Air conditioned apartments and villas to rent in Province of Siena

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Province of Siena

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903 Holiday homes

Filters applied: Air conditioning

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

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 £52 / night

£308 / week

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from £52 / 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

£342 - £558 / week

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from £51 / night

(2) Very Good 

19

Montalcino holiday studio rental

Province of Siena / Montalcino

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Air conditioning
One large and cosy suite with a high ceiling with the typical wooden beams and wooden floor. There's a fully equipped kitchen, a small sitting area, a double bed with a restored big old Tuscan wardrobe. The private bathroom is with shower in travertine. The suite i  …see more

from £142 / night

£988 / week

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from £142 / night

Featured properties

25

Pienza holiday lodge rental

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 £73 / night

£509 - £808 / week

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from £73 / 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 £112 / night

£599 / week

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from £112 / night

17

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights 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. l  …see more

from £112 / night

£676 / week

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from £112 / night

25

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

 …see more

from £112 / night

£778 / week

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from £112 / night

(2) Excellent 

17

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful holiday resort near Montepulciano and Pienza  …see more

from £95 / night

£539 - £988 / week

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from £95 / night

(4) Very Good 

7

Province of Siena / Siena

1 2 Min stay varies

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

 …see more

from £51 / night

£353 / week

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from £51 / night

26

Holiday home with shared pool in Casole d'Elsa

Casole d'Elsa / Monteguidi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
This charming and carefully restored farmhouse is privately set on the property grounds. It is spacious and elegantly furnished, whilst also retaining original features like exposed stonework and chestnut beam ceilings. It develops over 2 floors, comprising of 3 bedroom  …see more

from £95 / night

£662 - £1267 / week

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from £95 / night

(1) Excellent 

20

Gaiole in Chianti holiday apartment rental

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
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 £44 / night

£306 - £335 / week

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from £44 / night

(3) Very Good 

24

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
“Well-located and roomy house” We were 10 adults and two children (three generations) spending one week at the house in May of 2014. We found the house very suitable (for five couples) since it had five large bedrooms. It was very convenient that each  …see more

from £232 / night

£1624 - £2906 / week

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from £232 / night

(9) Excellent 

57

Holiday lodge in Pienza

Province of Siena / Pienza

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
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 £218 / night

£1526 - £2783 / week

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from £218 / night

(6) Very Good 

23

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 0 km
  • Swimming pool
  • Child friendly
“Peaceful taste of Tuscany!!!!” Stayed here for a lovely, idyllic, December week. Amazing apartment with all home comforts. Loved walking through the village, stopping for pizza and fine wines :-) The views over the hills and vineyards are incredibly i  …see more

from £150 / night

£600 / week

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from £150 / night

24

Pienza / Monticchiello

1 2 1 night min

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

 …see more

from £63 / night

£334 / week

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from £63 / night

16

Siena / Sant Andrea a Montecchio

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £60 / night

£416 / week

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from £60 / night

26

Villa rental in Sant'Albino with swimming pool

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 £257 / night

£1795 - £3077 / week

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from £257 / night

(3) Excellent 

22

Holiday villa rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Centrum of city only 15 minutes by foot ! The villa was perfectly clean when we arrived. The kitchen is well equipped and fun to cook in.We highly recommend this property for those who are looking for a peaceful setting near all that Siena has to offer.  …see more

from £253 / night

£1069 - £2265 / week

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from £253 / night

27

Casole d'Elsa holiday apartment rental

Casole d'Elsa / Monteguidi

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 70 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. The Etruscan hills surrounding the property are but a short distance from the most celeb  …see more

from £90 / night

£628 - £1123 / week

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from £90 / night

(1) Very Good 

39

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £102 / night

£594 - £742 / week

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from £102 / night

18

Holiday apartment in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 85 km
  • Child friendly
  • Car not necessary
Brown apartment Central and cosy apartment with double bedroom, bathroom with shower, large living area with sofa bed, equipped kitchen, private equipped garden, free WIFI, TV, air conditioning.<br />Upon request as extra services: cooking classes, wine tours, e  …see more

from £52 / night

£359 / week

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from £52 / night

17

Province of Siena / Montisi

7 14 1 night min

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

 …see more

from £77 / night

£539 / week

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from £77 / 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 £76 / night

£526 - £1500 / week

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from £76 / night

(1) Very Good 

10

Holiday apartment in Siena

Province of Siena / Siena

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
There is a shopping area 500 meters away from the apartment: 3 supermarkets, shops, coffee, bar, bakery..  …see more

from £103 / night

£701 - £1026 / week

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from £103 / night

7

Pancole holiday farmhouse rental

San Gimignano / Pancole

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
francigena, San Gimignano, Pool, Garden, relax, peace, privacy, Tuscuny, Chianti, Chiantishire, Vernaccia,<br />The apt Tramonto is located on the first floor. From its windows you can admire wide landscape toward west.  …see more

from £59 / night

£385 - £471 / week

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from £59 / 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 £69 / night

£445 - £842 / week

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from £69 / night

(1) Excellent 

13

Holiday villa with shared pool, golf nearby in Sovicille

Province of Siena / Sovicille

3 4 3 nights min

  • 3 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 68 km
  • Swimming pool
  • Air conditioning
The holiday home "Il Rifugio del Falconiere" offers an elegant villa of 220 square meters with a large living room, where there is a fireplace and a unique décor, a large dining room, a fully equipped kitchen with dishwasher, refrigerator that produces  …see more

from £424 / night

£2967 / week

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from £424 / night

25

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

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

 …see more

from £89 / night

£689 / week

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from £89 / night

22

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

(2) Excellent 

12

Rapolano Terme / Serre di Rapolano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 110 km
  • Child friendly
  • Air conditioning

 …see more

from £60 / night

£342 - £522 / week

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from £60 / night

(3) Excellent 

12

Farmhouse rental in Val di Merse

Siena / Val di Merse

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
The property PODERE SORTOIANO dates back to the 14th century and for generations has been part of the property Santini, once farmers. The apartments, as well as the "hut" were once stables for livestock. It has now been restored by the Santini family with much  …see more

from £48 / night

£317 - £377 / week

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from £48 / night

(1) Excellent 

32

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect.” The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arri  …see more

from £278 / night

£1949 - £2513 / week

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from £278 / night

(1) Excellent 

99

Province of Siena / San Gimignano

1 4 Min stay varies

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

 …see more

from £107 / night

£659 - £983 / week

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from £107 / night

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 £89 / night

£599 - £1616 / week

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from £89 / night

7

Province of Siena / Casole d'Elsa

1 4 Min stay varies

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

 …see more

from £75 / night

£453 - £830 / week

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from £75 / night

(1) Excellent 

37

Holiday lodge with shared pool in Pienza

Province of Siena / Pienza

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
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 £116 / night

£808 - £1406 / week

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from £116 / night

13

Holiday apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Casa al bosco” is an elegant house restored in the second half of the 1800s. It is situated in a property of approximately 12 hectares where there are olive trees and a vineyard.  …see more

Pricing unknown

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Pricing unknown

(2) Excellent 

24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa in Siena with SPA room and swimming pool at exclusive use.  …see more

from £232 / night

£1624 - £3418 / week

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from £232 / night

5

Province of Siena / Rapolano Terme

1 2 1 night min

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

 …see more

from £77 / night

£539 - £599 / week

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from £77 / night

(14) Excellent 

24

San Gimignano holiday villa rental

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
“Beautiful!” Four of us stayed here in October 2012, the house is beautiful and immaculately maintained as are the gardens. Unfortunately the weather wasn't on our side so we didn't spend as much time in the garden as we'd have liked but you could spe  …see more

from £69 / night

£471 - £1539 / week

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from £69 / night