Holiday castles in Province of Siena

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Province of Siena

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12 Holiday homes

Filters applied: Castle

Travellers going to Province of Siena are booking June dates now. Secure your holiday home today and have the perfect trip.

46

Holiday castle rental

Province of Siena / Poggibonsi

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Enchanting Winery At the top of a hill with 309 hectares between wood, olive trees and wine yards is located this enchanting winery, with it’s amazing medioeval castle, the pool villa, the farmhouse and a real good Chianti wine production. This property is the ch  …see more

from £513 / night

£3590 - £4906 / week

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from £513 / night

16

Holiday castle with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Relais chianti, luxury apartment chianti, hamlet chianti, medieval village, infinity swimming pool ,outdoor dining area , barbecue grill.  …see more

from £127 / night

£1490 / week

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from £127 / night

(1) Average 

24

Province of Siena / Poggibonsi

7 12 3 nights min

  • 7 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

 …see more

from £428 / night

£2992 / week

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from £428 / night

Featured properties

33

Holiday castle rental

Province of Siena / San Giovanni d'Asso

4 9 3 nights min

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Welcome at Montelifrè's castle Montelifrè is a medieval village still owned by the ancient and noble family Martinozzi.The hamlet is one of the oldest military buildings in Crete senesi and Valdorcia, in Tuscany, one ofthe most beautiful italian regio  …see more

from £39 / night

£171 - £2086 / week

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from £39 / night

9

Province of Siena / Castelnuovo Berardenga

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £154 / night

£1077 / week

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from £154 / night

66

Province of Siena / Gaiole in Chianti

4 7 7 nights min

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

 …see more

from £285 / night

£1992 - £3496 / week

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from £285 / night

53

Province of Siena / Cetona

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Suitable for children age 5+

 …see more

from £1483 / night

£6838 - £9573 / week

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from £1483 / night

29

Province of Siena / Gaiole in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £146 / night

£988 - £1795 / week

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from £146 / night

27

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £189 / night

£1155 - £1371 / week

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from £189 / night

39

Province of Siena / Gaiole in Chianti

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £223 / night

£1412 - £1670 / week

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from £223 / night

33

Province of Siena / Gaiole in Chianti

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £242 / night

£1544 - £3590 / week

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from £242 / night

33

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Suitable for children age 5+

 …see more

from £242 / night

£1544 - £2992 / week

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from £242 / night