano

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car essential;
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  …see more

from £261 / night

£1522 / week

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from £261 / night

1 / 7

Il Casalone Apartment Oliveto - Montepulciano farmhouse sleeps 4

Province of Siena / Montepulciano

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
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 £53 / night

£235 - £427 / week

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from £53 / night

1 / 20

Montepulciano - 62889001 - Montepulciano farmhouse sleeps 6

Province of Siena / Montepulciano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
This beautiful independent villa in Tuscany has a private swimming pool and rests just 2km from the historical centre of charming Montepulciano. The property is well looked after and ideally positioned for visiting the beautiful Val d’Orcia area (Pienza, San Quirico d  …see more

from £150 / night

£879 - £1800 / week

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from £150 / night

1 / 34

Podere Sant' Albino - Sant'Albino villa sleeps 14

Montepulciano / Sant'Albino

7 14 7 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Nearest beach 115 km; 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 £373 / night

£2609 - £5392 / week

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from £373 / night

1 / 29

Montepulciano / Abbadia di Montepulciano

5 10 1 night min stay

  • 5 bedrooms
  • Sleeps 10
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £746 / night

£5218 / week

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from £746 / night

1 / 18

Febo Holiday - Montepulciano villa sleeps 4

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Ask about pets; Private garden;
Suite Home has two bedrooms one big bathroom and a service bath. The private entrance leads into a spacious lounge furnished with a authentic Tuscan table and chairs, a comfortable sofa set and coffee table and an open plan fire place very spacious and charming. The l  …see more

from £114 / night

£609 - £696 / week

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from £114 / night

1 / 7

Il Casalone Apartment Tre Laghi - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Not suitable for children; No pets allowed; 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 £53 / night

£235 - £427 / week

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from £53 / night

1 / 45

Province of Siena / Montepulciano

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
 …see more

from £627 / night

£2392 / week

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from £627 / night

1 / 8

Il Casalone Apartment Amiata - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Not suitable for children; No pets allowed; 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 £96 / night

£366 - £609 / week

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from £96 / night

(7) Excellent 

1 / 41

Unique, charming farmhouse in Tuscany countryside with shared outdoor pool, sleeps up to 6

Province of Siena / Montepulciano

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 0 km; 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 £72 / night

£500 - £890 / week

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from £72 / night

1 / 9

Province of Siena / Montepulciano

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car not necessary;
 …see more

from £87 / night

£479 - £627 / week

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from £87 / night

(41) Excellent 

1 / 21

La Casina Toscana, central with parking and wi-fi

Province of Siena / Montepulciano

3 5 3 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 158 km; Child friendly ; Car advised;
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 £61 / night

£348 - £609 / week

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from £61 / night

1 / 24

Villa in Tuscany - Montepulciano villa sleeps 12

Province of Siena / Montepulciano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
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 £218 / night

£2131 - £3653 / week

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from £218 / night

Top Destination reviews

The Beautiful Sun Apartment
Well maintained apartment and very helpful owner

Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and everything we needed was there. All to a good s … see more
La Casina Toscana, central with parking and wi-fi
Clean, comfortable and cozy house with privacy and convenience to Montepuciano

We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close enough to walk to the Montepulciano town. The place was very clean and thoughtf … see more

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