Air conditioned apartments and villas to rent in Province of Siena

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Province of Siena

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932 Holiday homes

Filters applied: Air conditioning (967)

Travellers going to Province of Siena are booking June dates now. Secure your holiday home today and have the perfect trip.

28

Holiday apartment in Quercegrossa

Monteriggioni / Quercegrossa

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Villa is situated in a splendid 18th century mansion, with typical Sienese architecture. The property position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena (6 km away).The mansion is s  …see more

from £92 / night

£615 - £1658 / week

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from £92 / night

(1) Very Good 

16

Holiday villa with swimming pool, golf nearby in Larniano

San Gimignano / Larniano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Not far from Siena, for 5 minutes along the road from San Gimignano goes towards Gambassi, we find the gates of Villa Panorama.It is an old building of more than 5 centuries and tastefully decorated and with quality furniture and style typical of the villas in Tuscany  …see more

from £220 / night

£1536 - £2193 / week

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from £220 / night

(3) Very Good 

24

Holiday villa with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly
Located within walking distance of the village of Gaiole in Chianti, the villa offers the perfect setting to explore the Chianti Classico region, enjoy the breathtaking views of the vineyards and olive groves, and experience the charming Tuscan lifestyle.<br />Bea  …see more

from £86 / night

£597 - £683 / week

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from £86 / night

Featured properties

23

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 can be tasted and purchased during your stay.  …see more

from £538 / night

£3764 - £5150 / week

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from £538 / night

(3) Very Good 

20

Holiday apartment in Monticiano

Province of Siena / Monticiano

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Nearest beach 65 km
  • Child friendly
  • Air conditioning
Toscana, Tuscany, SanGalgano, Monticiano, Siena, Firenze, Pisa, Volterra, Holidays, garden,<br />SPECIAL PRICE IS FOR 1 PERSON  …see more

from £62 / night

£395 - £518 / week

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from £62 / night

27

Province of Siena / Sarteano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £1058 / night

£7400 / week

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from £1058 / night

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children age 5+
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany.<b  …see more

from £49 / night

£343 - £465 / week

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from £49 / night

12

Pienza / Monticchiello

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Air conditioning

 …see more

from £86 / night

£378 / week

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from £86 / night

100

Holiday villa with swimming pool in Province of Siena

Tuscany / Province of Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
This is an ample villa sleeping up to 12 people, fully fitted and featuring its own garden and swimming pool. Cities such as Pisa and Florence are nearby, and that makes this large villa a perfect starting point for exploring the entire Tuscan region  …see more

from £264 / night

£1036 - £1737 / week

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from £264 / night

19

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Air conditioning
  • Private garden
Cottage in the tuscan countryside close to Siena and Florence, in the Chianti shire. Typical tuscan style and very comfortable place. Swimming pool and huge garden.  …see more

from £609 / night

£4259 - £4496 / week

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from £609 / night

19

Holiday studio in Siena

Province of Siena / Siena

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
Located on the hills of central Tuscany, at only 1,5 km from the walls of Siena, this charming holiday accommodation has been totally restored into 6 comfortable self-catering apartments with high quality furniture. All the holiday apartments have independent entrances  …see more

from £72 / night

£413 - £540 / week

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from £72 / night

(1) Excellent 

12

Pontignano holiday apartment rental

Castelnuovo Berardenga / Pontignano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
The tranquility, the beauty of Chianti, the quality of the products that come from this land, the view that you can enjoy a walk around the farmhouse, make the farmhouse Pontignanello unique and unforgettable.  …see more

from £55 / night

£381 / week

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from £55 / night

24

Villa rental in San Giovanni d'Asso with swimming pool

Province of Siena / San Giovanni d'Asso

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p><span class="x_style25">Centred around a pretty garden, Casa Vittorio is a notable, historic residence set over several levels and elegantly furnished. It is in a village location, just a short stroll from a restaurant, the castle and the truffl  …see more

from £686 / night

£4800 - £5850 / week

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from £686 / night

21

Castelnuovo Berardenga / Pianella

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

19

Holiday apartment in Casaglia

San Gimignano / Casaglia

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the elegantly renovated barn, Iris is particularly spacious and filled with natural light.<br />Baby bed on request is free  …see more

from £131 / night

£844 - £1159 / week

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from £131 / night

27

Apartment rental in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 96 km
  • Suitable for children age 5+
  • Car not necessary
This cosy, typical Sienese two bedroom apartment for 2 to 4 people is located in the historic city center of Siena approx. 300 meters distant from „Piazza del Campo“. All the main attractions of the historic centre are within walking distance. Public parkin  …see more

from £84 / night

£584 - £805 / week

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from £84 / night

(1) Excellent 

23

Holiday farmhouse with shared pool in Buonconvento

Province of Siena / Buonconvento

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Great place for family and friends” We rented all three cottages for a group of 17 including small children and adults. We couldn't have asked for a better vacation. The area is beautiful, serene and relaxing. Having the pool there took the pressur  …see more

from £145 / night

£1141 / week

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from £145 / night

6

Province of Siena / Montepulciano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Air conditioning

 …see more

from £110 / night

£878 / week

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from £110 / night

20

Holiday manor house with swimming pool in Pienza

Province of Siena / Pienza

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Tenth century posting house which has kept its charm. Large garden with swimming pool.  …see more

from £657 / night

£4597 - £5746 / week

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from £657 / night

(1) Excellent 

31

Province of Siena / San Quirico d'Orcia

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £103 / night

£676 - £799 / week

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from £103 / night

(4) Excellent 

16

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

 …see more

from £79 / night

£422 - £983 / week

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from £79 / night

22

Holiday villa in Siena

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.  …see more

from £2699 / night

£8994 - £11361 / week

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from £2699 / night

19

Province of Siena / Colle di Val d'Elsa

3 4 2 nights min

  • 3 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from £58 / night

£400 / week

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from £58 / night

17

Holiday apartment in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Central, elegant apartment, tastefully furnished, large entrance with sitting area, dining area, equipped kitchen, bedroom with double bed, twin bedded bedroom, TV, WiFi in the common areas, Air conditioning available (not included).  …see more

from £119 / night

£829 / week

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from £119 / night

(15) Excellent 

23

Casole d'Elsa holiday villa rental

Province of Siena / Casole d'Elsa

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Villa Podere Scopicciolo is located about 30 miles from Florence. It is 900 ft above sea level in the heart of Tuscany surruonded by cultivated farm land and well preserved forests. It is fully immersed in the countryside enjoying peace and tranquillity, yet convenientl  …see more

from £869 / night

£6079 - £9211 / week

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from £869 / night

(7) Very Good 

32

Province of Siena / Siena

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £88 / night

£1579 / week

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from £88 / night

7

Province of Siena / Colle di Val d'Elsa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

(2) Excellent 

5

Province of Siena / Colle di Val d'Elsa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

100

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This property is a lovely villa set in Tuscany Italy. It has 2 bedrooms and 2 bathrooms, and it is perfect for those who are looking for a unique experience. This property features: a swimming Pool, air Conditioning .  …see more

from £171 / night

£1000 - £1668 / week

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from £171 / night

34

Sant'Albino holiday villa rental

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 ar  …see more

from £402 / night

£2808 - £5439 / week

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from £402 / night

(1) Excellent 

21

Province of Siena / Cetona

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Child friendly

 …see more

from £185 / night

£1290 / week

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from £185 / night

16

Holiday farmhouse in Crete Senesi

Asciano / Crete Senesi

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Apartment (3 bedrooms) in old Tuscan Cottage with panoramic view and swimming pool. Just restored and finely furnished with well equipped kitchens. Podere Sant'Alessandro is immersed in beautiful scenery, and is among woods, vineyards, medieval villages and castles  …see more

Pricing unknown

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Pricing unknown

17

Province of Siena / Montisi

7 14 1 night min

  • 7 bedrooms
  • Sleeps 14
  • 1 night min
  • Swimming pool
  • Air conditioning

 …see more

from £79 / night

£553 / week

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from £79 / night

6

Province of Siena / Chianciano Terme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

Pricing unknown

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Pricing unknown

20

Holiday apartment in Casaglia

San Gimignano / Casaglia

3 2 Min stay varies

  • 3 bedrooms
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the annex, Glicine is our largest apartment and probably the most private as it is detached from the main villa.It has one double bedroom (with king size bed), single bedroom for 2 child, one bathroom (with shower stall ), kitchen/living room<br />Baby  …see more

from £145 / night

£868 - £1207 / week

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from £145 / night

33

Murlo / Casciano di Murlo

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning

 …see more

from £53 / night

£316 / week

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from £53 / night

19

Apartment rental in Casole d'Elsa with shared pool

Casole d'Elsa / Monteguidi

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly
This charming farmhouse complex is the result of a recent and elegant restoration of a typical Tuscan country complex, near the town of Casole d'Elsa, in the province of Siena.  …see more

from £89 / night

£623 / week

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from £89 / night

(3) Very Good 

36

Holiday farmhouse with shared pool in Acquaviva di Montepulciano

Montepulciano / Acquaviva di Montepulciano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
FREE: wi-fi, parking, central heating, final cleaning, mountain bike, iron, air conditioning (bedrooms)  …see more

from £176 / night

£1141 / week

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from £176 / night

24

Montalcino / Val d'Orcia

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £176 / night

£1229 / week

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from £176 / night

(1) Excellent 

30

Province of Siena / San Gimignano

2 4 Min stay varies

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

 …see more

from £71 / night

£457 - £865 / week

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from £71 / night