Air conditioned apartments and villas to rent in Province of Siena

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  • Province of Siena

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  • Asciano (17)
  • Bagno Vignoni (11)
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  • Cetona (8)
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  • Chiusi (8)
  • Colle di Val d'Elsa (17)
  • Gaiole in Chianti (52)
  • Le Piazze (2)
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  • Montisi (6)
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  • Pienza (35)
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  • Poggibonsi (29)
  • Radda in Chianti (3)
  • Radicofani (11)
  • Radicondoli (2)
  • Rapolano Terme (23)
  • San Casciano dei Bagni (6)
  • San Gimignano (75)
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  • Siena (177)
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  • Torrita di Siena (7)
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  • Ville di Corsano (1)

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804 Holiday homes

Filters applied: Air conditioning (804)

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

(1) Very Good 

1 / 13

Montisi holiday villa rental

Province of Siena / Montisi

5 bedroomsSleeps 6Min stay varies

  • 5 bedrooms
  • Sleeps 6
  • Min stay varies

from $57 / night

$674 - $1515 / week

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from $57 / night

1 / 28

Holiday villa rental

Province of Siena / San Quirico d'Orcia

8 bedroomsSleeps 197 nights min stay

  • 8 bedrooms
  • Sleeps 19
  • 7 nights min stay

from $1853 / night

$12969 - $24916 / week

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from $1853 / night

1 / 5

Siena holiday finca rental

Province of Siena / Siena

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from $180 / night

$0 / week

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from $180 / night

Featured properties

1 / 35

Chiusdino holiday villa rental

Province of Siena / Chiusdino

16 bedroomsSleeps 423 nights min stay

  • 16 bedrooms
  • Sleeps 42
  • 3 nights min stay

from $24968 / night

$174773 - $180013 / week

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from $24968 / night

1 / 22

Holiday apartment with shared pool in Asciano

Province of Siena / Asciano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $158 / night

$1100 - $1383 / week

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from $158 / night

1 / 11

Holiday studio in Siena

Province of Siena / Siena

StudioSleeps 27 nights min stay

  • Studio
  • Sleeps 2
  • 7 nights min stay

from $81 / night

$562 / week

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from $81 / night

1 / 18

Holiday villa with swimming pool in Siena

Province of Siena / Siena

1 bedroomSleeps 7Min stay varies

  • 1 bedroom
  • Sleeps 7
  • Min stay varies

from $267 / night

$1863 - $2638 / week

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from $267 / night

1 / 17

San Gimignano holiday b&b rental

Province of Siena / San Gimignano

1 bedroomSleeps 25 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 5 nights min stay

from $101 / night

$663 / week

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from $101 / night

1 / 42

Holiday home in Pienza

Province of Siena / Pienza

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies

from $1659 / night

$11612 / week

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from $1659 / night

1 / 29

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 bedroomsSleeps 91 night min stay

  • 5 bedrooms
  • Sleeps 9
  • 1 night min stay

from $1123 / night

$7855 / week

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from $1123 / night

(7) Excellent 

1 / 34

Poggibonsi holiday villa accommodation

Province of Siena / Poggibonsi

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay

from $841 / night

$5881 - $7842 / week

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from $841 / night

1 / 20

Villa rental in Castiglione D'Orcia with swimming pool

Province of Siena / Castiglione D'Orcia

1 bedroomSleeps 217 nights min stay

  • 1 bedroom
  • Sleeps 21
  • 7 nights min stay

from $590 / night

$4130 - $6397 / week

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from $590 / night

1 / 15

Holiday home with shared pool in San Lorenzo a Merse

Province of Siena / San Lorenzo a Merse

14 bedroomsSleeps 287 nights min stay

  • 14 bedrooms
  • Sleeps 28
  • 7 nights min stay

from $4762 / night

$33329 / week

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from $4762 / night

1 / 30

Ville di Corsano holiday villa rental

Province of Siena / Ville di Corsano

9 bedroomsSleeps 187 nights min stay

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min stay

from $2052 / night

$14364 - $21602 / week

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from $2052 / night

1 / 7

Apartment rental in Casole d'Elsa with shared pool

Province of Siena / Casole d'Elsa

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $96 / night

$618 - $1055 / week

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from $96 / night

1 / 12

Montepulciano holiday cottage let

Province of Siena / Montepulciano

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay

from $140 / night

$975 / week

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from $140 / night

1 / 52

Holiday home in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies

from $1499 / night

$10492 / week

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from $1499 / night

1 / 24

Holiday apartment in Sant Andrea a Montecchio

Siena / Sant Andrea a Montecchio

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $118 / night

$719 - $904 / week

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from $118 / night

1 / 25

Castelnuovo Berardenga holiday apartment rental

Province of Siena / Castelnuovo Berardenga

2 bedroomsSleeps 7Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies

from $101 / night

$707 - $1271 / week

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from $101 / night

1 / 16

Holiday home in Montalcino

Province of Siena / Montalcino

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies

from $1421 / night

$9943 / week

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from $1421 / night

1 / 26

Holiday villa with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

12 bedroomsSleeps 247 nights min stay

  • 12 bedrooms
  • Sleeps 24
  • 7 nights min stay

from $574 / night

$4018 - $8832 / week

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from $574 / night

1 / 15

Holiday villa rental

San Gimignano / Ulignano

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay

from $705 / night

$4932 - $6958 / week

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from $705 / night

1 / 55

Holiday farmhouse in Cetona

Province of Siena / Cetona

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $135 / night

$730 - $842 / week

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from $135 / night

1 / 18

Rapolano Terme holiday b&b rental

Province of Siena / Rapolano Terme

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies

from $87 / night

$0 / week

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from $87 / night

1 / 24

Holiday home with swimming pool in Pienza

Province of Siena / Pienza

1 bedroomSleeps 35 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 5 nights min stay

from $141 / night

$0 / week

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from $141 / night

1 / 28

Holiday villa in Radicofani

Province of Siena / Radicofani

5 bedroomsSleeps 117 nights min stay

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min stay

from $236 / night

$1650 - $3704 / week

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from $236 / night

1 / 19

Holiday b&b rental

San Gimignano / Ulignano

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from $90 / night

$0 / week

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from $90 / night

(3) Excellent 

1 / 49

San Giovanni d'Asso holiday apartment rental

Province of Siena / San Giovanni d'Asso

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $270 / night

$1768 - $1936 / week

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from $270 / night

(10) Excellent 

1 / 21

Gracciano holiday cottage rental

Montepulciano / Gracciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $90 / night

$517 - $2312 / week

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from $90 / night

1 / 16

Holiday b&b rental

Gaiole in Chianti / Lecchi

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay

from $124 / night

$674 / week

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from $124 / night

1 / 20

Holiday farmhouse rental

Province of Siena / Pienza

6 bedroomsSleeps 137 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay

from $462 / night

$3232 - $7721 / week

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from $462 / night

1 / 25

Siena holiday villa rental

Province of Siena / Siena

5 bedroomsSleeps 127 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay

from $236 / night

$1650 - $3816 / week

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from $236 / night

1 / 11

Holiday apartment with shared pool in Chianciano Terme

Province of Siena / Chianciano Terme

1 bedroomSleeps 37 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay

from $101 / night

$0 / week

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from $101 / night

1 / 20

Holiday villa with swimming pool in Montalcino

Province of Siena / Montalcino

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay

from $1741 / night

$12184 - $13466 / week

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from $1741 / night

1 / 20

Siena holiday villa accommodation

Province of Siena / Siena

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies

from $2961 / night

$20725 - $23081 / week

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from $2961 / night

1 / 35

Castelnuovo Berardenga holiday home rental

Province of Siena / Castelnuovo Berardenga

9 bedroomsSleeps 18Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies

from $1323 / night

$9261 - $10243 / week

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from $1323 / night

1 / 22

Montepulciano holiday villa rental

Province of Siena / Montepulciano

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay

from $337 / night

$2357 / week

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from $337 / night

1 / 22

Chiusi holiday villa accommodation

Province of Siena / Chiusi

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies

from $320 / night

$2245 - $5050 / week

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from $320 / night

1 / 18

Holiday villa in Castelnuovo Dell'abate

Province of Siena / Castelnuovo Dell'abate

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $393 / night

$2189 - $3647 / week

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from $393 / night

1 / 6

Siena holiday farmhouse rental

Province of Siena / Siena

1 bedroomSleeps 32 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay

from $146 / night

$674 / week

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from $146 / night

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