Air conditioned apartments and villas to rent in Province of Siena

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981 Holiday homes

Filters applied: Air conditioning (981)

1 / 13

15656-Holiday house San Gimign - San Gimignano villa sleeps 4

Province of Siena / San Gimignano

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Two Bedroom Detached House San Gimignano<br><br>Il Vecchio Fienile is a beautiful detached house with private swimming pool, surrounded by its own well kept garden with wonderful views over vineyards and cypress groves towards medieval San Gimignano visible  …see more

from £122 / night

£849 - £1951 / week

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from £122 / night

1 / 101

Emma - Melograno - Bagno Vignoni apartment sleeps 4

Province of Siena / Bagno Vignoni

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
Melograno apartment on the ground floor of the main farmhouse is traditional in style with high, beamed ceilings and an original stone wall, adding lots of character. It can accommodate up to four, offering one double bedroom and a double sofa bed in the living room. Th  …see more

from £67 / night

£409 - £584 / week

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from £67 / night

(3) Excellent 

1 / 35

The Notary's House - Montepulciano apartment sleeps 6

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

1 / 55

Province of Siena / Cetona

2 bedroomsSleeps 43 nights min stay

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

from £100 / night

£542 - £625 / week

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from £100 / night

1 / 16

Gorgeous 2 bedroom villa in the Val d'Orcia region, features shared pool, private garden and barbecue

Montalcino / Val d'Orcia

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Located in the Val d'Orcia region south of Siena. This area has been declared a world heritage site by UNESCO. The house is located on a hill with panoramic views over the countryside and only 2 mins from the village of Montisi. Sitting out on your terrazza overloo  …see more

from £72 / night

£500 - £1080 / week

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from £72 / night

(7) Excellent 

1 / 6

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 £42 / night

£292 / week

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from £42 / night

(1) Excellent 

1 / 12

Rapolano Terme / Serre di Rapolano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 110 km; Great for children of all ages ; Car advised;
 …see more

from £50 / night

£292 - £567 / week

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from £50 / night

1 / 4

Il Forno - San Fabiano apartment sleeps 5

Monteroni d'Arbia / San Fabiano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
The villa Podernovo offers a nice apartment called Il Forno, with stunning view on the sunflowers fields, with all comforts such air conditioning.The apartment is at first floor of the villa, with a master bedroom with king size bed, a bathroom with shower and jacuzzi t  …see more

from £109 / night

£625 - £834 / week

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from £109 / night

1 / 100

Pericle - Province of Siena villa sleeps 10

Tuscany / Province of Siena

5 bedroomsSleeps 104 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
ExteriorsCrete Senesi is a wonderful region located in the south of Siena and it boasts fantastic and very unique landscape; rolling hills, winding roads, medieval hamlets and strong traditions characterize the region and give it a very particular enchantment.All the ci  …see more

from £250 / night

£1059 - £1334 / week

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from £250 / night

1 / 20

Rose Farm (v048) - Castiglione D'Orcia villa sleeps 21

Province of Siena / Castiglione D'Orcia

1 bedroomSleeps 217 nights min stay

  • 1 bedroom
  • Sleeps 21
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Large farmhouse divided into 4 apartments and 2 double bedrooms with bathrooms. Each apartment has a private entrance and two bedrooms (double, single or twin) each with bathrooms, kitchenette or kitchen. Laundry room. A large communal living room with fireplace is av  …see more

from £439 / night

£3067 - £4750 / week

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from £439 / night

1 / 7

Province of Siena / Casole d'Elsa

1 bedroomSleeps 4Min stay varies

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

from £71 / night

£459 - £784 / week

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from £71 / night

(7) Excellent 

1 / 26

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 £67 / night

£409 - £525 / week

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from £67 / night

1 / 99

Province of Siena / San Gimignano

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £101 / night

£631 - £832 / week

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from £101 / night

(4) Excellent 

1 / 21

La Chiesina - Casaglia villa sleeps 6

San Gimignano / Casaglia

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 75 km; Swimming pool; Great for children of all ages ;
The villa was an ancient historical structure going back to before the year 1200, originally the chapel "Santa Maria Church", near the burg of Casaglia. Over the centuries, the chapel was deconsecrated to become, first a watchtower, and then a place where the  …see more

from £125 / night

£834 - £1917 / week

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from £125 / night

(1) Excellent 

1 / 29

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

1 / 24

Casa Corte - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Suitable for children age 5+;
This beautiful and tastefully furnished 2 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the won  …see more

from £47 / night

£325 - £692 / week

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from £47 / night

1 / 35

Relais Montemaggiore- Camera - Bettolle b&b sleeps 3

1 bedroomSleeps 31 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Camera composta da una camera matrimoniale, un letto singolo e un ampio bagno con bagno turco privato. Situato a Bettolle, nella Regione Toscana, a 40 km da Siena, il Relais Montemaggiore è dotato di piscina all'aperto, vasca idromassaggio, attrezzature per barbecue, t  …see more

from £68 / night

£0 / week

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from £68 / night

(1) Good 

1 / 10

H 9 - Gaiole in Chianti apartment sleeps 5

Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 51 night min stay

  • 3 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. Details and the architecture are carefully planned.  …see more

from £84 / night

£375 / week

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from £84 / night

1 / 17

Galassia 22 - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 46 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. Details and the architecture are carefully planned.  …see more

from £109 / night

£659 / week

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from £109 / night

1 / 24

Pienza / Monticchiello

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Air conditioning; No pets allowed;
 …see more

from £61 / night

£325 / week

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from £61 / night

1 / 33

Appartamento Gaiole 40 - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Appartamento Gaiole 40 is a wonderful apartment in the heart of Chianti. This area is famous all over the world for its typical products and its superb wines. The apartment is located in Borgo di Gaiole, an ancient Borgo recently renovated that enjoys a magnificent view  …see more

from £89 / night

£619 - £945 / week

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from £89 / night

1 / 100

Petit Verdot - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
ExteriorsOriginally built in the 17th century rural Tuscany, the Villa has been restored without altering its original architecture. Siena's typical ocher colors dominate the villa's stone walls and diffuse a welcoming glow on the light blue of the infinity po  …see more

from £417 / night

£2917 - £3250 / week

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from £417 / night

(7) Excellent 

1 / 15

Holiday farmhouse apartment rental in Tuscany, property features beautiful garden and private fishing lake

Province of Siena / San Gimignano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 90 km; Swimming pool; Great for children of all ages ;
House with two apartments near San Gimignano in TuscanyHoliday Apartment offers 2 flats inside an old barn that were recently restructured.Both the apartments can accommodate up to 4 people and are composed of a bedroom with bathroom, a small bedroom and a dining room/k  …see more

from £59 / night

£400 - £559 / week

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from £59 / night

(1) Excellent 

1 / 29

I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi

Province of Siena / San Giovanni d'Asso

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Air conditioning;
I MELOGRANI II is a section of a villa settled in the heart of Siena countryside.This section (3 BDR APT) of the beautiful house,surrounded by a fenced olive grove with private pool (6x 5),lawn,stunning view on rolling Tuscan hills consists of a large entrance hall-sit  …see more

from £274 / night

£1916 - £2471 / week

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from £274 / night

1 / 22

Villa Gaiole - Siena villa sleeps 13

Province of Siena / Siena

5 bedroomsSleeps 132 nights min stay

  • 5 bedrooms
  • Sleeps 13
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Located between Florence and Siena in Chianti, Villa Gaiole's private hilltop position provides 360 degree panoramic views of the breathtaking Tuscan countryside. Set around an expansive central courtyard with barbeque area, this luxury villa rental provides visito  …see more

from £2474 / night

£8245 - £10994 / week

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from £2474 / night

(9) Excellent 

1 / 65

VILLA IRIS, LUXURY VILLA IN SAN GIMIGNANO

Province of Siena / San Gimignano

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 71 km; Swimming pool; Great for children of all ages ;
This superb villa, obtained from the careful restoration of an old brick kiln of 1737, is situated in a unique position on a hill opposite the towers of San Gimignano. The villa has been lovingly restored with materials of the highest quality and finished after long and  …see more

from £417 / night

£2917 - £6917 / week

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from £417 / night

(1) Excellent 

1 / 11

Siena apartments - Siena apartment sleeps 3

Province of Siena / Siena

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
Located on the hills of central Tuscany, at only 2 km from the walls of Siena, this charming holiday accommodation in Tuscany has been totally restored into 7 comfortable self-catering apartments with high quality furniture. All the holiday apartments have independent  …see more

from £59 / night

£367 - £459 / week

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from £59 / night

1 / 9

15655-Holiday house San Gimign - San Gimignano villa sleeps 4

Province of Siena / San Gimignano

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Two Bedroom Detached House San Gimignano<br><br>La Doccia is a lovely example of a restored Tuscan barn. It has its own swimming pool, garden terrace, and lovely views of the countryside, yet is only a short walk from the Porta San Matteo gateway into mediev  …see more

from £107 / night

£743 - £1718 / week

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from £107 / night

1 / 22

Casa Borgo - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 bedroomSleeps 47 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Great for children of all ages ;
This beautiful and tastefully furnished 1 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the won  …see more

from £43 / night

£300 - £575 / week

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from £43 / night

1 / 16

Maccalli - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Beautiful country house situated just a stone's throw away from San Gimignano, an attractive medieval town with a unique collection of towers and winding lanes set in the heart of the Tuscan countryside. This farmhouse enjoys spectacular views over a picturesque rural l  …see more

from £123 / night

£858 - £1255 / week

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from £123 / night

(1) Excellent 

1 / 100

Magda - San Gimignano villa sleeps 12

Province of Siena / San Gimignano

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 90 km; Swimming pool; Great for children of all ages ;
Exterior:Perched on top on a hill, in the heart of Chianti countryside, Villa Magda boasts what must be one of the most enviable views of Tuscany: rolling Chianti hills decked with vines and olives, crowned by the incredible profile of San Gimignano's towers (locat  …see more

from £709 / night

£4500 - £5417 / week

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from £709 / night

(6) Very Good 

1 / 24

Villa Caprera. Casa Borgianni - Caprera farmhouse sleeps 6

Siena / Caprera

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 100 km; Great for children of all ages ; Car advised;
A stylish apartment close to Siena ancient city walls, still surrounded by olive groves and fields; ideal for visitors looking for a quite lodge. The farmhouse is part of a unique Liberty village built by Garibaldi's doctor in 1880. Local shops are at walking dista  …see more

from £125 / night

£817 - £1042 / week

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from £125 / night

(1) Excellent 

1 / 20

Holiday Resort in Montepuciano B - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 bedroomSleeps 44 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearest village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists  …see more

from £57 / night

£400 - £788 / week

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from £57 / night

1 / 100

Castellina In Chianti 46441 - Castellina In Chianti villa sleeps 16

Province of Siena / Castellina In Chianti

8 bedroomsSleeps 167 nights min stay

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Beautiful restored farmhouse with swimming-pool situated in the heart of the Chianti Classico area, a few kilometers away from Castellina in Chianti. This property is quietly situated on a large 220-hectare farming estate producing excellent wines. Tastefully furnished,  …see more

from £379 / night

£2648 - £3009 / week

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from £379 / night

(5) Excellent 

1 / 56

Villa di Geggiano - Siena guest house sleeps 4

Province of Siena / Siena

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 60 km; Great for children of all ages ; Car advised;
One of the original, charming and elegant garden pavilions, situated within the garden of Villa di Geggiano, has recently been renovated into two luxury suites which have now been opened to guests for reservation. The Pavilion has a total capacity of 4 persons but it  …see more

from £375 / night

£2292 / week

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from £375 / night

1 / 57

Casale Bettolle - Bettolle villa sleeps 22

Sinalunga / Bettolle

11 bedroomsSleeps 22Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
Originally a country estate dating back to 1795, this superb Leopoldine villa blends outstanding elegance and comfort with traditional rustic features which reflect its long history. It retains the typical rooftop pigeon-loft, now romantically transformed into an extra-  …see more

from £1022 / night

£4584 - £6771 / week

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from £1022 / night

(1) Excellent 

1 / 18

Province of Siena / Siena

1 bedroomSleeps 32 nights min stay

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

from £75 / night

£459 - £634 / week

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from £75 / night

1 / 100

Milena - Castelnuovo Berardenga villa sleeps 18

Province of Siena / Castelnuovo Berardenga

9 bedroomsSleeps 183 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 3 nights min stay
Key info: Nearest beach 117 km; Swimming pool; Great for children of all ages ;
ExteriorsTuscany is equal to green, rolling hills, vineyards and olive groves, tradition, enchantment and hospitality. Cities of art such as Florence, Siena and Perugia are very close to the estate, which guarantees the chance for guests to discover more of the Italian  …see more

from £984 / night

£6875 / week

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from £984 / night

1 / 100

Casa Filippo - Colomba - Monteroni d'Arbia apartment sleeps 5

Province of Siena / Monteroni d'Arbia

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
This beautiful cottage has a warm fireplace, air conditioning, satellite TV, and a breathtaking view of the Val d'Arbia. The master bedroom has a king-size bed and an en suite bathroom with a shower. A second king-size bed is located on the upper loft, along with a  …see more

from £167 / night

£1084 - £1500 / week

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from £167 / night

1 / 12

Pienza / Monticchiello

2 bedroomsSleeps 21 night min stay

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

from £82 / night

£359 / week

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from £82 / night

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