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.

12

Cedda holiday apartment rental

Poggibonsi / Cedda

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
1 Double room with a double bed, 1 double room, living room in the little tower, kitchen, bathroom, over two floors.  …see more

from £75 / night

£520 - £650 / week

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from £75 / 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 £251 / night

£1755 - £6009 / week

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from £251 / 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 £36 / night

£308 / week

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from £36 / night

Featured properties

15

Holiday cottage with golf nearby in Sinalunga

Province of Siena / Sinalunga

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
An intimate and fully equipped flat in the heart of the old town of Sinalunga.Ideal for relaxing.  …see more

Pricing unknown

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Pricing unknown

(2) Very Good 

24

Holiday villa rental

Montalcino / Val d'Orcia

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great location, fits all types of travellers specially family reunions” The Villa is placed in a very special and beautiful area in the Tuscany region. Near (up to 1h - 1.20h) many special places and famous cities, such as Siena and Montalcino. The a  …see more

Pricing unknown

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Pricing unknown

11

Cedda holiday apartment rental

Poggibonsi / Cedda

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
1 double room with a double bed, 1 double room, living room with double sofa bed, kitchen, bathroom. First floor. No heating system. 112 sqm.  …see more

from £75 / night

£520 - £650 / week

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from £75 / night

5

B&b rental in Rapolano Terme with shared pool

Province of Siena / Rapolano Terme

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Romantica camera matrimoniale/doppia con possibilità di aggiungere un letto extra per una terza persona,bagno con doccia e balcone privato con tavolo e sedie per il relax . La camera e' molto accogliente e dotata di ogni comodità per rilassarsi in as  …see more

from £88 / night

£615 / week

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from £88 / night

100

Holiday villa with swimming pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 117 km
  • Swimming pool
  • Child friendly
This villa is large and boasts a wonderful and typical Tuscan style. It sleeps up to 18 people, and it affords all the modern comforts and facilities needed for a perfect stay. It can also be rented for weddings and other events.  …see more

from £1036 / night

£7237 - £8009 / week

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from £1036 / night

16

Province of Siena / Castellina In Chianti

9 16 Min stay varies

  • 9 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

16

Contignano holiday villa rental

Radicofani / Contignano

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The exquisite villa is located in Contignano surrounded by spectacular views of rolling clay hills and countryside. The villa sleeps up to 19 in 8 very spacious bedrooms, 2 twins, 5 doubles and a lofted bedroom containing a sofa bed, a twin and a double bed  …see more

Pricing unknown

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Pricing unknown

(2) Excellent 

12

Province of Siena / Monteriggioni

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

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 £439 / night

£2632 / week

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from £439 / 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 £71 / night

£308 / week

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from £71 / 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 £264 / night

£1843 / week

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from £264 / night

65

Holiday villa letting

Province of Siena / Monteroni d'Arbia

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p>Large air conditioned villa near Siena - Villa Santa Caterina is an imposing fully restored 13th-century monastery, subsequently used as a farmhouse, which has been transformed into an elegant country holiday house.</p>  …see more

from £1612 / night

£11280 - £16940 / week

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from £1612 / night

26

Province of Siena / Siena

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 80 km
  • Child friendly
  • Air conditioning

 …see more

from £88 / night

£571 / week

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from £88 / night

10

Holiday apartment with shared pool in Murlo

Murlo / Casciano di Murlo

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
We offer our guests secluded luxury close to most historic and picturesque towns of Siena, Pienza, Montalcino, Montepulciano and many others. Air conditioning, internet wi-fi, panoramic views, swimmingpool. The nearby Casciano di Murlo offers all kind of services.<br  …see more

Pricing unknown

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Pricing unknown

16

Holiday b&b rental

Gaiole in Chianti / Lecchi

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 95 km
  • Swimming pool
  • Car not necessary
Adjacent apartment with terra-cotta floors and furnished with a double Chianti iron bed (subsequently with a madonna picture above), a large armadio and an en suite bathroom. Through French doors the room leads to a 55 square meter terrace with an antique iron sofa, a f  …see more

from £97 / night

£527 / week

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from £97 / night

(2) Excellent 

28

Apartment rental in Siena

Province of Siena / Siena

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
2 bedrooms apartments in the historical centre od Siena. Very close to Piazza del Campo, Duomo, museums, supermarket, bus station and reastaurant.  …see more

from £87 / night

£834 - £1294 / week

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from £87 / night

19

Province of Siena / Gaiole in Chianti

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from £369 / night

£1316 / week

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from £369 / night

40

Apartment rental in Monteriggioni with shared pool

Province of Siena / Monteriggioni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 84 km
  • Swimming pool
  • Child friendly
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation.Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. <br />In our restaurant is possible to take:BreakfastDinnerWine tastin  …see more

Pricing unknown

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Pricing unknown

19

Province of Siena / Siena

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 80 km
  • Child friendly
  • Air conditioning

 …see more

from £71 / night

£461 / week

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from £71 / night

20

Holiday villa rental

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 th  …see more

from £79 / night

£439 / week

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from £79 / 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 £464 / night

£3246 - £6097 / week

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from £464 / night

101

Holiday apartment with shared pool in Bagno Vignoni

Province of Siena / Bagno Vignoni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • 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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Pricing unknown

10

Province of Siena / Rapolano Terme

4 8 Min stay varies

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

 …see more

Pricing unknown

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Pricing unknown

21

Holiday villa with swimming pool in Valiano

Montepulciano / Valiano

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
Villa located on top of a hill and dipped between wineyards.Due to its strategic position, in Valiano di Montepulciano, half way from Rome to Florence and on the border between Tuscany and Umbria region, it will be easy to visit the most artistic towns in Italy  …see more

from £627 / night

£3948 / week

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from £627 / night

21

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 80 km
  • Child friendly
  • Air conditioning

 …see more

from £97 / night

£615 / week

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from £97 / night

9

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 £93 / night

£527 - £965 / week

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from £93 / night

38

Apartment rental in Monteriggioni with shared pool

Province of Siena / Monteriggioni

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 84 km
  • Swimming pool
  • Child friendly
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation.Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. <br />In our restaurant is possible to take:BreakfastDinnerWine tasting  …see more

Pricing unknown

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Pricing unknown

16

Contignano holiday villa rental

Radicofani / Contignano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annex. It is surrounded by breathtaking views over the Italian countryside  …see more

Pricing unknown

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Pricing unknown

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 £53 / night

£308 / week

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from £53 / night

23

Siena / Isola d'Arbia

2 6 Min stay varies

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

 …see more

from £108 / night

£473 - £1235 / week

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from £108 / night

100

Holiday apartment rental

Province of Siena / Bagno Vignoni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • 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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Pricing unknown

(1) Average 

10

Gaiole in Chianti holiday apartment rental

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 £88 / night

£395 / week

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from £88 / night

24

Province of Siena / Murlo

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

11

Pienza / Monticchiello

2 5 1 night min

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

 …see more

from £106 / night

£632 / week

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from £106 / 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 £68 / night

£473 / week

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from £68 / night

(2) Excellent 

14

Province of Siena / Monteriggioni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly

 …see more

Pricing unknown

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Pricing unknown

13

Holiday villa with shared pool in Montisi

Province of Siena / Montisi

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Beautiful Three bedroom stone house spread over three floors with the master bedroom on the top floorentered by a spiral staricase.Fully fitted kitchen with fridge freezr, dishwasher, oven and hob with all of the cooking equipment supplied.  …see more

from £131 / night

£873 - £1575 / week

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from £131 / night