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  • Italy
  • Tuscany
  • Province of Siena

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  • Abbadia San Salvatore (2)
  • Asciano (36)
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  • Brenna (2)
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  • Campiglia d'Orcia (1)
  • Casole d'Elsa (63)
  • Castellina In Chianti (38)
  • Castelmuzio (4)
  • Castelnuovo Berardenga (58)
  • Castiglione D'Orcia (17)
  • Cetona (50)
  • Chianciano Terme (18)
  • Chiusdino (15)
  • Chiusi (11)
  • Colle di Val d'Elsa (22)
  • Gaiole in Chianti (55)
  • La Piazza (1)
  • Le Piazze (4)
  • Montalcino (36)
  • Montecchio (5)
  • Montepulciano (81)
  • Monteriggioni (31)
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  • Radda in Chianti (30)
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  • Rapolano Terme (19)
  • Rosia (5)
  • San Casciano dei Bagni (24)
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  • San Giovanni d'Asso (20)
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  • Strove (1)
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  • Torrita di Siena (14)
  • Trequanda (6)
  • Ville di Corsano (7)
  • Vivo d'Orcia (1)

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1,343 Holiday homes

Filters applied: Private garden (1,343)

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

1 / 24

Holiday villa in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

9 18 Min stay varies

Villa / 9 bedrooms / sleeps 18 / Min stay varies

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from £250 / night

£1531 - £2577 / week

Book

from £250 / night

(4) Excellent 

1 / 99

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

10 20 Min stay varies

Villa / 10 bedrooms / sleeps 20 / Min stay varies

Add to shortlist

from £608 / night

£2425 - £3681 / week

Book

from £608 / night

(5) Excellent 

1 / 56

Holiday guest house in Siena

Province of Siena / Siena

2 4 2 nights min stay

Guest house / 2 bedrooms / sleeps 4 / 2 nights min stay

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from £347 / night

£2116 / week

Book

from £347 / night

Featured properties

1 / 24

Montepulciano holiday villa rental

Province of Siena / Montepulciano

6 12 Min stay varies

Villa / 6 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £170 / night

£1885 - £3231 / week

Book

from £170 / night

1 / 16

Holiday b&b rental

Province of Siena / Montepulciano

4 8 1 night min stay

B&B / 4 bedrooms / sleeps 8 / 1 night min stay

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from £231 / night

£1385 / week

Book

from £231 / night

(15) Very Good 

1 / 97

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

7 16 1 night min stay

Farmhouse / 7 bedrooms / sleeps 16 / 1 night min stay

Add to shortlist

from £462 / night

£2693 / week

Book

from £462 / night

(1) Very Good 

1 / 35

Villa accommodation in San Gimignano with swimming pool

Province of Siena / San Gimignano

7 10 Min stay varies

Villa / 7 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £224 / night

£1462 - £2077 / week

Book

from £224 / night

1 / 23

Montalcino holiday farmhouse accommodation

Province of Siena / Montalcino

3 8 7 nights min stay

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

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from £200 / night

£1400 - £1885 / week

Book

from £200 / night

(1) Very Good 

1 / 12

Holiday villa letting

Province of Siena / Siena

7 14 3 nights min stay

Villa / 7 bedrooms / sleeps 14 / 3 nights min stay

Add to shortlist

from £354 / night

£2158 - £4297 / week

Book

from £354 / night

1 / 24

Holiday villa in Monteriggioni

Province of Siena / Monteriggioni

5 14 7 nights min stay

Villa / 5 bedrooms / sleeps 14 / 7 nights min stay

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from £231 / night

£1616 - £3939 / week

Book

from £231 / night

1 / 24

Holiday apartment in Val di Merse

Siena / Val di Merse

6 14 Min stay varies

Apartment / 6 bedrooms / sleeps 14 / Min stay varies

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from £231 / night

£1539 - £1847 / week

Book

from £231 / night

(9) Excellent 

1 / 31

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 £154 / night

£1097 - £1174 / week

Book

from £154 / night

1 / 14

Valiano holiday farmhouse let

Montepulciano / Valiano

11 22 2 nights min stay

Farmhouse / 11 bedrooms / sleeps 22 / 2 nights min stay

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from £654 / night

£4577 / week

Book

from £654 / night

(1) Very Good 

1 / 8

Holiday villa with swimming pool, golf nearby in Larniano

San Gimignano / Larniano

5 10 Min stay varies

Villa / 5 bedrooms / sleeps 10 / Min stay varies

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from £193 / night

£1347 - £1924 / week

Book

from £193 / night

1 / 25

Farmhouse rental in Gaiole in Chianti with swimming pool

Province of Siena / Gaiole in Chianti

6 12 3 nights min stay

Farmhouse / 6 bedrooms / sleeps 12 / 3 nights min stay

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from £300 / night

£2500 - £2800 / week

Book

from £300 / night

(3) Excellent 

1 / 22

Villa rental in Siena with swimming pool

Province of Siena / Siena

9 18 Min stay varies

Villa / 9 bedrooms / sleeps 18 / Min stay varies

Add to shortlist

from £347 / night

£1924 - £3385 / week

Book

from £347 / night

(1) Excellent 

1 / 29

Holiday farmhouse in Montepulciano

Province of Siena / Montepulciano

4 8 Min stay varies

Farmhouse / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £208 / night

£1154 - £1808 / week

Book

from £208 / night

1 / 18

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

7 14 7 nights min stay

Villa / 7 bedrooms / sleeps 14 / 7 nights min stay

Add to shortlist

from £330 / night

£2308 - £4616 / week

Book

from £330 / night

1 / 54

Cetona holiday farmhouse rental

Province of Siena / Cetona

8 12 2 nights min stay

Farmhouse / 8 bedrooms / sleeps 12 / 2 nights min stay

Add to shortlist

from £270 / night

£2000 / week

Book

from £270 / night

(14) Excellent 

1 / 16

Holiday apartment with shared pool in Buonconvento

Province of Siena / Buonconvento

4 8 7 nights min stay

Apartment / 4 bedrooms / sleeps 8 / 7 nights min stay

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from £179 / night

£1250 - £1710 / week

Book

from £179 / night

(1) Excellent 

1 / 13

Holiday villa with shared pool, golf nearby in Sovicille

Province of Siena / Sovicille

3 4 3 nights min stay

Villa / 3 bedrooms / sleeps 4 / 3 nights min stay

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from £270 / night

£1693 - £2693 / week

Book

from £270 / night

1 / 45

Holiday farmhouse in Radicofani

Province of Siena / Radicofani

6 16 Min stay varies

Farmhouse / 6 bedrooms / sleeps 16 / Min stay varies

Add to shortlist

from £58 / night

£1697 / week

Book

from £58 / night

1 / 22

Montepulciano holiday villa rental

Province of Siena / Montepulciano

5 10 7 nights min stay

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

Add to shortlist

from £231 / night

£1616 / week

Book

from £231 / night

1 / 39

Holiday villa in Sinalunga

Province of Siena / Sinalunga

3 7 Min stay varies

Villa / 3 bedrooms / sleeps 7 / Min stay varies

Add to shortlist

from £193 / night

£1347 - £1808 / week

Book

from £193 / night

1 / 24

Siena holiday villa rental

Province of Siena / Siena

4 9 7 nights min stay

Villa / 4 bedrooms / sleeps 9 / 7 nights min stay

Add to shortlist

from £331 / night

£2308 - £3847 / week

Book

from £331 / night

(26) Excellent 

1 / 25

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

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from £77 / night

£424 - £654 / week

Book

from £77 / night

(1) Excellent 

1 / 21

Cetona holiday farmhouse rental

Province of Siena / Cetona

4 7 1 night min stay

Farmhouse / 4 bedrooms / sleeps 7 / 1 night min stay

Add to shortlist

from £162 / night

£1131 / week

Book

from £162 / night

(2) Very Good 

1 / 21

Holiday townhouse rental

Province of Siena / San Gimignano

2 5 Min stay varies

Townhouse / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £97 / night

£562 - £854 / week

Book

from £97 / night

1 / 33

Holiday villa in Siena

Province of Siena / Siena

6 13 Min stay varies

Villa / 6 bedrooms / sleeps 13 / Min stay varies

Add to shortlist

from £215 / night

£1500 - £4077 / week

Book

from £215 / night

1 / 13

Holiday villa rental

Province of Siena / San Gimignano

5 10 Min stay varies

Villa / 5 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £154 / night

£893 - £2526 / week

Book

from £154 / night

(2) Excellent 

1 / 17

San Gimignano holiday villa accommodation

Province of Siena / San Gimignano

3 6 Min stay varies

Villa / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £85 / night

£600 - £900 / week

Book

from £85 / night

(41) Excellent 

1 / 18

Holiday villa letting

Province of Siena / Sinalunga

12 23 Min stay varies

Villa / 12 bedrooms / sleeps 23 / Min stay varies

Add to shortlist

from £306 / night

£2140 - £6339 / week

Book

from £306 / night

1 / 36

Holiday villa in Siena

Province of Siena / Siena

11 22 Min stay varies

Villa / 11 bedrooms / sleeps 22 / Min stay varies

Add to shortlist

from £462 / night

£2539 - £4231 / week

Book

from £462 / night

1 / 18

Holiday villa with swimming pool in Chiusi

Province of Siena / Chiusi

6 12 Min stay varies

Villa / 6 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £264 / night

£1385 - £2308 / week

Book

from £264 / night

(9) Excellent 

1 / 42

Holiday villa rental

Province of Siena / San Giovanni d'Asso

8 16 Min stay varies

Villa / 8 bedrooms / sleeps 16 / Min stay varies

Add to shortlist

from £487 / night

£3668 - £4616 / week

Book

from £487 / night

1 / 14

Montepulciano holiday watermill rental

Province of Siena / Montepulciano

6 10 Min stay varies

Watermill / 6 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £193 / night

£1454 / week

Book

from £193 / night

1 / 27

Villa rental in Siena with swimming pool

Province of Siena / Siena

4 10 Min stay varies

Villa / 4 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £215 / night

£1500 - £3962 / week

Book

from £215 / night

(2) Excellent 

1 / 10

Holiday townhouse with swimming pool in Sovicille

Province of Siena / Sovicille

2 5 2 nights min stay

Townhouse / 2 bedrooms / sleeps 5 / 2 nights min stay

Add to shortlist

from £35 / night

£377 - £1939 / week

Book

from £35 / night

(1) Very Good 

1 / 21

Montepulciano holiday farmhouse rental

Province of Siena / Montepulciano

3 6 5 nights min stay

Farmhouse / 3 bedrooms / sleeps 6 / 5 nights min stay

Add to shortlist

from £162 / night

£1077 / week

Book

from £162 / night

1 / 31

Villa letting in Siena with swimming pool

Province of Siena / Siena

3 7 Min stay varies

Villa / 3 bedrooms / sleeps 7 / Min stay varies

Add to shortlist

from £193 / night

£1347 - £1808 / week

Book

from £193 / night

(11) Very Good 

1 / 27

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 7 nights min stay

Villa / 3 bedrooms / sleeps 7 / 7 nights min stay

Add to shortlist

from £159 / night

£1108 - £1847 / week

Book

from £159 / night

(5) Very Good 

1 / 49

Montisi holiday fort rental

Province of Siena / Montisi

1 3 4 nights min stay

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

Add to shortlist

from £96 / night

£660 - £733 / week

Book

from £96 / night

1 / 22

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 Min stay varies

Villa / 5 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £231 / night

£1616 - £2077 / week

Book

from £231 / night

1 / 18

Holiday apartment with shared pool in Trequanda

Province of Siena / Trequanda

1 2 Min stay varies

Apartment / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £154 / night

£1072 - £1610 / week

Book

from £154 / night

1 / 12

Montepulciano holiday farmhouse rental

Province of Siena / Montepulciano

4 10 5 nights min stay

Farmhouse / 4 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £216 / night

£1308 / week

Book

from £216 / night

1 / 26

Holiday apartment with shared pool in Trequanda

Province of Siena / Trequanda

1 2 Min stay varies

Apartment / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £154 / night

£1072 - £1539 / week

Book

from £154 / night

1 / 24

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

6 12 3 nights min stay

Villa / 6 bedrooms / sleeps 12 / 3 nights min stay

Add to shortlist

from £993 / night

£6847 / week

Book

from £993 / night

(3) Excellent 

1 / 24

Holiday villa in Costalpino

Siena / Costalpino

3 6 3 nights min stay

Villa / 3 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £230 / night

£1538 - £1827 / week

Book

from £230 / night

1 / 45

Holiday villa with shared pool in Buonconvento

Province of Siena / Buonconvento

10 20 1 night min stay

Villa / 10 bedrooms / sleeps 20 / 1 night min stay

Add to shortlist

from £567 / night

£3964 / week

Book

from £567 / night

1 / 20

Holiday apartment in Casaglia

San Gimignano / Casaglia

3 2 Min stay varies

Apartment / 3 bedrooms / sleeps 2 / Min stay varies

Add to shortlist

from £127 / night

£761 - £1058 / week

Book

from £127 / night

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