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148 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.

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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

(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 £518 / night

£3018 / week

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from £518 / night

1 / 4

Montepulciano / Gracciano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 200 km; Child friendly ; Car essential;
 …see more

from £44 / night

£302 / week

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from £44 / night

(5) Excellent 

1 / 24

Province of Siena / Montepulciano

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Child friendly ; Car advised; No pets allowed;
 …see more

from £67 / night

£394 / week

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from £67 / night

1 / 23

Province of Siena / Montepulciano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Child friendly ; Ask about pets;
 …see more

from £65 / night

£453 / week

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from £65 / 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 £616 / night

£3880 / week

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from £616 / night

1 / 9

apartment in Montefollonico - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Child friendly ; Ask about pets;
Villa Chiara is a self-catering accommodation located in Montefollonico. Free WiFi access is available. The apartment will provide you with a TV and a seating area. Complete with a refrigerator, the dining area also has kitchenware and a coffee machine. Featuring a show  …see more

Pricing unknown

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Pricing unknown

1 / 21

Lovely room in farmhouse in Montepulciano

Montepulciano / Acquaviva di Montepulciano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
Tenuta di Argiano a Montepulciano, located near MONTEPULCIANO, is surrounded by vineyards growing grapes for the famous local wines, Vino Nobile di Montepulciano and Rosso di Montepulciano, and is peaceful and quite. swimming pool and wifi . La Giara (35 m2) studio  …see more

from £61 / night

£423 / week

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from £61 / night

1 / 11

Province of Siena / Montepulciano

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Car advised; Ask about pets;
 …see more

from £31 / night

£212 / week

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from £31 / night

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Vino Nobile - Giardino - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Child friendly ;
Located amidst the enchanting garden of the property, this independent cottage in Montepulciano affords a dining area and a living room with fireplace and double sofa bed, a kitchen with its own breakfast area, and a double bedroom with its en-suite bathroom equipped wi  …see more

from £103 / night

£642 - £838 / week

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from £103 / night

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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 £209 / night

£1457 - £2380 / week

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from £209 / night

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Vino Nobile - Vigna - Montepulciano apartment sleeps 3

Province of Siena / Montepulciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Child friendly ;
This charming cottage in Montepulciano affords a dining area and a living room with fireplace and single sofa bed, a kitchenette and a double/twin bedroom. The cottage also has its own private bathroom with shower.Outside, it features its own private terrace. The cottag  …see more

from £103 / night

£599 - £795 / week

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from £103 / night

1 / 100

Vino Nobile - Fontana - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Child friendly ;
This enchanting suite in Montepulciano affords a dining-com-living area and a kitchen corner. The bedroom has a comfortable double bed and it affords an en-suite bathroom with whirlpool shower. The design of this suite is very peculiar, since the furniture has been crea  …see more

from £86 / night

£599 - £727 / week

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from £86 / night

(5) Excellent 

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Montorio - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; No pets allowed;
Montorio was built in 1300 as a convent and is located in the beautiful sopt in MOntepulciano , on the top of a private hill overlooking the church of San Biagio and the rolling hill. It is in a walking distance to the center of the town but ensure the privacy of a coun  …see more

from £113 / night

£776 / week

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from £113 / night

(2) Excellent 

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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 £169 / night

£690 / week

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from £169 / night

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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 £739 / night

£5173 / week

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from £739 / night

(3) Excellent 

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The Notary's House - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Child friendly ; 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 £61 / night

£345 - £518 / week

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from £61 / night

1 / 13

Province of Siena / Montepulciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 150 km; Swimming pool; Suitable for children age 5+;
 …see more

from £61 / night

£432 / week

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from £61 / night

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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 £121 / night

£647 / week

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from £121 / night

1 / 11

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Child friendly ; No pets allowed;
 …see more

Pricing unknown

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Pricing unknown

(7) Excellent 

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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 £69 / night

£423 - £544 / week

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from £69 / night

(11) Excellent 

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CasaMontepulciano Into the sunset - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: 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 £99 / night

£599 - £742 / week

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from £99 / night

1 / 18

Province of Siena / Montepulciano

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Child friendly ; Pet friendly;
 …see more

from £69 / night

£483 / week

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from £69 / 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

£492 - £699 / week

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from £71 / night

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I Tigli - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 115 km; Swimming pool; Child friendly ;
I Tigli is a splendid apartment with two bedrooms and two bathrooms which is part of a property with a total of 6 apartments sharing a pool. Located in the magnificent atmosphere of the hills surrounding the ancient town of Montepulciano, famous for its history, art, ar  …see more

from £100 / night

£647 - £854 / week

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from £100 / 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

(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

£475 - £569 / week

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from £74 / 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 £292 / night

£2044 - £4069 / week

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from £292 / night

(1) Very Good 

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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

£518 / week

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from £87 / 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 £259 / night

£1509 / week

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from £259 / night

(3) Very Good 

1 / 24

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

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; 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 £69 / night

£483 / week

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from £69 / night

1 / 11

Province of Siena / Montepulciano

1 2 2 nights min stay

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

from £61 / night

£380 / week

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from £61 / night

(11) Excellent 

1 / 33

Pretty 2 bedroom holiday apartment in the heart of

Province of Siena / Montepulciano

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: 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 £65 / night

£345 - £571 / week

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from £65 / 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 £121 / night

£776 / week

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from £121 / night

1 / 6

Province of Siena / Montepulciano

2 4 3 nights min stay

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

from £108 / night

£863 / week

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from £108 / night

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Il Molinaccio di Montepulciano 1 - Montepulciano farmhouse sleeps 2

Province of Siena / Montepulciano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 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 £95 / night

£518 / week

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from £95 / 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;
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from £56 / night

£359 - £509 / week

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from £56 / night

(18) Excellent 

1 / 24

The Beautiful Sun Apartment - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Nearest beach 170 km; 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 £103 / night

£603 - £1051 / week

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from £103 / 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

£475 - £621 / week

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from £87 / night

(4) Very Good 

1 / 19

Province of Siena / Montepulciano

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £95 / night

£518 / week

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from £95 / 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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