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

20

Holiday farmhouse rental

Province of Siena / Siena

1 4 Min stay varies

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

from £81 / night

£563 - £674 / week

Enquire View

from £81 / night

(3) Very Good 

28

Province of Siena / Castelnuovo Berardenga

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning

from £58 / night

£406 / week

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from £58 / night

18

Holiday apartment in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 85 km
  • Child friendly
  • Car not necessary

from £51 / night

£353 / week

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from £51 / night

(1) Excellent 

11

Province of Siena / Castiglione D'Orcia

1 4 Min stay varies

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

from £54 / night

£276 - £320 / week

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from £54 / night

5

Holiday apartment in San Fabiano

Monteroni d'Arbia / San Fabiano

2 4 Min stay varies

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

from £110 / night

£631 - £841 / week

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from £110 / night

24

Montepulciano / Abbadia di Montepulciano

8 7 1 night min

  • 8 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 70 km
  • Child friendly
  • Air conditioning

from £169 / night

£1009 / week

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from £169 / night

4

Province of Siena / Monticiano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly

Pricing unknown

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Pricing unknown

(1) Excellent 

15

Province of Siena / Monteroni d'Arbia

2 4 3 nights min

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

from £55 / night

£353 - £648 / week

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from £55 / night

(8) Excellent 

31

Holiday farmhouse with shared pool in Radicondoli

Radicondoli / Belforte

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Authentic Tuscan Getaway!” This was the perfect getaway destination in the middle of the beautiful tuscan countryside. Although set right up in the hills we found the place first time thanks to the directions from the owners who greeted us with a big
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from £100 / night

£700 / week

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from £100 / night

60

Holiday villa with swimming pool in Bettolle

Sinalunga / Bettolle

11 22 7 nights min

  • 11 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £766 / night

£5358 - £6828 / week

Enquire View

from £766 / night

19

Holiday farmhouse with shared pool in Ulignano

San Gimignano / Ulignano

1 4 Min stay varies

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

from £62 / night

£429 - £698 / week

Enquire View

from £62 / night

(3) Excellent 

24

Poggibonsi / Staggia Senese

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

from £30 / night

£171 - £337 / week

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from £30 / night

36

Radicofani / Contignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

from £59 / night

£421 / week

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from £59 / night

(3) Excellent 

36

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

from £219 / night

£1477 - £4133 / week

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from £219 / night

(7) Excellent 

27

Apartment rental in San Gimignano

Province of Siena / San Gimignano

2 5 3 nights min

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

from £85 / night

£505 / week

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from £85 / night

(4) Very Good 

8

Province of Siena / San Gimignano

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 80 km
  • Car not necessary

from £110 / night

£765 / week

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from £110 / night

(34) Excellent 

24

Apartment rental in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly
“What you imagine when you think "Tuscany"!” We stayed in La Verbena, and it was amazing. Podere Sortoiano is about 15 minutes out of Siena, but it is so worth it to stay out of the city! It's incredibly quiet and relaxing, and the stars are unlike any
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from £42 / night

£267 - £438 / week

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from £42 / night

(2) Excellent 

24

Holiday villa with swimming pool in Montalcinello

Chiusdino / Montalcinello

8 18 7 nights min

  • 8 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly

from £331 / night

£2311 - £3782 / week

Enquire View

from £331 / night

(4) Excellent 

20

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £135 / night

£530 - £900 / week

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from £135 / night

12

Holiday apartment with shared pool in Poggibonsi

Province of Siena / Poggibonsi

1 2 7 nights min

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

from £77 / night

£538 - £639 / week

Enquire View

from £77 / night

83

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £253 / night

£1471 / week

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from £253 / night

14

Castelnuovo Berardenga / Montaperti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £185 / night

£824 - £1849 / week

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from £185 / night

21

Apartment rental in San Gimignano with shared pool

Province of Siena / San Gimignano

1 4 Min stay varies

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

from £76 / night

£530 - £673 / week

Enquire View

from £76 / night

24

Holiday farmhouse letting

Castelnuovo Berardenga / San Gusme

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about pets

from £782 / night

£5471 - £9496 / week

Enquire View

from £782 / night

(1) Excellent 

24

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £73 / night

£463 - £883 / week

Enquire View

from £73 / night

(2) Excellent 

32

Holiday home in Radicofani

Province of Siena / Radicofani

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool

from £51 / night

£337 - £677 / week

Book View

from £51 / night

(2) Very Good 

14

Holiday apartment in Torrita di Siena

Province of Siena / Torrita di Siena

1 3 3 nights min

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

from £59 / night

£215 - £442 / week

Book View

from £59 / night

(1) Excellent 

11

San Rocco a Pilli holiday b&b rental

Sovicille / San Rocco a Pilli

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning

from £93 / night

£583 / week

Book View

from £93 / night

(4) Excellent 

30

Holiday apartment in Siena

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Car not necessary

from £70 / night

£395 - £607 / week

Book View

from £70 / night

(27) Excellent 

28

Holiday apartment in Montisi

Province of Siena / Montisi

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+

from £118 / night

£757 / week

Book View

from £118 / night

(4) Excellent 

18

Farmhouse rental in Radicofani with shared pool

Province of Siena / Radicofani

2 4 Min stay varies

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

from £101 / night

£505 - £715 / week

Book View

from £101 / night

(1) Very Good 

23

San Gimignano / Ulignano

2 6 Min stay varies

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

from £101 / night

£589 - £925 / week

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from £101 / night

11

Torrita di Siena / Montefollonico

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £51 / night

£353 / week

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from £51 / night

19

Sarteano holiday villa rental

Province of Siena / Sarteano

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly

from £540 / night

£3774 - £9572 / week

Enquire View

from £540 / night

20

Holiday manor house rental

Province of Siena / Chiusi

8 21 7 nights min

  • 8 bedrooms
  • Sleeps 21
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool

from £299 / night

£2093 - £3135 / week

Enquire View

from £299 / night

21

Siena / Isola d'Arbia

1 4 Min stay varies

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

from £74 / night

£324 - £800 / week

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from £74 / night

20

Holiday manor house with swimming pool in Pienza

Province of Siena / Pienza

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £630 / night

£4404 - £5505 / week

Enquire View

from £630 / night

(22) Excellent 

60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

from £47 / night

£282 - £408 / week

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from £47 / night

(12) Very Good 

28

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

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Villa PetrAlexa - excellent leisure facility” This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfec
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from £139 / night

£967 - £2017 / week

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from £139 / night

(7) Excellent 

24

Val d'Orcia holiday villa rental

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £229 / night

£1597 - £2022 / week

Book View

from £229 / night

1