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124 Results   |  

Excellent 5/5 

22 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

3 Nights min stay

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from £51 / night

£355 - £440 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
Brand new apartment, functional, quiet, well furnished, with parking and garden, free wifi, close to the owners, close to the supermarket and at a great wine restaurant near Montepulciano, Pienza, Siena, Val d'Orcia, Cortona, Arezzo , Perugia, Assisi. Car recommended. T  …see more

Excellent 5/5 

19 Photos

Montepulciano / Gracciano

Apartment / 2 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

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from £61 / night

£426 - £852 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Agriturismi nel sud della Toscana , a Montepulciano , tra la Val d'Orcia e la Valdichiana , a conduzione familiare , di piccole dimensioni ,vicino al centro storico, con vista panoramica , coltivazioni biologiche di uva , olivi , alberi da frutta IL Sorbo è assolutam  …see more

Excellent 5/5 

11 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

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from £41 / night

£284 - £497 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
A romantic, panoramic location in the heart of Montepulciano, for a delightful holiday in an ancient home in the historical centre in one of the most beautiful towns of Tuscany! Charming House in Montepulciano!  …see more

Featured properties

Excellent 5/5 

24 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 4

Excellent 5/5 

3 Nights min stay

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from £47 / night

£327 - £355 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
Brand new apartment, functional, quiet, well furnished, with parking and garden, free wifi, close to the owners, close to the supermarket and at a great wine restaurant near Montepulciano, Pienza, Siena, Val d'Orcia, Cortona, Arezzo , Perugia, Assisi. Car recommended. T  …see more

Very Good 4.5/5 

98 Photos

Province of Siena / Montepulciano

Farmhouse / 7 Bedrooms / sleeps 16

Very Good 4.5/5 

1 night min stay

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from £355 / night

£2483 - £2837 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Swimming pool 15x5mt, cleaned using salt not chlorine. 3D archery range with wild animal targets, bow rental and trainer available. Try Alessandro's traditional cousine, it will surprise you! Our cellar and vineyards are open for visit, taste our Rosso di Montepulciano  …see more

Excellent 5/5 

45 Photos

Province of Siena / Montepulciano

House / 3 Bedrooms / sleeps 5

Excellent 5/5 

2 Nights min stay

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from £51 / night

£355 - £426 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Casa 5 posti letto a Montepulciano, ottima posizione panoramica sulla campagna. Circondata da uliveti. Vicinissima al Centro Storico di Montepulciano raggiungibile a piedi a circa 1 chilometro. Posto auto riservato. Caminetto, lavatrice, ampie terrazze. Riscaldamento.  …see more

Very Good 4.5/5 

52 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 5

Very Good 4.5/5 

2 Nights min stay

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from £66 / night

£461 - £532 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Ampio appartamento all'ultimo piano di palazzo d'epoca situato nel centro storico di Montepulciano. Recentemente ed elegantemente arredato con mobili d'antiquariato. Dotato di ogni comfort. 2 grandi camere,3 bagni, living, cucina attrezzata, wifi, tv digitale, ascensore  …see more

17 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 5

3 Nights min stay

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from £59 / night

£412 - £852 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful holiday resort near Montepulciano and Pienza  …see more

100 Photos

Province of Siena / Montepulciano

House / 1 Bedroom / sleeps 2

Short stays welcome

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from £55 / night

£381 - £587 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
2-room apartment 40 m2 on 2 levels, tasteful furnishings: living/dining room with 1 sofabed and kitchen corner. Exit to the garden. Upper floor: 1 double bedroom with panoramic window with satellite TV. Shower/bidet/WC. Heating (extra). Garden. Sitting area. Facilities:  …see more

43 Photos

Province of Siena / Montepulciano

Farmhouse / 1 Bedroom / sleeps 2

1 night min stay

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from £59 / night

£412 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
single room in a Villa with only 7 rooms. Infinity pool sanitized using salt and not chlorine, far better for your skin and eyes. We are a winery where you may visit our cellar and taste our wine,Il Golo,Rosso di Montepulciano DOC, Grappa, Finocchiaccio and marmelades.  …see more

25 Photos

Province of Siena / Montepulciano

House / 3 Bedrooms / sleeps 6

2 Nights min stay

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from £152 / night

£1064 - £1383 / week

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Key info:

  • Suitable for children over 5
  • Car advised
  • No pets allowed
CAMERE 3 POSTI LETTO 6 BAGNI 3 1/2 SAUNA CAMINO  …see more

17 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 2

4 Nights min stay

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from £38 / night

£263 - £568 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
holiday resort located in the middle of a vine yard, few minutes from Montepulciano. Excellent wine for tasting  …see more

100 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

Short stays welcome

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from £100 / night

£694 - £1035 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
3-room apartment 111 m2 on 1st floor. Spacious and bright, very beautiful and tasteful furnishings: living room with satellite TV. 1 double bedroom with bathroom, double hand-basin, whirlpool and satellite TV. 1 double bedroom with bath/shower/bidet/WC. Kitchenette (2 c  …see more

24 Photos

Province of Siena / Montepulciano

House / 4 Bedrooms / sleeps 10

2 Nights min stay

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from £155 / night

£1082 - £2137 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome

4-room house 350 m2 on 2 levels, spacious and bright, renovated, antique and tasteful furnishings: large living room 60 m2, window onto the courtyard with open fireplace, dining table and TV (flat screen TV), stereo unit and DVD. Exit to the garden. 1 double bedroom  …see more

Excellent 5/5 

27 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

2 Nights min stay

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from £31 / night

£213 - £490 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
The flat ws restored in 2001, It's about 150 mt from Piazza Grande and 30 mt from the main street. At your arrival the owner will give a free pass to enter in restricted area and to park just in front of the flat for your stay Free parking available and restricted area  …see more

Excellent 5/5 

20 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

3 Nights min stay

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from £71 / night

£497 - £1064 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
At MOntorio is easy to arrive and difficult to live, will be your home in Tuscany. Montorio has a special and unique spot , and you will feel in love for it  …see more

17 Photos

Province of Siena / Montepulciano

Farmhouse / 4 Bedrooms / sleeps 8

2 Nights min stay

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from £142 / night

£993 - £1135 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Beautiful country house in Tuscany, Siena  …see more

4 Photos

Montepulciano / Gracciano

House / 4 Bedrooms / sleeps 6

2 Nights min stay

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from £36 / night

£249 / week

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Key info:

  • Nearest beach 200 km
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
Cas colonica immersa nella campagna toscana con possibilità di escursioni, itinerari turistici ed enogastronomici, soggiorni nelle terme vicine di Rapolano e Bagnovignoni. Escursioni e visite dei siti della Val D'orcia e dei siti Etruschi di Chiusi.  …see more

24 Photos

Province of Siena / Montepulciano

Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

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from £1479 / night

£10348 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
This large farmhouse was famous as far back as the 10th century as a post-house for changing coaches and horses along the Via Francigena and the architecture of the house shows this origin.  …see more

20 Photos

Province of Siena / Montepulciano

Villa / 12 Bedrooms / sleeps 24

7 Nights min stay

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from £1915 / night

£13405 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
The villa is elegant and majestic in its eighteenth century form, the location is stunning with excellent furnishing and a beautiful garden, a welcoming and cozy atmosphere in a perfect Italian style Villa.  …see more

Excellent 5/5 

22 Photos

Montepulciano / Gracciano

Cottage / 2 Bedrooms / sleeps 6

Excellent 5/5 

3 Nights min stay

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from £40 / night

£277 - £688 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
This charming rural cottage is a converted farm building in the heart of the countryside near Montepulciano. It is ideally situated with its own private garden space surrounded by hills and vineyards, where guests can relax and enjoy the peaceful surroundings. It is  …see more

Excellent 5/5 

6 Photos

Montepulciano / Valiano

House / 1 Bedroom / sleeps 2

Excellent 5/5 

3 Nights min stay

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from £31 / night

£213 - £284 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car essential
  • Air conditioning
  • Pets welcome
Il Grottino è un delizioso terratetto, ristrutturato nel tipico stile toscano. Situato nel centro storico della piccola e tranquilla Valiano (Montepulciano), si tratta di un luogo strategico a pochi chilometri dalle principali mete turistiche di Toscana e Umbria.  …see more

Excellent 5/5 

24 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

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from £61 / night

£425 - £1028 / week

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Key info:

  • Nearest beach 170 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Shining, fresh, large and modern 2 bedroom apartment . You can easily access to the historic part of Montepulciano and its old style and art shops, monuments and churches (100mt.). Also very close to all of the others Montepulciano 's facilities. In the core of Tuscany  …see more

23 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 4

1 night min stay

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from £56 / night

£391 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
montepulciano casa vacanze giardino relax pienza A pochi kilometri si trova il centro Termale di Montepulciano, e le terme sensoriali di chianciano terme  …see more

Excellent 5/5 

21 Photos

Province of Siena / Montepulciano

Cottage / 3 Bedrooms / sleeps 5

Excellent 5/5 

3 Nights min stay

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from £51 / night

£355 - £497 / week

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Key info:

  • Nearest beach 158 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Independent villa with garden and exclusive parking. Immersed in the Tuscan countryside just 5 minutes walk from the center of Montepulciano, from the bus station and supermarket. Air-conditioned rooms with free use of wi-fi. Close to Val D'Orcia Cortona Pienza Siena.  …see more

6 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

1 night min stay

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from £51 / night

£355 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Struttura situata a 2 km dal centro storico di Montepulciano, situata su una collina con vista diretta sul paese e sulle vigne dalle quali viene prodotto il vino nobile di Montepulciano e sulla Valdichiana. Oltre al giardino interno recintato è presente anche un piccol  …see more

24 Photos

Province of Siena / Montepulciano

Villa / 6 Bedrooms / sleeps 12

4 Nights min stay

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from £249 / night

£1738 - £3171 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Nearby there are others agreeable towns like Pienza, Cortona, San Quirico d'Orcia, making it an ideal destination from which to savor the full essence of Tuscany. All around the villa an enchanting garden equipped with gazebo, table and chairs, the swimming pool  …see more

6 Photos

Province of Siena / Montepulciano

Guest house / 3 Bedrooms / sleeps 6

1 night min stay

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from £51 / night

£355 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Altes restauriertes Landhaus  …see more

9 Photos

Montepulciano / Abbadia di Montepulciano

Apartment / 1 Bedroom / sleeps 4

1 night min stay

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from £102 / night

£710 / week

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Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
Agriturismo natura terme ristorante montepulciano pienza famiglia cortona affitto vespe campagna relax vino enogastronomia zafferano prodotti tipici Marmellate confetture toscana outlet val di chiana val d'orcia lago  …see more

10 Photos

Montepulciano / Abbadia di Montepulciano

B&B / 1 Bedroom / sleeps 4

1 night min stay

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from £57 / night

£398 - £497 / week

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Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
Agriturismo natura terme ristorante montepulciano pienza famiglia cortona affitto vespe campagna relax vino enogastronomia zafferano prodotti tipici Marmellate confetture toscana outlet val di chiana val d'orcia lago  …see more

29 Photos

Province of Siena / Montepulciano

Villa / 4 Bedrooms / sleeps 9

1 night min stay

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from £568 / night

£3972 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Ad un solo chilometro dal centro di Montepulciano, su un colle circondato da ordinate vigne, vi attende questo bellissimo casale del '600 per offrirvi magiche e raffinate armosfere. Due magnifiche suites con idromassaggio e due eleganti stanze matrimoniali la suggestiva  …see more

15 Photos

Province of Siena / Montepulciano

B&B / 3 Bedrooms / sleeps 9

1 night min stay

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from £35 / night

£242 - £781 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
b&b nella campagna di Montepulciano, Punto strategico per visitare sia la Toscana che l'Umbria.  …see more

14 Photos

Province of Siena / Montepulciano

B&B / 4 Bedrooms / sleeps 9

3 Nights min stay

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from £467 / night

£3263 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Palazzo Nobile di San Donato is a luxury bed and breakfast and residenza d'epoca, period house set in an ancient medieval noble “tower house” in Montepulciano Historical centre, Tuscany can be rented for groups of 8/9  …see more

6 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £102 / night

£710 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Splendida ubicazione, vicinanza ai parcheggi, estremamente luminoso con affaccio sulla campagna. Silenziosissimo, pur essendo ubicato nel centro del paese le nuovissime finestre isonorizzate lo rendono estremamente silenzioso.  …see more

9 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 2

2 Nights min stay

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from £41 / night

£284 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
ersonal check in and check out, guests will have my mobile telephone number for any possible further assistance required. I can organize wine tours , tuscan cookery courses , horse riding. A full brochure describing all local activities is provided upon arrival . st  …see more

21 Photos

Montepulciano / Valiano

Villa / 8 Bedrooms / sleeps 20

Short stays welcome

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from £456 / night

£3192 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
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 Italy  …see more

20 Photos

Province of Siena / Montepulciano

Villa / 5 Bedrooms / sleeps 10

3 Nights min stay

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from £193 / night

£1346 - £2552 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Villa for rent situated inside a farm just outside the town of Montepulciano, in the hills south of Siena, Tuscany. Located on a hillside, the villa has a breathtaking view of the vineyards that produce Vino Nobile di Montepulciano, one of the wines that makes the Itali  …see more

34 Photos

Province of Siena / Montepulciano

Villa / 7 Bedrooms / sleeps 14

3 Nights min stay

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from £254 / night

£1773 - £4255 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Beautiful stone-built villa rental that has been completely renovated and transformed into a comfortable, exclusive holiday residence, situated near Montepulciano in the beautiful Tuscan countryside. This area of the countryside is, for the most part, made up of the vin  …see more

19 Photos

Province of Siena / Montepulciano

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £198 / night

£1383 - £3298 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Elegant air-conditioned villa with private pool to rent close to Montepulciano – sleeps 8 From 2300€ to 4650€ a week  …see more

13 Photos

Province of Siena / Montepulciano

Villa / 6 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £760 / night

£5320 - £6504 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
If your dream of a Tuscan vacation includes views of rolling green hills, rustic stone architecture and dining on local produce every day, villa Penelope is a dream come true. The renovated six-bedroom stone farmhouse, set on a hilltop just outside Montepulciano, has go  …see more

18 Photos

Province of Siena / Montepulciano

Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

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from £901 / night

£6307 - £8421 / week

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Key info:

  • Not suitable for children
  • No pets allowed
The splendid residence of Il Maniero sits majestically on top of a hill with commanding views over the typical Tuscan countryside, and Chiana Valley. Overlooking the historic town of Cetona, Il Maniero accommodates up to 14 people in great style and superlative comfort.  …see more

18 Photos

Montepulciano / Sant'Albino

Villa / 5 Bedrooms / sleeps 10

3 Nights min stay

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from £264 / night

£1842 - £2552 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
La Cantina Villa for rent with swimming pool in Montepulciano  …see more

34 Photos

Montepulciano / Sant'Albino

Villa / 7 Bedrooms / sleeps 14

3 Nights min stay

Add to shortlist

from £325 / night

£2269 - £4255 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Villa degli Olivi Villa for rent with swimming pool in Montepulciano  …see more

23 Photos

Montepulciano / Gracciano

Villa / 5 Bedrooms / sleeps 9

7 Nights min stay

Add to shortlist

from £241 / night

£1681 - £3288 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Maramai, now a charming country house, used to be a small farm with 3 separate buildings. It is named after the Tuscan farmer's family who lived there until the early '70s.  …see more

26 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £36 / night

£249 - £497 / week

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Key info:

  • Not suitable for children
  • Pets welcome
 …see more

100 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 5

Short stays welcome

Add to shortlist

from £54 / night

£376 - £897 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
3-room apartment 45 m2: living/dining room with 1 sofabed and TV. 1 double bedroom. 1 room with 2 beds. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Included: Power costs, Final cleaning, Laundry (initial supply of bed linen and towels), No Local Tax charged for c  …see more

100 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 4

Short stays welcome

Add to shortlist

from £46 / night

£318 - £855 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
2-room apartment 40 m2: living room with 1 double sofabed and TV. 1 double bedroom. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Included: Power costs, Final cleaning, Laundry (initial supply of bed linen and towels), No Local Tax charged for children Available on  …see more

100 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 2

Short stays welcome

Add to shortlist

from £37 / night

£259 - £690 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
1-room apartment 25 m2: living/dining room with 1 double bed and TV. Kitchenette. Shower/bidet/WC. 1 pet/ dog allowed. Included: Power costs, Final cleaning, Laundry (initial supply of bed linen and towels), No Local Tax charged for children Available on site with supp  …see more

100 Photos

Province of Siena / Montepulciano

House / 4 Bedrooms / sleeps 10

Short stays welcome

Add to shortlist

from £129 / night

£897 - £1604 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
4-room house 350 m2 on 2 levels, spacious and bright, renovated, antique and tasteful furnishings: large living room 60 m2, window onto the courtyard with open-hearth fireplace, dining table and TV (flat screen), hi-fi system and DVD. Exit to the garden. 1 double bedroo  …see more

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Province of Siena / Montepulciano

Apartment / 3 Bedrooms / sleeps 8

Short stays welcome

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from £84 / night

£587 - £718 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
5-room apartment "Lecci", for 8 people, 96 m2, on the upper floor, comfortable and rustic furnishings. Living/dining room with satellite-TV and open fireplace. Smoking allowed. Internet (Wireless LAN [WLAN]). 1 double sofa bed. Sleeping room with 1 double bed. Sleepin  …see more

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