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

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  • Province of Siena

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  • Chiusdino (31)
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  • Colle di Val d'Elsa (191)
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  • Trequanda (17)
  • Vergelle (7)
  • Ville di Corsano (11)
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  • Volte Basse (1)

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3,817 Holiday homes

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

(1) Excellent 

1 / 37

Holiday farmhouse with shared pool in Val d'Orcia

Montalcino / Val d'Orcia

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from $201 / night

$1405 - $1912 / week

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from $201 / night

1 / 100

Holiday apartment with shared pool in Siena

Province of Siena / Siena

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $145 / night

$1004 - $1784 / week

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from $145 / night

(2) Excellent 

1 / 22

Farmhouse letting in Radda in Chianti

Province of Siena / Radda in Chianti

2 bedroomsSleeps 3Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies

from $67 / night

$446 - $502 / week

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from $67 / night

Featured properties

1 / 20

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $125 / night

$870 - $1360 / week

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from $125 / night

1 / 8

Radicondoli holiday farmhouse rental

Province of Siena / Radicondoli

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $123 / night

$703 - $1282 / week

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from $123 / night

(1) Excellent 

1 / 20

Caprera holiday apartment rental

Siena / Caprera

1 bedroomSleeps 25 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 5 nights min stay

from $101 / night

$502 / week

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from $101 / night

1 / 15

Holiday villa in Valiano

Montepulciano / Valiano

5 bedroomsSleeps 97 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay

from $367 / night

$2569 - $5024 / week

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from $367 / night

1 / 21

Holiday villa in San Quirico d'Orcia

Province of Siena / San Quirico d'Orcia

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay

from $1478 / night

$10345 - $13528 / week

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from $1478 / night

1 / 34

Holiday villa with shared pool in Castel San Gimignano

San Gimignano / Castel San Gimignano

1 bedroomSleeps 57 nights min stay

  • 1 bedroom
  • Sleeps 5
  • 7 nights min stay

from $77 / night

$535 - $758 / week

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from $77 / night

1 / 100

Villa accommodation in San Gimignano with swimming pool

Province of Siena / San Gimignano

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $168 / night

$1115 - $2564 / week

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from $168 / night

(6) Very Good 

1 / 24

Villa letting in Poggibonsi with swimming pool

Province of Siena / Poggibonsi

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $263 / night

$1839 - $3065 / week

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from $263 / night

1 / 39

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay

from $637 / night

$4459 - $5796 / week

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from $637 / night

1 / 24

Villa rental in San Giovanni d'Asso with swimming pool

Province of Siena / San Giovanni d'Asso

8 bedroomsSleeps 167 nights min stay

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay

from $923 / night

$6461 - $8140 / week

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from $923 / night

1 / 39

Siena holiday villa rental

Province of Siena / Siena

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay

from $103 / night

$718 - $1444 / week

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from $103 / night

1 / 44

Montalcino holiday home rental

Province of Siena / Montalcino

12 bedroomsSleeps 267 nights min stay

  • 12 bedrooms
  • Sleeps 26
  • 7 nights min stay

from $797 / night

$5573 - $6810 / week

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from $797 / night

1 / 20

Villa rental in Val d'Orcia with swimming pool

Montalcino / Val d'Orcia

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $430 / night

$3004 - $5735 / week

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from $430 / night

1 / 17

Holiday apartment in Torrita di Siena

Province of Siena / Torrita di Siena

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay

from $179 / night

$1104 / week

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from $179 / night

1 / 20

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $253 / night

$1486 - $2077 / week

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from $253 / night

1 / 18

Ulignano holiday finca rental

San Gimignano / Ulignano

2 bedroomsSleeps 45 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min stay

from $145 / night

$992 / week

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from $145 / night

1 / 13

Holiday home in Torrita di Siena

Province of Siena / Torrita di Siena

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $67 / night

$469 - $758 / week

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from $67 / night

(1) Excellent 

1 / 100

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

6 bedroomsSleeps 12Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies

from $948 / night

$6019 - $8694 / week

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from $948 / night

1 / 21

Holiday farmhouse in Isola d'Arbia

Siena / Isola d'Arbia

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $86 / night

$601 - $1569 / week

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from $86 / night

1 / 25

Holiday villa with swimming pool in Sinalunga

Province of Siena / Sinalunga

8 bedroomsSleeps 167 nights min stay

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay

from $319 / night

$2230 - $4347 / week

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from $319 / night

1 / 23

Holiday apartment with shared pool in Asciano

Province of Siena / Asciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $151 / night

$574 - $1160 / week

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from $151 / night

1 / 24

Villa rental in Montalcino

Province of Siena / Montalcino

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from $1338 / night

$9362 / week

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from $1338 / night

1 / 12

Abbadia di Montepulciano holiday b&b rental

Montepulciano / Abbadia di Montepulciano

3 bedroomsSleeps 71 night min stay

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay

from $67 / night

$335 / week

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from $67 / night

(3) Good 

1 / 7

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

1 bedroomSleeps 51 night min stay

  • 1 bedroom
  • Sleeps 5
  • 1 night min stay

from $13 / night

$86 / week

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from $13 / night

1 / 15

Holiday farmhouse with shared pool in Larniano

San Gimignano / Larniano

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $282 / night

$1652 - $2634 / week

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from $282 / night

(1) Good 

1 / 10

Apartment rental in Colle di Val d'Elsa with shared pool

Colle di Val d'Elsa / Campiglia dei Foci

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay

from $67 / night

$424 / week

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from $67 / night

(1) Excellent 

1 / 45

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $244 / night

$1706 - $3712 / week

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from $244 / night

1 / 19

Holiday farmhouse accommodation

Province of Siena / Poggibonsi

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay

from $146 / night

$1025 - $1339 / week

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from $146 / night

1 / 19

Villa rental in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay

from $469 / night

$1672 / week

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from $469 / night

1 / 18

Sarteano holiday villa rental

Province of Siena / Sarteano

7 bedroomsSleeps 157 nights min stay

  • 7 bedrooms
  • Sleeps 15
  • 7 nights min stay

from $349 / night

$2441 - $5863 / week

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from $349 / night

1 / 14

Holiday apartment rental

Province of Siena / Siena

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $143 / night

$999 - $1335 / week

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from $143 / night

1 / 24

San Gimignano holiday cottage rental

Province of Siena / San Gimignano

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $160 / night

$1115 - $2842 / week

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from $160 / night

1 / 29

Holiday home rental

Sovicille / San Rocco a Pilli

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $120 / night

$836 - $1728 / week

Enquire Enquire View

from $120 / night

1 / 15

Asciano holiday apartment rental

Province of Siena / Asciano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $121 / night

$725 - $948 / week

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from $121 / night

1 / 45

Holiday villa with swimming pool in Siena

Province of Siena / Siena

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $271 / night

$1895 - $3712 / week

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from $271 / night

1 / 28

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $399 / night

$2787 - $5417 / week

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from $399 / night

(5) Very Good 

1 / 21

Holiday villa in Siena

Province of Siena / Siena

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay

from $558 / night

$3901 - $5446 / week

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from $558 / night

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