Air conditioned apartments and villas to rent in Province of Siena

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  • Asciano (21)
  • Bagno Vignoni (11)
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  • Casole d'Elsa (25)
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  • Chianciano Terme (4)
  • Chiusdino (2)
  • Chiusi (8)
  • Colle di Val d'Elsa (15)
  • Gaiole in Chianti (52)
  • Le Piazze (2)
  • Montalcino (45)
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  • Montepulciano (56)
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  • Monticiano (3)
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  • Pienza (40)
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  • Poggibonsi (29)
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  • Rapolano Terme (23)
  • San Casciano dei Bagni (7)
  • San Gimignano (76)
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  • Siena (184)
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  • Torrita di Siena (7)
  • Trequanda (5)
  • Vergelle (1)
  • Ville di Corsano (2)

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820 Holiday homes

Filters applied: Air conditioning (820)

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

1 / 21

Piancastagnaio ski home to rent.

Piancastagnaio / Casa del Corto

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay

from £79 / night

£547 / week

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from £79 / night

1 / 35

Castelnuovo Berardenga holiday home rental

Province of Siena / Castelnuovo Berardenga

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies

from £922 / night

£6448 - £7132 / week

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from £922 / night

1 / 42

Villa accommodation in Cetona with swimming pool

Province of Siena / Cetona

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay

from £340 / night

£2380 - £3875 / week

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from £340 / night

1 / 16

Asciano holiday farmhouse rental

Province of Siena / Asciano

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay

from £54 / night

£378 / week

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from £54 / night

1 / 25

Siena holiday villa rental

Province of Siena / Siena

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies

from £235 / night

£1641 - £2657 / week

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from £235 / night

1 / 23

Villa rental in Castelmuzio with swimming pool

Province of Siena / Castelmuzio

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min stay

from £392 / night

£2740 - £4590 / week

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from £392 / night

1 / 30

Villa rental in Cetona with swimming pool

Province of Siena / Cetona

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £205 / night

£1435 - £3719 / week

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from £205 / night

1 / 9

Holiday apartment with shared pool in Siena

Province of Siena / Siena

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £118 / night

£625 - £938 / week

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from £118 / night

1 / 100

Holiday villa with swimming pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies

from £922 / night

£6446 - £7133 / week

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from £922 / night

1 / 14

Holiday villa with swimming pool in Monteaperti

Castelnuovo Berardenga / Monteaperti

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay

from £107 / night

£743 - £1719 / week

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from £107 / night

1 / 11

Holiday apartment with shared pool in Poggibonsi

Province of Siena / Poggibonsi

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £90 / night

£625 - £750 / week

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from £90 / night

1 / 28

Holiday apartment in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from £55 / night

£383 - £547 / week

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from £55 / night

1 / 16

Contignano holiday villa rental

Radicofani / Contignano

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies

from £2813 / night

£11250 / week

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from £2813 / night

1 / 20

Holiday home in Isola d'Arbia

Siena / Isola d'Arbia

  • Sleeps 1
  • 7 nights min stay

from £89 / night

£617 - £1165 / week

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from £89 / night

1 / 13

Piancastagnaio ski home to rent.

Piancastagnaio / Casa del Corto

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay

from £110 / night

£766 / week

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from £110 / night

1 / 16

Contignano holiday villa rental

Radicofani / Contignano

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies

from £2813 / night

£11250 / week

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from £2813 / night

1 / 100

Holiday villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay

from £355 / night

£2483 - £3385 / week

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from £355 / night

1 / 101

Holiday apartment with shared pool in Bagno Vignoni

Province of Siena / Bagno Vignoni

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £63 / night

£383 - £547 / week

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from £63 / night

1 / 100

Villa rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay

from £391 / night

£2735 - £3125 / week

Enquire Enquire View

from £391 / night

(2) Very Good 

1 / 37

Holiday townhouse in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min stay

from £43 / night

£296 / week

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from £43 / night

1 / 20

Holiday villa in Castellina In Chianti

Province of Siena / Castellina In Chianti

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay

from £1028 / night

£7192 / week

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from £1028 / night

1 / 20

Holiday apartment in Casaglia

San Gimignano / Casaglia

  • 3 bedrooms
  • Sleeps 2
  • Min stay varies

from £129 / night

£773 - £1075 / week

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from £129 / night

1 / 100

Holiday apartment with shared pool in Bagno Vignoni

Province of Siena / Bagno Vignoni

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £63 / night

£383 - £547 / week

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from £63 / night

1 / 7

Apartment rental in Casole d'Elsa with shared pool

Province of Siena / Casole d'Elsa

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £67 / night

£430 - £735 / week

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from £67 / night

1 / 20

Holiday villa rental

Sovicille / Torri

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay

from £71 / night

£391 / week

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from £71 / night

1 / 24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay

from £679 / night

£4750 - £5795 / week

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from £679 / night

1 / 20

Holiday villa with swimming pool in Montepulicano

Pienza / Montepulicano

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies

from £235 / night

£1563 - £2930 / week

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from £235 / night

1 / 22

Holiday villa in Siena

Province of Siena / Siena

  • 5 bedrooms
  • Sleeps 13
  • 2 nights min stay

from £2317 / night

£7721 - £10295 / week

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from £2317 / night

1 / 20

Siena holiday villa accommodation

Province of Siena / Siena

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies

from £2014 / night

£14098 - £15701 / week

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from £2014 / night

1 / 18

Siena holiday villa rental

Province of Siena / Siena

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay

from £771 / night

£3204 - £5391 / week

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from £771 / night

1 / 10

Rapolano Terme holiday b&b rental

Province of Siena / Rapolano Terme

  • 1 bedroom
  • Sleeps 4
  • 5 nights min stay

from £94 / night

£508 - £836 / week

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from £94 / night

1 / 11

Holiday studio in Siena

Province of Siena / Siena

  • Studio
  • Sleeps 2
  • 7 nights min stay

from £56 / night

£391 / week

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from £56 / night

1 / 15

Holiday villa with shared pool in Radicondoli

Province of Siena / Radicondoli

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay

from £90 / night

£624 - £988 / week

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from £90 / night

1 / 26

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies

from £391 / night

£1485 - £2657 / week

Book Book View

from £391 / night

1 / 10

Holiday farmhouse with shared pool, golf nearby in Sinalunga

Province of Siena / Sinalunga

  • 5 bedrooms
  • Sleeps 10
  • 1 night min stay

from £235 / night

£1641 / week

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from £235 / night

(1) Excellent 

1 / 33

Holiday b&b in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

  • 5 bedrooms
  • Sleeps 11
  • 1 night min stay

from £51 / night

£329 - £1422 / week

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from £51 / night

1 / 21

Apartment rental in Poggibonsi with shared pool

Province of Siena / Poggibonsi

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £201 / night

£204 - £2344 / week

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from £201 / night

1 / 5

B&b rental in Rapolano Terme with shared pool

Province of Siena / Rapolano Terme

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay

from £79 / night

£547 / week

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from £79 / night

1 / 20

Holiday home in Asciano

Province of Siena / Asciano

  • Sleeps 1
  • 7 nights min stay

from £88 / night

£614 - £925 / week

Enquire Enquire View

from £88 / night

1 / 22

Apartment rental in Siena with shared pool

Province of Siena / Siena

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay

from £78 / night

£542 / week

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from £78 / night

1 / 24

Holiday apartment in Sant Andrea a Montecchio

Siena / Sant Andrea a Montecchio

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £83 / night

£500 - £629 / week

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from £83 / night

1 / 20

Holiday home accommodation

Province of Siena / Radicofani

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay

from £162 / night

£1133 - £2932 / week

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from £162 / night

1 / 4

Holiday villa with swimming pool in Rapolano Terme

Province of Siena / Rapolano Terme

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £168 / night

£1172 / week

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from £168 / night

1 / 20

Holiday home in Asciano

Province of Siena / Asciano

  • Sleeps 1
  • 7 nights min stay

from £75 / night

£521 - £795 / week

Enquire Enquire View

from £75 / night

1 / 5

Holiday b&b in Rapolano Terme

Province of Siena / Rapolano Terme

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from £43 / night

£219 - £313 / week

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from £43 / night

1 / 21

Villa rental in Chiusi with shared pool

Province of Siena / Chiusi

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £62 / night

£430 - £821 / week

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from £62 / night

1 / 32

Holiday villa rental

Province of Siena / Trequanda

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £252 / night

£1758 - £3118 / week

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from £252 / night

(12) Excellent 

1 / 23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min stay

from £165 / night

£1000 - £1500 / week

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from £165 / night

1 / 11

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay

from £63 / night

£407 / week

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from £63 / night

1 / 9

Holiday farmhouse with shared pool in Siena

Province of Siena / Siena

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from £102 / night

£508 / week

Book Book View

from £102 / night

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