Air conditioned apartments and villas to rent in Province of Siena

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Province of Siena

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884 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.

(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) Very Good 

7

Castelnuovo Berardenga / Pianella

6 20 Min stay varies

  • 6 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

(1) Very Good 

31

Montisi holiday villa rental

Province of Siena / Montisi

5 6 Min stay varies

  • 5 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
We offer a relaxed holiday, You can lounge by the pool soaking up the sun or visit the many cities of intrest Siena, Florence and Rome are all very close. And of course the local places of Intrest. The spa, Pienze home of the English Patient and within view of your home  …see more

from £128 / night

£851 - £1535 / week

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from £128 / night

Featured properties

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
La camera e' molto accogliente e dotata di ogni comodità per rilassarsi in assoluta privacy . La nostra deliziosa colazione non è inclusa nel prezzo , ma ve la potremo includere con un supplemento . Qualora abbiate necessità particolari , non  …see more

from £86 / night

£599 / week

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from £86 / 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

21

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 £128 / night

£595 - £1107 / week

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from £128 / 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

32

Holiday villa rental

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 £488 / night

£3411 / week

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from £488 / night

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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Pricing unknown

9

Province of Siena / Torrita di Siena

8 20 1 night min

  • 8 bedrooms
  • Sleeps 20
  • 1 night min
  • Air conditioning
  • Ask about pets
  • Private garden

 …see more

from £77 / night

£522 / week

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from £77 / night

10

Province of Siena / Montepulciano

13 27 2 nights min

  • 13 bedrooms
  • Sleeps 27
  • 2 nights min
  • Swimming pool
  • Air conditioning

 …see more

from £112 / night

£642 / week

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from £112 / night

20

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
Orange triple bedroom with queen size bed, single bed, bathroom with shower, toilet, hairdryer, courtesy set, air conditioning, Wi-Fi, TV in room upon request.  …see more

from £66 / night

£461 / week

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from £66 / 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 £129 / night

£513 - £599 / week

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from £129 / night

24

Siena / Sant Andrea a Montecchio

1 4 2 nights min

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

 …see more

from £90 / night

£629 / week

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from £90 / 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

(12) Excellent 

50

Holiday villa with indoor pool, golf nearby in Gaiole in Chianti

Gaiole in Chianti / Montefienali

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SERVICES INCLUDED • Cleaning pre-arrival and post-departure • Meet and greet by local member of staff • Daily cleaning Monday to Friday: 2 hours per day • Complete change of all sheets and towels every Saturday (a full spare set of bathroom towels i  …see more

from £693 / night

£4847 - £7150 / week

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from £693 / night

(1) Excellent 

23

Province of Siena / Siena

3 10 1 night min

  • 3 bedrooms
  • Sleeps 10
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £112 / night

£778 / week

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from £112 / 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

(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

(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

£471 - £650 / week

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from £77 / night

(8) Excellent 

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 £342 / night

£1710 / week

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from £342 / 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 £90 / night

£539 / week

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from £90 / night

16

Province of Siena / Asciano

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £59 / night

£413 / week

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from £59 / 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 £428 / night

£2565 / week

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from £428 / night

24

Monticiano / Tocchi

1 5 5 nights min

  • 1 bedroom
  • Sleeps 5
  • 5 nights min
  • Nearest beach 39 km
  • Suitable for children age 5+
  • Air conditioning

 …see more

from £77 / night

£513 - £962 / week

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from £77 / night

22

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Every apartment has its own outside space with table and chairs for outside eating (directly in front of the entrance of the apartments) and offer a fantastic panorama over the whole valley of the river Elsa.<br />enfant bed  …see more

from £98 / night

£684 - £898 / week

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from £98 / night

16

Province of Siena / Castiglione D'Orcia

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £52 / night

£718 - £2154 / week

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from £52 / night

5

Province of Siena / Rapolano Terme

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £59 / night

£413 / week

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from £59 / night

24

Montalcino / Val d'Orcia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from £197 / night

£1377 / week

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from £197 / night

(4) Excellent 

19

Siena holiday apartment rental

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
Appartamento bello ed elegante appena ristrutturato ed arredato di nuovo, vicino al centro storico della città. Nella zona notte soffitti con travi a vista, nella tipica tradizione toscana. Composto da ampia cucina/soggiorno, camera matrimoniale, camera di passag  …see more

from £69 / night

£428 - £667 / week

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from £69 / 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; 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 centre of Florence.  …see more

from £77 / night

£428 / week

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from £77 / night

(1) Excellent 

21

Holiday b&b letting

Province of Siena / Rapolano Terme

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
Mint triple bedroom with queen size bed, single bed, bathroom with shower, toilet, hairdryer, courtesy set, air conditioning, Wi-Fi, TV in room upon request.  …see more

from £66 / night

£461 / week

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from £66 / 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 £86 / night

£556 / week

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from £86 / night

10

Province of Siena / San Gimignano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 80 km
  • Car not necessary
  • Air conditioning

 …see more

from £60 / night

£419 / week

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from £60 / night

18

Rapolano Terme holiday b&b rental

Province of Siena / Rapolano Terme

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Lavender quadruple bedroom with queen size bed, two single beds, bathroom with shower, toilet, hairdryer, courtesy set, air conditioning, Wi-Fi, TV in room upon request.  …see more

from £77 / night

£533 / week

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from £77 / night

(1) Excellent 

5

Province of Siena / Trequanda

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly

 …see more

Pricing unknown

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Pricing unknown

(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 £180 / night

£1257 / week

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from £180 / night

4

Holiday apartment in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets
Thanks to the “Self-catering Formula” our guests will feel like they're at home, the equipments of every flat are really complete.<br />The position in the heart of Chianti makes Resort Olmo a privileged starting point to explore Tuscany.  …see more

Pricing unknown

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Pricing unknown

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

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 £245 / night

£1710 - £5855 / week

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from £245 / night