Holiday rentals in Province of Siena: Villas, Cottages and Apartments

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Bedrooms

Bathrooms

Location

  • Italy
  • Tuscany
  • Province of Siena

Location

  • All locations
  • Asciano (4)
  • Buonconvento (1)
  • Casole d'Elsa (15)
  • Castellina In Chianti (15)
  • Castelmuzio (1)
  • Castelnuovo Berardenga (11)
  • Castiglione D'Orcia (3)
  • Cetona (1)
  • Chianciano Terme (6)
  • Chiusdino (3)
  • Chiusi (1)
  • Colle di Val d'Elsa (8)
  • Gaiole in Chianti (18)
  • La Piazza (1)
  • Montalcino (5)
  • Montepulciano (11)
  • Monteriggioni (8)
  • Monteroni d'Arbia (3)
  • Monticiano (1)
  • Montisi (1)
  • Murlo (5)
  • Orgia (4)
  • Piancastagnaio (6)
  • Pienza (5)
  • Pievescola (1)
  • Poggibonsi (9)
  • Radda in Chianti (3)
  • Radicofani (4)
  • Radicondoli (6)
  • Rapolano Terme (3)
  • San Casciano dei Bagni (6)
  • San Gimignano (56)
  • San Giovanni d'Asso (5)
  • San Lorenzo a Merse (1)
  • Sarteano (4)
  • Siena (10)
  • Sinalunga (8)
  • Sovicille (4)
  • Torre A Castello (1)
  • Torrita di Siena (2)
  • Trequanda (2)
  • Vivo d'Orcia (1)

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263 Holiday homes

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

1 / 19

Montalcino holiday home rental

Province of Siena / Montalcino

2 6 2 nights min stay

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

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from £266 / night

£1858 / week

Book

from £266 / night

1 / 22

Holiday home in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

House / 1 bedroom / sleeps 4 / Min stay varies

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from £83 / night

£577 - £754 / week

Book

from £83 / night

1 / 23

Holiday home with swimming pool in Pienza

Province of Siena / Pienza

1 3 5 nights min stay

House / 1 bedroom / sleeps 3 / 5 nights min stay

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from £62 / night

£431 / week

Book

from £62 / night

Featured properties

(6) Excellent 

1 / 26

Holiday home in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min stay

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

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from £62 / night

£377 - £485 / week

Book

from £62 / night

(6) Very Good 

1 / 45

Montepulciano holiday home rental

Province of Siena / Montepulciano

3 5 Min stay varies

House / 3 bedrooms / sleeps 5 / Min stay varies

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from £66 / night

£385 - £462 / week

Book

from £66 / night

1 / 16

Holiday home with shared pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

3 8 Min stay varies

House / 3 bedrooms / sleeps 8 / Min stay varies

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from £57 / night

£331 - £554 / week

Book

from £57 / night

1 / 22

Holiday home with swimming pool in Castelmuzio

Province of Siena / Castelmuzio

5 10 7 nights min stay

House / 5 bedrooms / sleeps 10 / 7 nights min stay

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from £440 / night

£3077 / week

Book

from £440 / night

(39) Excellent 

1 / 22

Holiday home with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

House / 2 bedrooms / sleeps 4 / Min stay varies

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from £85 / night

£600 - £925 / week

Book

from £85 / night

1 / 17

Holiday home with shared pool in Poggibonsi

Province of Siena / Poggibonsi

2 4 1 night min stay

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

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from £39 / night

£270 - £539 / week

Book

from £39 / night

(1) Excellent 

1 / 27

Santa Maria, San Gimignano holiday home rental

San Gimignano / Santa Maria, San Gimignano

2 4 Min stay varies

House / 2 bedrooms / sleeps 4 / Min stay varies

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from £62 / night

£385 - £524 / week

Book

from £62 / night

1 / 10

Holiday home in Buonconvento

Province of Siena / Buonconvento

1 3 4 nights min stay

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

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from £50 / night

£347 - £500 / week

Book

from £50 / night

1 / 8

Monteriggioni holiday home rental

Province of Siena / Monteriggioni

4 8 3 nights min stay

House / 4 bedrooms / sleeps 8 / 3 nights min stay

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from £277 / night

£1924 / week

Book

from £277 / night

(3) Very Good 

1 / 15

Siena holiday home rental

Province of Siena / Siena

1 3 3 nights min stay

House / 1 bedroom / sleeps 3 / 3 nights min stay

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from £58 / night

£385 / week

Book

from £58 / night

(7) Excellent 

1 / 6

Valiano holiday home rental

Montepulciano / Valiano

1 2 4 nights min stay

House / 1 bedroom / sleeps 2 / 4 nights min stay

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from £39 / night

£270 / week

Book

from £39 / night

1 / 35

Holiday home in Murlo

Province of Siena / Murlo

3 6 2 nights min stay

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

Add to shortlist

from £170 / night

£1077 / week

Book

from £170 / night

1 / 21

Holiday home with shared pool in Vagliagli

Castelnuovo Berardenga / Vagliagli

1 3 3 nights min stay

House / 1 bedroom / sleeps 3 / 3 nights min stay

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from £58 / night

£404 - £647 / week

Book

from £58 / night

(3) Good 

1 / 5

Montepulciano holiday home rental

Province of Siena / Montepulciano

1 2 1 night min stay

House / 1 bedroom / sleeps 2 / 1 night min stay

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from £47 / night

£231 / week

Book

from £47 / night

(2) Very Good 

1 / 20

Home rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

4 5 Min stay varies

House / 4 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £94 / night

£624 - £1054 / week

Book

from £94 / night

1 / 39

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 6 7 nights min stay

House / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £103 / night

£716 - £1066 / week

Book

from £103 / night

(3) Very Good 

1 / 27

Gaiole in Chianti holiday home accommodation

Gaiole in Chianti / Montefienali

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

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from £40 / night

£240 - £424 / week

Book

from £40 / night

1 / 25

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

1 2 7 nights min stay

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

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from £60 / night

£416 - £485 / week

Book

from £60 / night

1 / 10

Holiday home with shared pool in Monteriggioni

Province of Siena / Monteriggioni

2 4 3 nights min stay

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

Add to shortlist

from £135 / night

£924 / week

Book

from £135 / night

1 / 24

Rapolano Terme holiday home rental

Province of Siena / Rapolano Terme

4 6 1 night min stay

House / 4 bedrooms / sleeps 6 / 1 night min stay

Add to shortlist

from £139 / night

£924 / week

Book

from £139 / night

(1) Excellent 

1 / 18

Holiday home rental

Province of Siena / Montisi

3 6 4 nights min stay

House / 3 bedrooms / sleeps 6 / 4 nights min stay

Add to shortlist

from £90 / night

£622 / week

Book

from £90 / night

1 / 54

Holiday home in Torre A Castello

Province of Siena / Torre A Castello

2 6 3 nights min stay

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

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from £54 / night

£385 - £500 / week

Book

from £54 / night

1 / 20

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

2 4 7 nights min stay

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

Add to shortlist

from £75 / night

£524 - £593 / week

Book

from £75 / night

1 / 6

Holiday home with shared pool in Montepulciano

Province of Siena / Montepulciano

1 3 1 night min stay

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

Add to shortlist

from £100 / night

£693 / week

Book

from £100 / night

(2) Very Good 

1 / 34

Holiday home with shared pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 4 Min stay varies

House / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £77 / night

£539 / week

Book

from £77 / night

1 / 22

Home letting in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 Min stay varies

House / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £116 / night

£462 - £539 / week

Book

from £116 / night

1 / 5

San Gimignano holiday home accommodation

Province of Siena / San Gimignano

1 4 1 night min stay

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

Add to shortlist

from £147 / night

£974 / week

Book

from £147 / night

1 / 23

Holiday home in Radicondoli

Province of Siena / Radicondoli

3 9 7 nights min stay

House / 3 bedrooms / sleeps 9 / 7 nights min stay

Add to shortlist

from £275 / night

£1924 / week

Book

from £275 / night

1 / 23

Home letting in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

1 3 Min stay varies

House / 1 bedroom / sleeps 3 / Min stay varies

Add to shortlist

from £70 / night

£616 / week

Book

from £70 / night

1 / 101

Holiday home with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

5 12 7 nights min stay

House / 5 bedrooms / sleeps 12 / 7 nights min stay

Add to shortlist

from £431 / night

£3011 - £3817 / week

Book

from £431 / night

(1) Very Good 

1 / 14

Pienza holiday home rental

Province of Siena / Pienza

2 4 2 nights min stay

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

Add to shortlist

from £116 / night

£531 / week

Book

from £116 / night

1 / 100

Holiday home in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

4 12 Min stay varies

House / 4 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £163 / night

£1135 - £2255 / week

Book

from £163 / night

1 / 20

Gaiole in Chianti holiday home accommodation

Province of Siena / Gaiole in Chianti

3 5 4 nights min stay

House / 3 bedrooms / sleeps 5 / 4 nights min stay

Add to shortlist

from £93 / night

£554 / week

Book

from £93 / night

(2) Excellent 

1 / 22

Montalcino holiday home rental

Province of Siena / Montalcino

2 5 1 night min stay

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

Add to shortlist

from £66 / night

£347 - £831 / week

Book

from £66 / night

1 / 14

Holiday home in Chiusdino

Province of Siena / Chiusdino

1 6 1 night min stay

House / 1 bedroom / sleeps 6 / 1 night min stay

Add to shortlist

from £54 / night

£324 / week

Book

from £54 / night

1 / 10

Holiday home rental

Province of Siena / Montalcino

1 6 2 nights min stay

House / 1 bedroom / sleeps 6 / 2 nights min stay

Add to shortlist

from £85 / night

£462 / week

Book

from £85 / night

1 / 26

Holiday home in Murlo

Province of Siena / Murlo

3 6 2 nights min stay

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

Add to shortlist

from £124 / night

£770 / week

Book

from £124 / night

1 / 100

Holiday home in Chianciano Terme

Province of Siena / Chianciano Terme

4 8 Min stay varies

House / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £110 / night

£765 - £1314 / week

Book

from £110 / night

1 / 21

Holiday home with shared pool in Vagliagli

Castelnuovo Berardenga / Vagliagli

2 5 4 nights min stay

House / 2 bedrooms / sleeps 5 / 4 nights min stay

Add to shortlist

from £143 / night

£997 / week

Book

from £143 / night

1 / 16

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

2 5 1 night min stay

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

Add to shortlist

from £77 / night

£385 / week

Book

from £77 / night

(1) Very Good 

1 / 11

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

House / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £54 / night

£324 - £577 / week

Book

from £54 / night

1 / 99

Holiday home rental

Province of Siena / Montepulciano

2 4 Min stay varies

House / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £80 / night

£558 - £849 / week

Book

from £80 / night

(2) Excellent 

1 / 9

Holiday home rental

Province of Siena / Montalcino

3 8 2 nights min stay

House / 3 bedrooms / sleeps 8 / 2 nights min stay

Add to shortlist

from £77 / night

£462 / week

Book

from £77 / night

1 / 54

Holiday home with shared pool in Sarteano

Province of Siena / Sarteano

2 4 Min stay varies

House / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £63 / night

£435 - £894 / week

Book

from £63 / night

1 / 13

Piancastagnaio ski home to rent.

Piancastagnaio / Casa del Corto

3 8 2 nights min stay

House / 3 bedrooms / sleeps 8 / 2 nights min stay

Add to shortlist

from £108 / night

£754 / week

Book

from £108 / night

1 / 100

Holiday home in Monticiano

Province of Siena / Monticiano

3 5 7 nights min stay

House / 3 bedrooms / sleeps 5 / 7 nights min stay

Add to shortlist

from £63 / night

£435 - £647 / week

Book

from £63 / night

1 / 100

Holiday home with swimming pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

5 12 5 nights min stay

House / 5 bedrooms / sleeps 12 / 5 nights min stay

Add to shortlist

from £138 / night

£961 - £1566 / week

Book

from £138 / night

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