Air conditioned apartments and villas to rent in Province of Siena

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  • Italy
  • Tuscany
  • Province of Siena

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  • Asciano (20)
  • Bagno Vignoni (11)
  • Buonconvento (13)
  • Casciano (1)
  • Casole d'Elsa (9)
  • Castellina In Chianti (14)
  • Castelmuzio (2)
  • Castelnuovo Berardenga (36)
  • Castiglione D'Orcia (4)
  • Cetona (8)
  • Chianciano Terme (4)
  • Chiusdino (2)
  • Chiusi (7)
  • Colle di Val d'Elsa (15)
  • Gaiole in Chianti (52)
  • Le Piazze (2)
  • Montalcino (43)
  • Montecchio (1)
  • Montepulciano (51)
  • Monteriggioni (14)
  • Monteroni d'Arbia (15)
  • Monticiano (3)
  • Montisi (7)
  • Murlo (8)
  • Piancastagnaio (6)
  • Pienza (40)
  • Pievescola (1)
  • Poggibonsi (28)
  • Radda in Chianti (4)
  • Radicofani (8)
  • Radicondoli (1)
  • Rapolano Terme (22)
  • San Casciano dei Bagni (6)
  • San Gimignano (70)
  • San Giovanni d'Asso (22)
  • San Lorenzo a Merse (1)
  • San Quirico d'Orcia (2)
  • Sarteano (4)
  • Siena (176)
  • Sinalunga (14)
  • Sovicille (9)
  • Torrita di Siena (7)
  • Trequanda (5)
  • Ville di Corsano (2)

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772 Holiday homes

Filters applied: Air conditioning (772)

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

(3) Excellent 

1 / 49

San Giovanni d'Asso holiday apartment rental

Province of Siena / San Giovanni d'Asso

3 6 2 nights min stay

Apartment / 3 bedrooms / sleeps 6 / 2 nights min stay

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from £184 / night

£1203 - £1317 / week

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from £184 / night

(5) Excellent 

1 / 19

Holiday farmhouse with swimming pool in San Fabiano

Monteroni d'Arbia / San Fabiano

6 20 Min stay varies

Farmhouse / 6 bedrooms / sleeps 20 / Min stay varies

Add to shortlist

from £561 / night

£3258 - £4394 / week

Book

from £561 / night

(1) Very Good 

1 / 29

Holiday apartment in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

2 4 2 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 2 nights min stay

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from £133 / night

£853 - £929 / week

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from £133 / night

Featured properties

1 / 24

Holiday apartment with indoor pool in Pienza

Province of Siena / Pienza

8 15 7 nights min stay

Apartment / 8 bedrooms / sleeps 15 / 7 nights min stay

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from £433 / night

£3031 - £5811 / week

Book

from £433 / night

1 / 9

Casole d'Elsa holiday apartment let

Province of Siena / Casole d'Elsa

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £69 / night

£455 - £788 / week

Book

from £69 / night

1 / 13

Holiday apartment in Siena

Province of Siena / Siena

1 4 Min stay varies

Apartment / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £151 / night

£1055 / week

Book

from £151 / night

(6) Excellent 

1 / 64

Holiday lodge in Pienza

Province of Siena / Pienza

3 8 7 nights min stay

Lodge / 3 bedrooms / sleeps 8 / 7 nights min stay

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from £177 / night

£1237 - £2252 / week

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from £177 / night

(1) Excellent 

1 / 20

Caprera holiday apartment rental

Siena / Caprera

1 2 5 nights min stay

Apartment / 1 bedroom / sleeps 2 / 5 nights min stay

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from £49 / night

£304 - £341 / week

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from £49 / night

1 / 7

Apartment rental in Casole d'Elsa with shared pool

Province of Siena / Casole d'Elsa

1 4 Min stay varies

Apartment / 1 bedroom / sleeps 4 / Min stay varies

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from £65 / night

£417 - £713 / week

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from £65 / night

1 / 13

Siena holiday apartment rental

Province of Siena / Siena

2 5 Min stay varies

Apartment / 2 bedrooms / sleeps 5 / Min stay varies

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from £137 / night

£959 / week

Book

from £137 / night

1 / 19

Holiday apartment in Casaglia

San Gimignano / Casaglia

2 2 Min stay varies

Apartment / 2 bedrooms / sleeps 2 / Min stay varies

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from £113 / night

£729 - £1001 / week

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from £113 / night

(1) Very Good 

1 / 30

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

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from £107 / night

£642 - £1031 / week

Book

from £107 / night

1 / 18

Holiday apartment in Siena

Province of Siena / Siena

1 2 7 nights min stay

Apartment / 1 bedroom / sleeps 2 / 7 nights min stay

Add to shortlist

from £137 / night

£959 / week

Book

from £137 / night

1 / 24

Holiday apartment in Siena

Province of Siena / Siena

2 5 Min stay varies

Apartment / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £411 / night

£2877 / week

Book

from £411 / night

1 / 30

Holiday apartment with shared pool in Sinalunga

Province of Siena / Sinalunga

1 2 Min stay varies

Apartment / 1 bedroom / sleeps 2 / Min stay varies

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from £84 / night

£443 - £611 / week

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from £84 / night

1 / 48

Fort letting in Montisi with shared pool

Province of Siena / Montisi

1 3 4 nights min stay

Fort / 1 bedroom / sleeps 3 / 4 nights min stay

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from £94 / night

£650 - £722 / week

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from £94 / night

1 / 28

Siena holiday b&b rental

Province of Siena / Siena

1 2 1 night min stay

B&B / 1 bedroom / sleeps 2 / 1 night min stay

Add to shortlist

from £65 / night

£428 / week

Book

from £65 / night

1 / 12

Cedda holiday apartment rental

Poggibonsi / Cedda

2 4 7 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 7 nights min stay

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from £65 / night

£449 - £561 / week

Book

from £65 / night

1 / 11

Cedda holiday apartment rental

Poggibonsi / Cedda

2 4 7 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 7 nights min stay

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from £65 / night

£449 - £561 / week

Book

from £65 / night

1 / 25

Pienza holiday lodge rental

Province of Siena / Pienza

1 2 7 nights min stay

Lodge / 1 bedroom / sleeps 2 / 7 nights min stay

Add to shortlist

from £58 / night

£402 - £644 / week

Book

from £58 / night

1 / 4

Holiday apartment with swimming pool in San Fabiano

Monteroni d'Arbia / San Fabiano

2 5 Min stay varies

Apartment / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £114 / night

£607 - £910 / week

Book

from £114 / night

1 / 9

Holiday farmhouse in Siena

Province of Siena / Siena

2 4 2 nights min stay

Farmhouse / 2 bedrooms / sleeps 4 / 2 nights min stay

Add to shortlist

from £91 / night

£379 / week

Book

from £91 / night

1 / 4

Holiday apartment with swimming pool in San Fabiano

Monteroni d'Arbia / San Fabiano

2 5 Min stay varies

Apartment / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £99 / night

£569 - £758 / week

Book

from £99 / night

(1) Excellent 

1 / 24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 10 7 nights min stay

Villa / 6 bedrooms / sleeps 10 / 7 nights min stay

Add to shortlist

from £191 / night

£1336 - £2825 / week

Book

from £191 / night

1 / 5

Holiday apartment with swimming pool in San Fabiano

Monteroni d'Arbia / San Fabiano

2 4 Min stay varies

Apartment / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £99 / night

£569 - £758 / week

Book

from £99 / night

1 / 22

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 5 Min stay varies

Apartment / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £88 / night

£611 - £802 / week

Book

from £88 / night

1 / 16

Asciano holiday farmhouse rental

Province of Siena / Asciano

1 2 7 nights min stay

Farmhouse / 1 bedroom / sleeps 2 / 7 nights min stay

Add to shortlist

from £53 / night

£366 / week

Book

from £53 / night

1 / 15

Holiday b&b in Poggibonsi

Province of Siena / Poggibonsi

1 2 1 night min stay

B&B / 1 bedroom / sleeps 2 / 1 night min stay

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from £35 / night

£239 / week

Book

from £35 / night

(1) Excellent 

1 / 36

Holiday farmhouse with shared pool in Acquaviva di Montepulciano

Montepulciano / Acquaviva di Montepulciano

2 6 Min stay varies

Farmhouse / 2 bedrooms / sleeps 6 / Min stay varies

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from £107 / night

£637 - £1023 / week

Book

from £107 / night

(1) Excellent 

1 / 16

Apartment rental in Siena

Province of Siena / Siena

2 4 3 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 3 nights min stay

Add to shortlist

from £191 / night

£1146 / week

Book

from £191 / night

1 / 14

Holiday home in Casole d'Elsa

Province of Siena / Casole d'Elsa

1 4 Min stay varies

House / 1 bedroom / sleeps 4 / Min stay varies

Add to shortlist

from £61 / night

£379 - £675 / week

Book

from £61 / night

1 / 22

Holiday apartment in Siena

Province of Siena / Siena

1 5 Min stay varies

Apartment / 1 bedroom / sleeps 5 / Min stay varies

Add to shortlist

from £69 / night

£478 / week

Book

from £69 / night

1 / 13

Holiday home rental

Province of Siena / Siena

2 5 Min stay varies

House / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £152 / night

£985 - £1364 / week

Book

from £152 / night

1 / 12

Holiday b&b rental

Montalcino / Val d'Orcia

1 2 2 nights min stay

B&B / 1 bedroom / sleeps 2 / 2 nights min stay

Add to shortlist

from £91 / night

£607 / week

Book

from £91 / night

1 / 19

Rapolano Terme holiday b&b rental

Province of Siena / Rapolano Terme

1 3 Min stay varies

B&B / 1 bedroom / sleeps 3 / Min stay varies

Add to shortlist

from £59 / night

£412 / week

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from £59 / night

1 / 10

Siena holiday apartment rental

Province of Siena / Siena

2 4 7 nights min stay

Apartment / 2 bedrooms / sleeps 4 / 7 nights min stay

Add to shortlist

from £138 / night

£993 / week

Book

from £138 / night

1 / 18

Apartment rental in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 5 1 night min stay

Apartment / 2 bedrooms / sleeps 5 / 1 night min stay

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from £46 / night

£298 - £405 / week

Book

from £46 / night

1 / 16

Holiday b&b accommodation

Province of Siena / Rapolano Terme

1 2 Min stay varies

B&B / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £38 / night

£262 / week

Book

from £38 / night

1 / 12

Holiday farmhouse with shared pool in Isola d'Arbia

Siena / Isola d'Arbia

2 6 Min stay varies

Farmhouse / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £52 / night

£359 - £978 / week

Book

from £52 / night

1 / 17

Rapolano Terme holiday b&b rental

Province of Siena / Rapolano Terme

1 2 Min stay varies

B&B / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £43 / night

£300 / week

Book

from £43 / night

1 / 18

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 2 nights min stay

Apartment / 1 bedroom / sleeps 3 / 2 nights min stay

Add to shortlist

from £61 / night

£306 / week

Book

from £61 / night

1 / 17

Holiday b&b in Rapolano Terme

Province of Siena / Rapolano Terme

1 2 Min stay varies

B&B / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £45 / night

£310 / week

Book

from £45 / night

1 / 10

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

3 5 1 night min stay

Apartment / 3 bedrooms / sleeps 5 / 1 night min stay

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from £77 / night

£344 / week

Book

from £77 / night

1 / 19

Holiday apartment rental

Province of Siena / Castelnuovo Berardenga

1 4 1 night min stay

Apartment / 1 bedroom / sleeps 4 / 1 night min stay

Add to shortlist

from £31 / night

£214 - £321 / week

Book

from £31 / night

1 / 15

Holiday apartment in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

1 4 1 night min stay

Apartment / 1 bedroom / sleeps 4 / 1 night min stay

Add to shortlist

from £31 / night

£214 - £321 / week

Book

from £31 / night

1 / 4

Piancastagnaio holiday home rental

Piancastagnaio / Casa del Corto

2 6 2 nights min stay

House / 2 bedrooms / sleeps 6 / 2 nights min stay

Add to shortlist

from £92 / night

£642 / week

Book

from £92 / night

(1) Excellent 

1 / 20

Holiday b&b letting

Province of Siena / Rapolano Terme

1 3 Min stay varies

B&B / 1 bedroom / sleeps 3 / Min stay varies

Add to shortlist

from £59 / night

£412 / week

Book

from £59 / night

1 / 17

Holiday apartment in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 4 1 night min stay

Apartment / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £31 / night

£214 - £321 / week

Book

from £31 / night

1 / 15

San Gimignano holiday farmhouse rental

Province of Siena / San Gimignano

2 4 Min stay varies

Farmhouse / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £45 / night

£298 - £464 / week

Book

from £45 / night

1 / 17

Apartment accommodation in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

1 3 1 night min stay

Apartment / 1 bedroom / sleeps 3 / 1 night min stay

Add to shortlist

from £31 / night

£214 - £268 / week

Book

from £31 / night

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