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

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Province of Siena

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3,754 Holiday homes

(1) Average 

10

Province of Siena / Colle di Val d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask owner if suitable for children
  • Ask about pets

from £119 / night

£831 / week

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from £119 / night

18

Holiday apartment in Sant'Albino

Montepulciano / Sant'Albino

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £56 / night

£386 / week

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from £56 / night

19

Farmhouse rental in San Casciano dei Bagni with swimming pool

Province of Siena / San Casciano dei Bagni

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £236 / night

£1373 - £2975 / week

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from £236 / night

21

Apartment rental in Casole d'Elsa with swimming pool

Province of Siena / Casole d'Elsa

2 4 Min stay varies

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

from £85 / night

£484 - £763 / week

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from £85 / night

12

Castiglione D'Orcia holiday villa rental

Province of Siena / Castiglione D'Orcia

8 25 Min stay varies

  • 8 bedrooms
  • Sleeps 25
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £364 / night

£2543 - £4238 / week

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from £364 / night

24

Colle di Val d'Elsa holiday apartment rental

Colle di Val d'Elsa / Campiglia dei Foci

2 6 7 nights min

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

from £71 / night

£496 - £806 / week

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from £71 / night

14

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Car not necessary

from £68 / night

£424 - £551 / week

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from £68 / night

13

Province of Siena / Radicondoli

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

from £103 / night

£721 - £804 / week

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from £103 / night

43

Villa letting in Sarteano with swimming pool

Province of Siena / Sarteano

10 17 1 night min

  • 10 bedrooms
  • Sleeps 17
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £339 / night

£2373 / week

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from £339 / night

37

Province of Siena / Radicondoli

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Nearest beach 65 km
  • Child friendly
  • Ask about pets

from £153 / night

£890 - £1128 / week

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from £153 / night

8

Casole d'Elsa holiday farmhouse rental

Casole d'Elsa / Monteguidi

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £60 / night

£422 - £605 / week

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from £60 / night

21

Holiday guest house in Gaiole in Chianti

Gaiole in Chianti / Montefienali

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden

from £46 / night

£263 / week

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from £46 / night

18

Holiday apartment in Pienza

Province of Siena / Pienza

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £153 / night

£1068 / week

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from £153 / night

(11) Excellent 

43

Holiday villa in Staggia Senese

Poggibonsi / Staggia Senese

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“Best vacation ever!” Our entire experience at Villa Vianci was beyond expectations. We travelled with 4 generations, ages 3 1/2 to 85! The villa was spectacular, spacious & immaculate. The pictures on line don't do it justice. Tommasso & Chiara we
…see more

from £509 / night

£3560 / week

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from £509 / night

20

Ponte a Bozzone holiday farmhouse rental

Castelnuovo Berardenga / Ponte a Bozzone

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £256 / night

£1500 - £2500 / week

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from £256 / night

23

Holiday farmhouse with shared pool in Chiusure

Buonconvento / Chiusure

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £139 / night

£806 - £1441 / week

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from £139 / night

20

Holiday villa with swimming pool in Radicofani

Province of Siena / Radicofani

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet 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 £111 / night

£424 - £594 / week

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from £111 / 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 £75 / night

£509 - £856 / week

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from £75 / night

(7) Very Good 

15

Province of Siena / Chiusdino

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 30 km
  • Child friendly
  • Pet friendly

Pricing unknown

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Pricing unknown

(1) Excellent 

15

Holiday apartment with swimming pool in Radicofani

Province of Siena / Radicofani

1 4 Min stay varies

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

from £68 / night

£399 - £636 / week

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from £68 / night

22

Villa rental in San Giovanni d'Asso with swimming pool

Province of Siena / San Giovanni d'Asso

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £686 / night

£4800 - £5850 / week

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from £686 / night

16

Holiday cottage with shared pool in Poggibonsi

Province of Siena / Poggibonsi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £68 / night

£467 - £653 / week

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from £68 / night

24

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa / Campiglia dei Foci

2 6 7 nights min

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

from £66 / night

£462 - £780 / week

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from £66 / night

12

Province of Siena / Montalcino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

from £102 / night

£678 / week

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from £102 / night

26

Province of Siena / Asciano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £60 / night

£416 / week

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from £60 / night

4

Province of Siena / Casole d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Private garden

from £85 / night

£678 / week

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from £85 / night

47

Radicondoli / Belforte

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 75 km
  • Child friendly
  • Pet friendly

from £76 / night

£532 - £629 / week

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from £76 / night

24

Castelnuovo Berardenga / Casal Monastero

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

Pricing unknown

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Pricing unknown

(1) Very Good 

16

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden

from £85 / night

£424 / week

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from £85 / night

19

Province of Siena / Gaiole in Chianti

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

from £356 / night

£1272 / week

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from £356 / 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

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Pricing unknown

15

San Casciano dei Bagni holiday apartment rental

Province of Siena / San Casciano dei Bagni

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

Pricing unknown

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Pricing unknown

10

Province of Siena / Castelnuovo Berardenga

8 32 Min stay varies

  • 8 bedrooms
  • Sleeps 32
  • Min stay varies
  • Air conditioning
  • Private garden

Pricing unknown

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Pricing unknown

4

Province of Siena / Chiusi

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

Pricing unknown

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Pricing unknown

(4) Excellent 

24

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £152 / night

£1060 - £2331 / week

Enquire View

from £152 / night

24

Province of Siena / San Quirico d'Orcia

2 4 Min stay varies

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

from £154 / night

£1074 / week

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from £154 / night

22

Holiday apartment with shared pool in Crete Senesi

Asciano / Crete Senesi

1 4 Min stay varies

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

from £85 / night

£339 - £755 / week

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from £85 / night

20

Holiday apartment with shared pool in Asciano

Province of Siena / Asciano

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £187 / night

£789 - £1085 / week

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from £187 / night

20

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

from £57 / night

£399 - £645 / week

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from £57 / night

1