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

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Province of Siena

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3,753 Holiday homes

12

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

9 20 7 nights min

  • 9 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £673 / night

£3446 / week

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from £673 / night

12

Province of Siena / Montalcino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

from £100 / night

£667 / week

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from £100 / night

21

Holiday apartment with shared pool in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £52 / night

£362 - £639 / week

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from £52 / night

10

Rapolano Terme holiday b&b rental

Province of Siena / Rapolano Terme

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £101 / night

£547 - £900 / week

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from £101 / night

23

Holiday farmhouse rental

Province of Siena / Castellina In Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

Pricing unknown

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Pricing unknown

4

Holiday farmhouse with shared pool, golf nearby in Monteriggioni

Province of Siena / Monteriggioni

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

Pricing unknown

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Pricing unknown

20

Province of Siena / Monteriggioni

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Air conditioning

from £37 / night

£253 / week

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from £37 / night

12

Holiday apartment with shared pool in Cedda

Poggibonsi / Cedda

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £61 / night

£421 / week

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from £61 / night

44

Montalcino holiday home rental

Province of Siena / Montalcino

12 26 7 nights min

  • 12 bedrooms
  • Sleeps 26
  • 7 nights min
  • Child friendly
  • Pet friendly

from £685 / night

£4790 - £4967 / week

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from £685 / night

(3) Average 

10

Province of Siena / Radicofani

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

Pricing unknown

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Pricing unknown

(1) Excellent 

27

Lodge rental in Pienza with shared pool

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £80 / night

£559 - £883 / week

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from £80 / night

(1) Excellent 

16

Holiday farmhouse in Buonconvento

Province of Siena / Buonconvento

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden

from £169 / night

£799 / week

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from £169 / night

12

Province of Siena / Montalcino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

from £101 / night

£673 / week

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from £101 / night

8

Holiday apartment in Valiano

Montepulciano / Valiano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly

from £127 / night

£715 / week

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from £127 / night

17

Province of Siena / Montepulciano

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly

from £38 / night

£265 / week

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from £38 / night

15

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £59 / night

£353 - £505 / week

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from £59 / night

24

Province of Siena / Sinalunga

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min

from £43 / night

£295 / week

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from £43 / night

16

Holiday apartment with shared pool in Asciano

Province of Siena / Asciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £127 / night

£564 - £757 / week

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from £127 / night

17

Province of Siena / Cetona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden

Pricing unknown

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Pricing unknown

22

Holiday villa with swimming pool in Sovicille

Province of Siena / Sovicille

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

Pricing unknown

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Pricing unknown

15

Province of Siena / Le Piazze

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £110 / night

£421 - £589 / week

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from £110 / night

29

Siena holiday home rental

Province of Siena / Siena

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly

from £83 / night

£580 - £925 / week

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from £83 / night

8

Holiday apartment letting

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £68 / night

£421 / week

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from £68 / night

15

Holiday apartment with shared pool in Pancole

San Gimignano / Pancole

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £74 / night

£505 - £849 / week

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from £74 / night

14

Province of Siena / Siena

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Pet friendly

from £43 / night

£236 / week

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from £43 / night

20

Holiday apartment rental

Castelnuovo Berardenga / Vagliagli

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £113 / night

£1177 / week

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from £113 / night

22

Murlo holiday apartment rental

Province of Siena / Murlo

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £122 / night

£757 - £958 / week

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from £122 / night

(2) Excellent 

20

Crete Senesi holiday farmhouse rental

Asciano / Crete Senesi

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Child friendly
  • Ask about pets
“Best kept secret!” We stayed at farmhouse with our family 6 adults and 2 children ages 2 and 5. The property was fabulous and met the needs of our grandchildren and children. Location is good but a car is needed in order to get to Sienna and other p
…see more

Pricing unknown

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Pricing unknown

20

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly

from £71 / night

£492 - £799 / week

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from £71 / night

(6) Excellent 

21

Villa rental in Montisi with swimming pool

Province of Siena / Montisi

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £260 / night

£1650 - £2890 / week

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from £260 / night

7

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £122 / night

£841 - £1009 / week

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from £122 / night

9

Holiday apartment in Monticchiello

Pienza / Monticchiello

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min

from £100 / night

£700 / week

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from £100 / night

7

Sinalunga holiday apartment rental

Province of Siena / Sinalunga

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Private garden

Pricing unknown

Book View

Pricing unknown

(1) Average 

12

Holiday apartment with shared pool in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £76 / night

£505 / week

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from £76 / night

28

Holiday apartment in Quercegrossa

Monteriggioni / Quercegrossa

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £118 / night

£824 - £1589 / week

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from £118 / night

10

Province of Siena / Rapolano Terme

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly

from £93 / night

£648 / week

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from £93 / night

32

Province of Siena / Castellina In Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning

from £85 / night

£589 / week

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from £85 / night

12

Holiday apartment with shared pool in Pancole

San Gimignano / Pancole

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £69 / night

£463 - £677 / week

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from £69 / night

(1) Excellent 

38

Radicondoli / Belforte

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 75 km
  • Swimming pool

from £56 / night

£387 - £484 / week

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from £56 / night

13

Province of Siena / San Quirico d'Orcia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £55 / night

£366 - £526 / week

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from £55 / night

1