Air conditioned apartments and villas to rent in Province of Siena

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Province of Siena

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888 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.

(1) Very Good 

24

Pienza / Monticchiello

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from £77 / night

£509 - £2111 / week

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from £77 / 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 £70 / night

£399 - £522 / week

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from £70 / night

20

Villa rental in Castiglione D'Orcia with swimming pool

Province of Siena / Castiglione D'Orcia

1 21 7 nights min

  • 1 bedroom
  • Sleeps 21
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Farmhouse divided into apartments set in 10 hectares of private forest and with a large swimming pool.<br />sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …see more

from £612 / night

£4280 - £6140 / week

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from £612 / night

Featured properties

24

Holiday apartment with shared pool in Gaiole in Chianti

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

26

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
On the ground floor to welcome the guests and for their use is a lounge with an open fireplace and a well equipped kitchen which leads to an external gazebo for dining al fresco and to enjoy cool evenings out in the open. Situated on the same level of the lounge and ope  …see more

from £424 / night

£2543 / week

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from £424 / night

29

Apartment letting in Siena

Province of Siena / Siena

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Charming holiday accommodation located just outside the walls of the historical center, with a 900 square meters private garden and a 30000 square meters private park, 7 minutes walk from Piazza del Campo, 3 minutes walk from Piazza San Francesco.  …see more

from £89 / night

£445 / week

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from £89 / night

10

Holiday farmhouse in San Fabiano

Monteroni d'Arbia / San Fabiano

4 16 Min stay varies

  • 4 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The Podere Podernovo offers accommodation up to 16 people ,with all comforts,as heating, air conditioning, Internet,wi-fi, Tv with Sky.The Count Fiorentini will welcome you in his farmhouse just 12 km south of Siena in the Arbia valley. You can rent the whole Podere the  …see more

from £458 / night

£2543 - £3390 / week

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from £458 / 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

18

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 £90 / night

£628 - £1043 / week

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from £90 / night

9

Apartment rental in Siena

Province of Siena / Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Suitable for children age 5+
  • Air conditioning
Siena Apartments with easy access to the town centre  …see more

from £64 / night

£403 - £522 / week

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from £64 / night

18

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Air conditioning
La naturale estensione del paese di Gaiole in Chianti. Il concetto del “villaggio - nel - villaggio” unico nel suo genere. Il concetto del borgo che diventa parte integrante del villaggio. Una cura maniacale dell' architettura e dei materiali. Disponibi  …see more

from £67 / night

£339 / week

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from £67 / night

(3) Average 

27

Apartment rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning
The apartments have been restored preserving the typical features of country houses, though equipped with every kind of comfort.Every flat differs from the other, but each is equipped with independent entrance and is composed as follows: living room with fully equip  …see more

from £102 / night

£678 / week

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from £102 / night

(3) Very Good 

36

Holiday farmhouse with shared pool in Acquaviva di Montepulciano

Montepulciano / Acquaviva di Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 £119 / night

£721 - £1272 / week

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from £119 / night

(1) Excellent 

27

Holiday farmhouse rental

Province of Siena / San Gimignano

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
House with two apartments near San Gimignano in TuscanyHoliday Apartment offers 2 flats communicating inside in 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 bedro  …see more

from £111 / night

£746 - £1356 / week

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from £111 / night

22

Montepulciano holiday villa rental

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
TUSCANY MONTEPULCIANO PIENZA ANCIENT COUNTRY FARM ENTIRE OR HALF PROPERTY WEEKLY RENT ONLY groups of 4-10 welcome<br />heating upon request extra fee to be paid at check out according to gasoline cube meters used  …see more

from £255 / night

£1780 / week

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from £255 / night

(1) Excellent 

13

Holiday apartment with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
The house is located in the heart of the Chianti Classico, inside the town of Gaiole in Chianti (all kinds of shops). The apartment is on the ground floor and is part of a building where the owners reside.Outside a portion of an equipped courtyard is available for t  …see more

from £34 / night

£297 / week

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from £34 / night

100

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in Tuscany Italy, this charming villa is the ideal place for your holidays. The villa offers: a swimming Pool, air Conditioning, an internet Connection .  …see more

from £364 / night

£2543 - £6611 / week

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from £364 / 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 £51 / night

£297 / week

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from £51 / night

(2) Very Good 

100

Castellina In Chianti holiday villa rental

Province of Siena / Castellina In Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This grand house, with 5 bedrooms and 5 bathrooms can host 10 people, so it is ideal for large families. Located in Tuscany Italy, this house offers a swimming Pool, an internet Connection .  …see more

from £334 / night

£1949 - £2918 / week

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from £334 / night

18

Rapolano Terme holiday b&b rental

Province of Siena / Rapolano Terme

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
Cherry triple bedroom with queen size bed, single bed, bathroom with shower, toilet, hairdryer, courtesy set, air conditioning, Tv upon request. check-in 14:00-18:00 check-out within 11:00 Breakfast included on week-end only. Sunday-Friday Italian breakfast Euro 5,00 p  …see more

from £66 / night

£457 / week

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from £66 / night

6

Holiday apartment in Siena

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
There is a shopping area 500 meters away from the apartment: 3 supermarkets, shops, coffee, bar, bakery..  …see more

from £77 / night

£509 - £636 / week

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from £77 / night

30

Holiday apartment with indoor pool in Pienza

Province of Siena / Pienza

8 15 7 nights min

  • 8 bedrooms
  • Sleeps 15
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely 18th century villa with swimming-pool in Val d'Orcia is located near Pienza, surrounded by the gently rolling hills of this magnificent countryside  …see more

from £448 / night

£3136 - £5890 / week

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from £448 / night

34

Holiday villa in Montepulciano

Province of Siena / Montepulciano

7 19 Min stay varies

  • 7 bedrooms
  • Sleeps 19
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Podere Monti is a 16th century farmhouse nestled between woods and olive groves. It has been turned into a residence of refined charm that retains its atmosphere of informal welcome. The guest rooms are few but exquisitely furnished; each one has its own unique charac  …see more

from £467 / night

£2712 - £5255 / week

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from £467 / night

22

Province of Siena / Colle di Val d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning

 …see more

from £128 / night

£509 - £594 / week

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from £128 / night

(5) Excellent 

31

Castelnuovo Berardenga / Pianella

2 5 3 nights min

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

 …see more

from £47 / night

£327 / week

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from £47 / night

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 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 - £365 / week

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from £44 / 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 £102 / night

£678 / week

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from £102 / night

(1) Excellent 

18

Province of Siena / Siena

1 3 2 nights min

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

 …see more

from £77 / night

£467 - £645 / week

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from £77 / night

21

Holiday apartment with shared pool in Montalcino

Province of Siena / Montalcino

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjo  …see more

from £170 / night

£1187 / week

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from £170 / night

45

Province of Siena / Montepulciano

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

Pricing unknown

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Pricing unknown

100

Holiday apartment with shared pool in Bagno Vignoni

Province of Siena / Bagno Vignoni

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
These apartments are situated in extensive parks including a swimming pool and lake in rural Tuscany. They can accommodate between 2 and 8 guests and are a short distance from famous historical towns such as Montepulciano, Pienza and Montichiello.  …see more

Pricing unknown

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18

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £85 / night

£594 / week

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from £85 / night

20

Villa rental in Pienza with swimming pool

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below.  …see more

from £480 / night

£3356 - £4450 / week

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from £480 / night

20

Holiday home in Buonconvento

Province of Siena / Buonconvento

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully restored 14th century farmhouse sits within a farming estate on a hilltop with magnificent views over the soft hills of the Arbia river valley.  …see more

from £943 / night

£3769 - £6086 / week

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from £943 / night

16

Montalcino holiday villa rental

Province of Siena / Montalcino

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
bibbianello is a classic stone farmhouse on the edge of the historic town of montalcino, home of the famous "brunello" wine. The house stands in a splendid and tranquil spot with a view of montalcino and of the surrounding countryside. It has been perfectly re  …see more

from £276 / night

£1932 - £3240 / week

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from £276 / night

12

Pienza / Monticchiello

2 2 1 night min

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

 …see more

from £84 / night

£365 / week

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from £84 / night

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 £520 / night

£3636 - £4975 / week

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from £520 / 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 £119 / night

£763 / week

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from £119 / night

28

Holiday villa in Pienza

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury Villa near Pienza, ideal for large families or friend's group.  …see more

from £243 / night

£1695 - £5806 / week

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from £243 / 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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