Air conditioned apartments and villas to rent in Province of Siena

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937 Holiday homes

Filters applied: Air conditioning (940)

(5) Excellent 

15

Poggibonsi / Staggia Senese

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £78 / night

£544 / week

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from £78 / night

(6) Very Good 

56

Torrita di Siena / Montefollonico

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £190 / night

£949 / week

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from £190 / night

(1) Excellent 

29

Province of Siena / Montepulciano

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £233 / night

£1207 - £1897 / week

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from £233 / night

100

Emma - Olivo - Bagno Vignoni apartment sleeps 6

Province of Siena / Bagno Vignoni

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Olivo apartment is situated on the first floor of this lovely farmhouse. It is decorated in a delightful, traditional style with pretty floral fabrics and sunny colours to make you feel welcome. The original wooden beams and terracotta tiled flooring have also been kept  …see more

from £104 / night

£604 - £845 / week

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from £104 / night

(1) Good 

10

H 9 - Gaiole in Chianti apartment sleeps 5

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • 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 £87 / night

£388 / week

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from £87 / night

(6) Excellent 

56

Villa di Geggiano - Siena guest house sleeps 4

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning
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 £388 / night

£2371 / week

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from £388 / night

22

Villa Gaiole - Siena villa sleeps 13

Province of Siena / Siena

5 13 2 nights min

  • 5 bedrooms
  • Sleeps 13
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 £2561 / night

£8534 - £11378 / week

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from £2561 / night

(1) Excellent 

20

Casa Giardino - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
A cosy and lovingly furnished 1 bedroom apartment 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 wonderful SienaT  …see more

from £45 / night

£311 - £535 / week

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from £45 / night

(4) Excellent 

44

I MELOGRANI I:5 BDR Tuscan villa,view,pool ,WiFi - San Giovanni d'Asso villa sleeps 10

Province of Siena / San Giovanni d'Asso

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
You could not ask for a more special place in which to celebrate an important anniversary or simply spend a vacation with your family and friends ! I Melograni is a beautiful antique,indipendent, "casale" with a large fenced swimming pool (5x12 mt), 1km away (walking  …see more

from £468 / night

£3276 - £4225 / week

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from £468 / night

16

Galassia H - Gaiole in Chianti house sleeps 5

Province of Siena / Gaiole in Chianti

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden
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 £87 / night

£432 / week

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from £87 / night

(1) Excellent 

6

Province of Siena / Pienza

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £121 / night

£475 / week

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from £121 / night

(1) Very Good 

10

apartment "Il Campo" in Siena - Siena apartment sleeps 4

Province of Siena / Siena

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
The theme of this apartment (65sqm) is the incomparable main square of Siena, "Piazza del Campo". Situated on the 2nd floor of my historical Villa, a a splendid aristocratic building from the first part of the C17th - just 1.6 km from the pedestrian historical centre o  …see more

from £104 / night

£707 - £1035 / week

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from £104 / night

(1) Excellent 

13

Province of Siena / Asciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £95 / night

£647 - £914 / week

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from £95 / night

5

Province of Siena / Pienza

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £113 / night

£604 / week

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from £113 / night

24

San Casciano dei Bagni / Celle sul Rigo

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly

 …see more

from £69 / night

£302 / week

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from £69 / 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 £234 / night

£1638 - £1983 / week

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from £234 / night

27

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £179 / night

£1250 - £1682 / week

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from £179 / night

20

house and wonderful garden of exclusive use - Torri villa sleeps 4

Sovicille / Torri

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
“Il Molino" was restructured in 2011 applying great care of the particulars; entirely surrounded with a wide wonderful garden, the complex lies in a very quite and immaculate wood between the Chianti hills. It is only 25 minutes by car or by train far from the ce  …see more

from £78 / night

£432 / week

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from £78 / night

(5) Very Good 

15

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from £51 / night

£345 - £563 / week

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from £51 / 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

(3) Very Good 

28

Province of Siena / Castelnuovo Berardenga

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Air conditioning

 …see more

from £60 / night

£417 / week

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from £60 / night

18

Gorgeous, Fully Renovated Town Home - Cetona townhouse sleeps 7

Province of Siena / Cetona

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
The property owners are an engineer and a journalist. he property was restructured by two highly respected Roman architects, who painstakingly completed a restoration (in 2009) of this beautiful & unique town-home in the medieval Tuscan hillside town of Cetona (ca  …see more

from £61 / night

£475 / week

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from £61 / night

32

Leccetino - Trequanda villa sleeps 6

Province of Siena / Trequanda

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Villa Leccetino Tuscany Arriving at Leccetino, down a short tree covered road is like arriving at a very secret location. Tucked into the hillside surrounded by olive trees, this is a spectacular masonry villa, made with stones dug up from the ground on this terraced p  …see more

from £278 / night

£1940 - £3440 / week

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from £278 / night

22

Villa Baiocco - Chiusi villa sleeps 14

Province of Siena / Chiusi

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Villa Baiocco is a typical Tuscan, historic farm house from 1700, recently converted to a prestigious holiday home - without losing its unique character and charm. Surrounded by 20'000m2 of well kept gardens, for your private use only, it offers all the peace and t  …see more

from £246 / night

£1725 - £3880 / week

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from £246 / night

(3) Excellent 

22

SIENA,villa,pool,tennis,relax,near Piazza IL CAMPO - Siena villa sleeps 5

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
La villa (5 posti letto ) è situata nella campagna di Siena a circa 15 minuti a piedi dalla famosa 'Piazza del Campo' di Siena. Si trova in cima ad una collina, corredata di piscina e campo da tennis, offre splendidi panorami sulla città e sulla campagna cir  …see more

from £255 / night

£992 - £1725 / week

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from £255 / night

100

Petit Verdot - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
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 pool. All ar  …see more

from £435 / night

£3044 - £3392 / week

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from £435 / night

20

Province of Siena / Monteriggioni

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Air conditioning

 …see more

from £37 / night

£259 / week

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from £37 / night

(4) Very Good 

14

RONDINE apartment in beautiful countryside - Poggibonsi apartment sleeps 3

Province of Siena / Poggibonsi

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Podere Oliveta , which translates as ' Olivegrove farm', offers the Rondine apartment which enjoy a pretty location up in the hills near Gavignano, about 10 km east of S.Gimignano. The apartment has its own independent entrance and own garden area with barb  …see more

from £52 / night

£363 / week

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from £52 / night

(3) Excellent 

20

Granaio 7 - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 6 people (4+2) in total. The apartment is next to Granaio nr 6 (nr 277512) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San Gimignan  …see more

from £35 / night

£242 - £828 / week

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from £35 / night

25

Lodge Melograno wonderful view in Val D'Orcia - Pienza lodge sleeps 2

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Air conditioning
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £56 / night

£392 - £740 / week

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from £56 / night

22

Province of Siena / Pienza

3 2 1 night min

  • 3 bedrooms
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £91 / night

£544 / week

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from £91 / night

10

Province of Siena / Sinalunga

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £259 / night

£1811 / week

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from £259 / night

(3) Very Good 

20

Lovely and little panoramic "Mansarda" - Monticiano apartment sleeps 5

Province of Siena / Monticiano

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Nearest beach 65 km
  • Child friendly
  • Air conditioning
The apartment (60m2 - approx. 600 sqf) is located on the top floor and is made up of 4 beautifully-decorated rooms with a light blue pastel colour motif.The holiday flat has one double bedroom, with ample storage space and in the living room there is a double sofabed.  …see more

from £61 / night

£388 - £509 / week

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from £61 / night

(1) Very Good 

4

Province of Siena / Chiusi

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Air conditioning

 …see more

from £78 / night

£432 / week

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from £78 / night

(3) Very Good 

17

Province of Siena / Siena

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning

 …see more

from £87 / night

£561 / week

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from £87 / night

12

Montalcino / Val d'Orcia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

 …see more

from £104 / night

£690 / week

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from £104 / night

23

Fonte Senesi - Pienza villa sleeps 12

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa la Fonte is situated in the marvellous Val d'Orcia, the valley of the Sienese Crete.An ancient farmhouse dating back to 1846 that lies in an agricultural farm that extends over a surface of 150 hectares. Every year our olive grove produces a tasty oil that ca  …see more

from £548 / night

£3832 - £4436 / week

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from £548 / night

12

Province of Siena / Radicofani

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £52 / night

£302 / week

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from £52 / night

100

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

Province of Siena / Monteroni d'Arbia

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
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  …see more

from £242 / night

£1552 / week

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from £242 / night

(2) Excellent 

24

Stunning Villa in Siena with exclusive spa - Siena villa sleeps 10

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful villa in Siena with private Spa-Wellness Center room is situated on the hills with a breathtaking view over the vineyards up to Siena. An ideal accommodation for all those seeking peace and quiet but also a perfect point of departure for visiting the beau  …see more

from £234 / night

£1638 - £3447 / week

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from £234 / night

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