Walking holiday villas and apartments Montepulciano | Holiday Lettings

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75 Holiday homes

Filters applied: Walking holidays (75)

(11) Excellent 

21

charming cottage in peaceful country setting - Gracciano cottage sleeps 6

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

£383 - £1792 / week

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from £70 / night

(7) Excellent 

33

Lovely 2 bedroom holiday apartment in Tuscany - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
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 £61 / night

£461 - £592 / week

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from £61 / night

(18) Excellent 

24

The Beautiful Sun Apartment - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • 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 £104 / night

£608 - £1060 / week

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from £104 / night

(3) Excellent 

35

The Notary's House - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

£348 - £522 / week

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from £61 / night

(42) Excellent 

21

La Casina Toscana, central with parking and wi-fi - Montepulciano cottage sleeps 5

Province of Siena / Montepulciano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 158 km
  • Child friendly
  • Air conditioning
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

(8) Excellent 

41

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

Province of Siena / Montepulciano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 - £775 / week

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from £72 / night

(8) Excellent 

26

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from £70 / night

£427 - £548 / week

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from £70 / night

(7) Very Good 

52

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

 …see more

from £140 / night

£740 - £783 / week

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from £140 / night

(1) Excellent 

23

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

Province of Siena / Montepulciano

4 2 2 nights min

  • 4 bedrooms
  • Sleeps 2
  • 2 nights min
  • 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 £61 / night

£427 / week

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from £61 / night

(5) Excellent 

24

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly

 …see more

from £68 / night

£400 / week

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from £68 / night

11

Holiday Home Casa Ciliano - Montepulciano apartment sleeps 5

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Pet friendly
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 £70 / night

£453 - £566 / week

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from £70 / night

18

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

Montepulciano / Gracciano

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
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 - £1766 / week

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from £210 / night

40

Il Molinaccio di Montepulciano 1 - Montepulciano farmhouse sleeps 2

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
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 £96 / night

£522 / week

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from £96 / night

(9) Very Good 

6

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Pet friendly

 …see more

from £44 / night

£305 / week

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from £44 / night

(6) Very Good 

45

Province of Siena / Montepulciano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £74 / night

£479 - £522 / week

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from £74 / night

83

il Molinaccio Montepulciano 3 - Montepulciano farmhouse sleeps 6

Province of Siena / Montepulciano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
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

29

Montepulciano / Abbadia di Montepulciano

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £739 / night

£5173 / week

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from £739 / night

24

Villa in Tuscany - Montepulciano villa sleeps 12

Province of Siena / Montepulciano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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 / week

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from £218 / night

(9) Excellent 

25

The Little Arch of Memory - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
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 £77 / night

£362 - £457 / week

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from £77 / night

(4) Very Good 

24

Great place for a Tuscan family holiday, 2 bedroom countryside apartments with shared pool - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • 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 £61 / night

£427 / week

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from £61 / night

(4) Very Good 

19

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly

 …see more

from £95 / night

£518 / week

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from £95 / night

(3) Very Good 

24

Pietra del Diavolo - Montepulciano farmhouse sleeps 10

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
Villa Pietra del Diavolo, recently restored, is situated in one of the most beautiful and panoramic hill around Montepulciano.“Pietra del Diavolo” is named after a stone composed of tufa layers particularly common in the local area.The property is situated in the he  …see more

from £237 / night

£1653 - £2000 / week

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from £237 / night

(2) Excellent 

25

Province of Siena / Montepulciano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £122 / night

£783 / week

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from £122 / night

(6) Excellent 

22

Province of Siena / Montepulciano

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly

 …see more

from £79 / night

£461 / week

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from £79 / night

(1) Very Good 

22

Villa Poliziana San Benedetto - Montepulciano villa sleeps 7

Province of Siena / Montepulciano

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 180 km
  • Child friendly
  • Pet friendly
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

(3) Good 

5

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Pet friendly

 …see more

from £53 / night

£261 / week

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from £53 / night

5

ARDENEX2 - Montepulciano farmhouse sleeps 2

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 £105 / night

£731 / week

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from £105 / night

6

Province of Siena / Montepulciano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £74 / night

£435 / week

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from £74 / night

43

Province of Siena / Montepulciano

3 9 3 nights min

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min
  • Child friendly
  • Ask about pets

 …see more

from £153 / night

£957 / week

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from £153 / night

26

Villa Croce - Sant'Albino villa sleeps 10

Montepulciano / Sant'Albino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano. The property is situated in the heart a working farm with breathtaking views over the valley where Vino Nobile di Montepulciano is produced. The villa ha  …see more

from £237 / night

£1653 - £3131 / week

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from £237 / night

(1) Very Good 

49

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £130 / night

£604 / week

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from £130 / night

34

Podere Sant' Albino - Sant'Albino villa sleeps 14

Montepulciano / Sant'Albino

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • 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

23

I Tigli - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

£653 - £861 / week

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from £100 / night

11

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £31 / night

£212 / week

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from £31 / night

31

Il Poggiarone Montepulciano - Montepulciano villa sleeps 14

Province of Siena / Montepulciano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Private garden
Il Poggiarone is a splendid farmhouse with typical Tuscan architectural features, set in an extremely panoramic position and the ideal destination for those who are looking for a holiday which is a mix of art, history and nature. The beautiful villa is near the owner's  …see more

from £163 / night

£1138 - £2104 / week

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from £163 / night

(1) Excellent 

13

B&B Casale a Poggiano-The best Breakfast and more - Montepulciano b&b sleeps 2

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly
The comfortable room has a private bathroom and face on the beautiful garden Our Bed and Breakfast is in a particular area of Tuscany (Italy), in Siena district and combines the quiet of the country with the closeness of interesting Interesting Places as Florence, Ro  …see more

from £74 / night

£435 / week

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from £74 / night

33

Country House Maramai in the lush Chiana valley - Gracciano villa sleeps 9

Montepulciano / Gracciano

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
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 - £3470 / week

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from £295 / night

(15) Very Good 

97

7 bedroom Tuscan farmhouse near rennaissance town of Montepulciano, features include jacuzzi, private garden and pool - Montepulciano farmhouse sleeps 16

Province of Siena / Montepulciano

7 16 1 night min

  • 7 bedrooms
  • Sleeps 16
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
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

(5) Excellent 

20

Montorio - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
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 £114 / night

£783 / week

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from £114 / night

(2) Excellent 

17

VILLA BIANCA - Montepulciano farmhouse sleeps 4

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • 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

Top Destination reviews

Luxury 4 bed house with views over Montepulciano
Amazing Location and Hospitality

We enjoyed a very relaxing week at La Casina with two other couples in July 2016. The villa is very spacious, well appointed and comfortable, and the kitchen is well equipped. La Casina has a commanding view of the surrounding vineyards and olive g … 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
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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