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

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Province of Siena

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3,549 Holiday homes

48

Fort letting in Montisi with shared pool

Province of Siena / Montisi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £104 / night

£715 - £794 / week

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from £104 / night

(64) Excellent 

52

Holiday villa letting

Province of Siena / Sinalunga

12 26 Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
  • Nearest beach 170 km
  • Swimming pool
  • Child friendly

from £500 / night

£3500 - £7500 / week

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from £500 / 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

£403 / week

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from £58 / night

24

Castelnuovo Berardenga / Pievasciata

1 4 3 nights min

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

from £51 / night

£264 / week

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from £51 / night

80

Farmhouse rental in Castel San Gimignano with shared pool, golf nearby

San Gimignano / Castel San Gimignano

3 7 3 nights min

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

from £185 / night

£1177 - £1849 / week

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from £185 / night

16

Siena / Sant Andrea a Montecchio

1 2 Min stay varies

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

from £59 / night

£409 / week

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from £59 / night

(14) Excellent 

32

Province of Siena / Poggibonsi

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £110 / night

£765 - £1589 / week

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from £110 / night

16

Holiday farmhouse with shared pool in Ponte d'Arbia

Monteroni d'Arbia / Ponte d'Arbia

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £66 / night

£459 - £709 / week

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from £66 / 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

£274 - £317 / week

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from £54 / night

4

San Casciano dei Bagni / Celle sul Rigo

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool

from £60 / night

£417 / week

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from £60 / 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 £227 / night

£1584 - £2005 / week

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from £227 / night

11

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

from £59 / night

£367 / week

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from £59 / night

(1) Excellent 

22

Holiday apartment in Tognazza

Province of Siena / Tognazza

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
“Great location to explore Tuscany from.” Lovely apartment with everything you need to be comfortable. Location was great for exploring Tuscany. Saverio (host) was also very helpful. Would recommend highly.
…see more

from £25 / night

£175 / week

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from £25 / night

20

Holiday farmhouse with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £54 / night

£375 - £625 / week

Enquire View

from £54 / 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 £84 / night

£542 / week

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from £84 / night

(7) Very Good 

27

Radicondoli holiday cottage rental

Province of Siena / Radicondoli

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £50 / night

£334 - £1459 / week

Enquire View

from £50 / night

(3) Average 

20

Province of Siena / Montalcino

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

from £74 / night

£507 / week

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from £74 / night

(6) Excellent 

36

Holiday guest house in Siena

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden

from £47 / night

£421 - £632 / week

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from £47 / night

27

Province of Siena / Murlo

3 6 Min stay varies

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

from £100 / night

£500 - £917 / week

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from £100 / 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 £134 / night

£525 - £892 / week

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from £134 / night

22

Holiday home in Montalcino

Province of Siena / Montalcino

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 80 km
  • Child friendly

from £195 / night

£995 / week

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from £195 / night

5

Province of Siena / Rosia

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Private garden

Pricing unknown

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Pricing unknown

24

Farmhouse rental in Pienza with swimming pool

Province of Siena / Pienza

8 14 7 nights min

  • 8 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £524 / night

£3667 - £6667 / week

Enquire View

from £524 / night

24

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 4 3 nights min

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

from £181 / night

£1110 - £1942 / week

Enquire View

from £181 / night

(8) Excellent 

33

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“Excellent with children or groups” We had very enjoyable stay in a peaceful location with stunning views around. Olimpia was very helpful and everything worked as foreseen. We were trying to find a place with a scent of a history and what would suit b
…see more

from £59 / night

£412 / week

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from £59 / night

20

Cetona holiday farmhouse rental

Province of Siena / Cetona

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £1446 / night

£6667 - £9334 / week

Enquire View

from £1446 / night

(4) Excellent 

28

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £75 / night

£509 - £575 / week

Book View

from £75 / night

(4) Very Good 

16

Radicofani / Contignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Child friendly
  • Pet friendly

from £67 / night

£334 / week

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from £67 / night

23

Torre A Castello holiday farmhouse rental

Province of Siena / Torre A Castello

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden

from £167 / night

£1167 - £1417 / week

Enquire View

from £167 / night

(2) Excellent 

25

Holiday villa in Chiusure

Buonconvento / Chiusure

4 9 6 nights min

  • 4 bedrooms
  • Sleeps 9
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

from £446 / night

£2690 - £3748 / week

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from £446 / night

(11) Excellent 

19

Holiday apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Pet friendly
“Wonderful, Wonderful, Highly Recommended.” My wife and I stayed 23rd. June - 5th. July 2013, and had a wonderful holiday. So relaxing and no hassle whatsoever. The farmhouse has three one bedroomed apartments available and a fourth which Elena (the
…see more

from £75 / night

£467 - £525 / week

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from £75 / 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 £167 / night

£1000 / week

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from £167 / 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

(4) Excellent 

19

Holiday farmhouse with swimming pool in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Farm estate living in Tuscany is pretty special, truly a unforgettable place to stay with fantastic owners” Great place to stay to truly get away and enjoy the relaxing Tuscany life. The chef at home was fantastic and the local shopping 5-10 minutes a
…see more

from £200 / night

£750 - £2100 / week

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from £200 / night

(1) Excellent 

18

Sinalunga holiday apartment rental

Province of Siena / Sinalunga

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly

from £85 / night

£592 - £1042 / week

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from £85 / night

34

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £59 / night

£350 - £675 / week

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from £59 / night

(13) Excellent 

41

Asciano / Crete Senesi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £59 / night

£409 - £684 / week

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from £59 / night

(1) Excellent 

22

Holiday farmhouse with shared pool in Torrita di Siena

Province of Siena / Torrita di Siena

1 3 7 nights min

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

from £34 / night

£234 - £492 / week

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from £34 / night

24

Province of Siena / San Quirico d'Orcia

1 3 Min stay varies

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

from £117 / night

£817 / week

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from £117 / night

31

Murlo / Casciano di Murlo

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £67 / night

£404 - £479 / week

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from £67 / night

1