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49 Holiday homes

Filters applied: City breaks (49)

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

(5) Excellent 

1 / 52

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Great for children of all ages ; Car not necessary; Some pets are welcome - please contact the owner;
 …see more

from £118 / night

£673 - £757 / week

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from £118 / night

(41) Excellent 

1 / 21

La Casina Toscana, central with parking and wi-fi

Tuscany / Province of Siena / Montepulciano

3 bedroomsSleeps 53 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 158 km; Great for children of all ages ; 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 £59 / night

£334 - £584 / week

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from £59 / night

(18) Excellent 

1 / 24

The Beautiful Sun Apartment - Montepulciano apartment sleeps 6

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 61 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Nearest beach 170 km; Great for children of all ages ; 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 £100 / night

£583 - £1016 / week

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from £100 / night

(3) Excellent 

1 / 35

The Notary's House - Montepulciano apartment sleeps 6

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
Small charming flat, old residence of householder's great-grandfather, Notary in Montepulciano. Recently wholly restructured, very quiet, in a very beautiful position: in the centre of town, but facing the walls of the city, in a dominant position.Two nice bedrooms, sma  …see more

from £59 / night

£334 - £500 / week

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from £59 / night

(25) Excellent 

1 / 103

Tuscany / Province of Siena / Montepulciano

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 15 km; Swimming pool;
 …see more

from £421 / night

£2017 - £3992 / week

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from £421 / night

1 / 38

Tuscany / Province of Siena / Montepulciano

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed; Private garden;
 …see more

from £163 / night

£1137 - £1561 / week

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from £163 / night

(6) Excellent 

1 / 33

Lovely 2 bedroom holiday apartment in Tuscany

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
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 £63 / night

£0 / week

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from £63 / night

(7) Excellent 

1 / 41

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

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
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 / 27

Agriturismo Ardene - Montepulciano villa sleeps 14

Tuscany / Province of Siena / Montepulciano

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 100 km; Swimming pool;
Villa Ardene provides its guests with high level services in a magical, peaceful and unforgettable atmosphere. All the suites and apartments are equipped with whirlpool bath, air conditioning, satellite TV, internet connection.The interior space in “arte povera” has  …see more

from £565 / night

£3956 - £6060 / week

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from £565 / night

(6) Very Good 

1 / 45

Tuscany / Province of Siena / Montepulciano

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
 …see more

from £67 / night

£442 - £500 / week

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from £67 / night

(1) Excellent 

1 / 29

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Great for children of all ages ; Car essential;
 …see more

from £98 / night

£613 - £776 / week

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from £98 / night

(7) Excellent 

1 / 26

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Great for children of all ages ; Car essential; Air conditioning;
 …see more

from £68 / night

£412 - £530 / week

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from £68 / night

1 / 11

Holiday Home Casa Ciliano - Montepulciano apartment sleeps 5

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Pets welcome;
Casa Ciliano is an holiday house in Montepulciano, 60 Km far from Siena, it is inside the medieval wall, nearby Porta al Prato, that is the main gate to the historical centre with its Renaissance monuments. 50M far from Casa Ciliano you can see the Etruscan inscriptions  …see more

from £68 / night

£437 - £547 / week

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from £68 / night

(3) Very Good 

1 / 24

Great place for a Tuscan family holiday, 2 bedroom countryside apartments with shared pool

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
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 £67 / night

£0 / week

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from £67 / night

(1) Excellent 

1 / 29

Tuscany / Province of Siena / Montepulciano

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Great for children of all ages ; Air conditioning; Pets welcome;
 …see more

from £225 / night

£1167 - £1959 / week

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from £225 / night

(3) Good 

1 / 5

Tuscany / Province of Siena / Montepulciano

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Pets welcome;
 …see more

from £50 / night

£250 / week

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from £50 / night

(7) Excellent 

1 / 6

Tuscany / Province of Siena / Montepulciano / Valiano

1 bedroomSleeps 24 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Not suitable for children; Car essential;
 …see more

from £43 / night

£295 / week

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from £43 / night

(5) Excellent 

1 / 24

Tuscany / Province of Siena / Montepulciano

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Great for children of all ages ; Car advised; No pets allowed;
 …see more

from £65 / night

£384 / week

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from £65 / night

(9) Excellent 

1 / 25

The Little Arch of Memory - Montepulciano apartment sleeps 2

Tuscany / Province of Siena / Montepulciano

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Great for children of all ages ; No pets allowed;
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 £75 / night

£391 - £441 / week

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from £75 / night

1 / 22

Tuscany / Province of Siena / Montepulciano

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 116 km; Great for children of all ages ; Car advised;
 …see more

from £118 / night

£631 / week

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from £118 / night

1 / 83

il Molinaccio Montepulciano 3 - Montepulciano farmhouse sleeps 6

Tuscany / Province of Siena / Montepulciano

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; 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 £250 / night

£1459 / week

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from £250 / night

(15) Very Good 

1 / 97

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

Tuscany / Province of Siena / Montepulciano

7 bedroomsSleeps 161 night min stay

  • 7 bedrooms
  • Sleeps 16
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; 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 £500 / night

£2917 / week

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from £500 / night

(1) Very Good 

1 / 49

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
 …see more

from £125 / night

£584 / week

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from £125 / night

(2) Excellent 

1 / 25

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Great for children of all ages ; Air conditioning; Pets welcome;
 …see more

from £118 / night

£757 / week

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from £118 / night

(1) Excellent 

1 / 23

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

Tuscany / Province of Siena / Montepulciano

4 bedroomsSleeps 62 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 £67 / night

£0 / week

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from £67 / night

(5) Excellent 

1 / 22

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Great for children of all ages ; Car advised; No pets allowed;
 …see more

from £76 / night

£446 / week

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from £76 / night

1 / 11

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
 …see more

from £30 / night

£0 / week

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from £30 / night

1 / 37

AIA - 60 sq mt - La casa delle Querce - Acquaviva di Montepulciano farmhouse sleeps 5

Tuscany / Province of Siena / Montepulciano / Acquaviva di Montepulciano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
L'AIA it's a homy apartment of 60 sq mt. Climbing few doorsteps you enter the living-dining room embellished by brick walls,wooden beamed ceilings and local terracotta tiled floors. In the living-dining room there is a dining table, a sofa, some rustic Tuscan furniture,  …see more

from £84 / night

£500 - £892 / week

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from £84 / night

1 / 13

Casa al bosco - Montepulciano apartment sleeps 4

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
“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  …see more

from £92 / night

£642 - £817 / week

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from £92 / night

(1) Excellent 

1 / 36

POLICIANO Suite, 90 sq mt - La Casa delle Querce

Tuscany / Province of Siena / Montepulciano / Acquaviva di Montepulciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
The POLICIANO Suite is the largest apartment of La Casa delle Querce with its 90 sq meters. It comprises of a very spacious living dining-room, an ample cooking area, two bedrooms and two bathrooms each with shower. In the bedrooms there is air conditioning. One bedroom  …see more

from £117 / night

£700 - £1125 / week

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from £117 / night

(1) Excellent 

1 / 17

Tuscany / Province of Siena / Montepulciano

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; Some pets are welcome - please contact the owner;
 …see more

from £125 / night

£1000 - £1250 / week

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from £125 / night

(1) Excellent 

1 / 14

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Great for children of all ages ; Car essential; Some pets are welcome - please contact the owner;
 …see more

from £84 / night

£584 / week

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from £84 / night

(5) Very Good 

1 / 23

Tuscany / Province of Siena / Montepulciano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Great for children of all ages ; Some pets are welcome - please contact the owner; Private garden;
 …see more

from £71 / night

£459 - £550 / week

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from £71 / night

1 / 45

Tuscany / Province of Siena / Montepulciano

4 bedroomsSleeps 12Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Great for children of all ages ;
 …see more

from £600 / night

£2292 / week

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from £600 / night

1 / 14

Tuscany / Province of Siena / Montepulciano

4 bedroomsSleeps 93 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min stay
Key info: Not suitable for children; No pets allowed;
 …see more

from £750 / night

£3834 / week

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from £750 / night

1 / 19

Beautiful Tuscany villa near Montepulciano

Tuscany / Province of Siena / Montepulciano

5 bedroomsSleeps 101 night min stay

  • 5 bedrooms
  • Sleeps 10
  • 1 night min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
Ancient Borgo, consisting of several parts, a structure with 10 +2 beds, Eventually extra structure B 6 +2 Structure A is composed of the first floor, 5 bedrooms, of which two for disabled guests, each with private bathroom and air conditioning. on the ground floor a l  …see more

from £159 / night

£2084 / week

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from £159 / night

(1) Excellent 

1 / 19

Tuscany / Province of Siena / Montepulciano

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £75 / night

£450 - £700 / week

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from £75 / night

1 / 5

ARDENEX2 - Montepulciano farmhouse sleeps 2

Tuscany / Province of Siena / Montepulciano

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Ardene is located in Montepulciano and due to its unexpected, innovative and welcoming accommodation facilities it is one of the most exclusive farmhouse of this area. It is a country house in ancient stone and its origins date back to the medieval times. Ardene is the  …see more

from £100 / night

£0 / week

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from £100 / night

1 / 15

Tuscany / Province of Siena / Montepulciano

3 bedroomsSleeps 93 nights min stay

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min stay
Key info: Great for children of all ages ; Some pets are welcome - please contact the owner;
 …see more

from £146 / night

£917 / week

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from £146 / night

(8) Very Good 

1 / 11

Belguardo - Montepulciano apartment sleeps 6

Tuscany / Province of Siena / Montepulciano

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
The large apartment (116 sqm) is situated in the historical centre of Montepulciano. It is situated on the first floor of a historical building whose entrance opens onto the main street, a few steps from the most important archway (Porta al Prato) leading to the art tow  …see more

from £59 / night

£392 - £1045 / week

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from £59 / night

Top Destination reviews

The Grifo Apartment
Perfect!!

The apartment is spacious and clean. It's inside the historical center and it's perfect to visit it. We had a quiet stay . … 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
CasaMontepulciano Into the sunset
Into the bliss!

The moment we arrived at the Autostazione di Montepulciano, Luca greeted us with a big smile and and an open heart that made this trip so particularly memorable. His flat on up on the edge of the hill was as described and better. It comfortably held … see more
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

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