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

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Province of Siena

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3,758 Holiday homes

(6) Very Good 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Peaceful taste of Tuscany!!!!” Stayed here for a lovely, idyllic, December week. Amazing apartment with all home comforts. Loved walking through the village, stopping for pizza and fine wines :-) The views over the hills and vineyards are incredibly i
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from £150 / night

£600 / week

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from £150 / night

(4) Excellent 

16

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

from £76 / night

£404 - £841 / week

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Responds fast!
avg. 2 hours 7 minutes

from £76 / night

(6) Very Good 

24

Cottage rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Peace and tranquility” My wife and I stayed here in June 2012. On arrival we were stuned by how beautiful the house, the grounds and the surrounding valleys were. The gardens are well maintained as with the house. There are numerous sitting areas outs
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from £73 / night

£505 - £1471 / week

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from £73 / night

(1) Excellent 

13

Province of Siena / San Giovanni d'Asso

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly

from £76 / night

£505 - £547 / week

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Responds fast!
avg. 1 hour 14 minutes

from £76 / night

(6) Excellent 

39

Farmhouse rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly

from £74 / night

£429 - £463 / week

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Responds fast!
avg. 2 hours 28 minutes

from £74 / night

(1) Very Good 

21

Province of Siena / Siena

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Air conditioning

from £134 / night

£936 / week

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from £134 / night

20

Province of Siena / Montepulciano

2 6 3 nights min

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

from £59 / night

£505 - £858 / week

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from £59 / night

(1) Excellent 

24

Holiday villa with swimming pool in Poggibonsi

Province of Siena / Poggibonsi

7 18 7 nights min

  • 7 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £232 / night

£1622 - £3908 / week

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from £232 / night

29

Province of Siena / Rapolano Terme

3 6 1 night min

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

from £85 / night

£547 / week

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from £85 / night

28

Sinalunga holiday villa rental

Province of Siena / Sinalunga

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £119 / night

£832 - £1614 / week

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from £119 / night

(1) Excellent 

22

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £250 / night

£1750 - £2460 / week

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from £250 / night

11

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

Province of Siena / Colle di Val d'Elsa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £101 / night

£589 - £925 / week

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from £101 / night

(2) Very Good 

35

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from £127 / night

£715 - £832 / week

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from £127 / night

(6) Very Good 

24

Holiday apartment rental

Siena / Val di Merse

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly

from £169 / night

£925 - £1177 / week

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from £169 / night

(9) Very Good 

41

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Stunning Views” We had a most enjoyable time at this house and would recommend it for its location and closeness to Montepulciano. The house was delightful and the views across the valley and surrounding countryside were excellent. We can recommend
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from £100 / night

£625 - £895 / week

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from £100 / night

(4) Very Good 

14

Poggibonsi holiday apartment rental

Province of Siena / Poggibonsi

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £51 / night

£353 - £522 / week

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Responds fast!
avg. 3 hours 59 minutes

from £51 / night

(1) Very Good 

7

Castelnuovo Berardenga / Pianella

6 20 Min stay varies

  • 6 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Air conditioning

Pricing unknown

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Pricing unknown

26

San Gimignano / Castel San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets

from £47 / night

£286 - £522 / week

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from £47 / night

(6) Excellent 

19

Holiday farmhouse in San Fabiano

Monteroni d'Arbia / San Fabiano

6 20 Min stay varies

  • 6 bedrooms
  • Sleeps 20
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £622 / night

£3614 - £4874 / week

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from £622 / night

7

Holiday apartment in Bettolle

Sinalunga / Bettolle

2 4 1 night min

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

from £43 / night

£337 / week

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Responds fast!
avg. 3 hours 39 minutes

from £43 / night

20

Holiday farmhouse rental

Province of Siena / San Gimignano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about pets

from £310 / night

£2169 - £3353 / week

Enquire View

Responds fast!
avg. 42 minutes

from £310 / night

24

Province of Siena / Castellina In Chianti

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 85 km
  • Child friendly
  • Private garden

from £59 / night

£412 / week

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from £59 / night

9

Province of Siena / Ville di Corsano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

Pricing unknown

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Pricing unknown

31

Montepulciano holiday villa let

Province of Siena / Montepulciano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Private garden

from £159 / night

£1110 - £2051 / week

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from £159 / night

(1) Excellent 

23

Holiday villa with shared pool in Montepulciano

Province of Siena / Montepulciano

4 2 Min stay varies

  • 4 bedrooms
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Ask owner if suitable for children
“Old-world Italian charm in a beautiful Tuscan setting” It's a job to find it it, but once you do, you'll want to stay longer than you've booked for. The house has been in the family since 1812 - they produce their own wine - and Olimpia is a charming
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from £30 / night

£206 / week

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Responds fast!
avg. 1 hour 50 minutes

from £30 / night

20

Holiday home in Buonconvento

Province of Siena / Buonconvento

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £948 / night

£3790 - £6121 / week

Enquire View

from £948 / night

17

Province of Siena / Abbadia San Salvatore

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ski
  • Child friendly
  • Private garden

from £76 / night

£421 - £505 / week

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Responds fast!
avg. 2 hours 54 minutes

from £76 / night

23

Holiday farmhouse with shared pool in Larniano

San Gimignano / Larniano

3 6 Min stay varies

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

from £211 / night

£1234 - £1967 / week

Enquire View

Responds fast!
avg. 42 minutes

from £211 / night

(4) Excellent 

19

Province of Siena / Torrita di Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden

from £75 / night

£484 / week

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Responds fast!
avg. 3 hours 2 minutes

from £75 / night

17

Holiday apartment in Castel San Gimignano

San Gimignano / Castel San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly

from £38 / night

£253 / week

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from £38 / night

15

Holiday farmhouse rental

Province of Siena / Radicofani

1 2 Min stay varies

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

from £59 / night

£328 - £437 / week

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from £59 / night

19

Holiday farmhouse with swimming pool in Palazzone

Province of Siena / Palazzone

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £765 / night

£5351 - £7781 / week

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Responds fast!
avg. 42 minutes

from £765 / night

(14) Excellent 

25

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly

from £76 / night

£398 - £449 / week

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Responds fast!
avg. 1 hour 54 minutes

from £76 / night

16

Contignano holiday villa rental

Radicofani / Contignano

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Pricing unknown

Enquire View

Pricing unknown

100

Holiday villa with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £1141 / night

£7984 - £10085 / week

Enquire View

from £1141 / night

(4) Excellent 

36

Holiday farmhouse in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly

from £93 / night

£547 - £589 / week

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Responds fast!
avg. 2 hours 28 minutes

from £93 / night

21

Castellina In Chianti holiday farmhouse rental

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £111 / night

£653 - £1095 / week

Enquire View

Responds fast!
avg. 42 minutes

from £111 / night

15

Chiusdino / Ciciano

1 2 5 nights min

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

from £68 / night

£589 / week

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from £68 / night

20

Holiday farmhouse with swimming pool in Guazzino

Sinalunga / Guazzino

11 20 Min stay varies

  • 11 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £799 / night

£4664 - £6988 / week

Enquire View

Responds fast!
avg. 42 minutes

from £799 / night

(3) Very Good 

20

Province of Siena / Siena

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly

from £68 / night

£395 - £664 / week

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from £68 / night

1