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Province of Siena 2-bedroom Vacation Rentals, Homes & More - 238 Rentals Available.

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238 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 41

Buonconvento Villa

  • 9
  • 18
  • 7 nights min
  • Child friendly

$1,856.00

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from $1,856.00 / night

1 / 35

Ville di Corsano Villa

  • 9
  • 18
  • 7 nights min
  • Child friendly

$2,421.00

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from $2,421.00 / night

(17)

1 / 38

Montepulciano Apartment

  • 2
  • 6
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$131.00

Excellent (17 reviews)

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from $131.00 / night

(9)

1 / 34

Montepulciano Apartment

  • 3
  • 6
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$131.00

Very Good (9 reviews)

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from $131.00 / night

1 / 12

Pievescola Villa

  • 2
  • 4
  • min stay varies
  • Child friendly

$1,412.00

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from $1,412.00 / night

1 / 37

San Casciano dei Bagni Villa

  • 9
  • 18
  • 7 nights min
  • Child friendly

$3,229.00

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from $3,229.00 / night

(34)

1 / 46

Montalcino Farmhouse

  • 3
  • 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$343.00

Very Good (34 reviews)

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from $343.00 / night

1 / 22

San Casciano dei Bagni Villa

  • 7
  • 14
  • 7 nights min
  • Child friendly

$1,453.00

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from $1,453.00 / night

1 / 18

Montalcino Apartment

  • 2
  • 4
  • 2 nights min
  • Nearest beach 137 mi
  • Swimming pool
  • Child friendly

$342.00

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from $342.00 / night

(1)

1 / 29

Castelnuovo dell'Abate Villa

  • 5
  • 8
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$1,478.00

Excellent (1 reviews)

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from $1,478.00 / night

(11)

1 / 33

Montepulciano Apartment

  • 2
  • 5
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$114.00

Excellent (11 reviews)

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from $114.00 / night

1 / 19

San Casciano dei Bagni Villa

  • 7
  • 14
  • 7 nights min
  • Child friendly
  • Ask about pets

$2,768.00

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from $2,768.00 / night

1 / 21

Castelnuovo Berardenga Villa

  • 9
  • 16
  • 7 nights min
  • Child friendly

$1,268.00

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from $1,268.00 / night

(2)

1 / 39

Montepulciano Apartment

  • 2
  • 6
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$131.00

Excellent (2 reviews)

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from $131.00 / night

1 / 37

San Gimignano Villa

  • 8
  • 16
  • min stay varies
  • Child friendly
  • Ask about pets

$1,776.00

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from $1,776.00 / night

1 / 20

Montalcino Apartment

  • 2
  • 6
  • 2 nights min
  • Nearest beach 137 mi
  • Swimming pool
  • Child friendly

$419.00

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from $419.00 / night

1 / 35

Castelmuzio Villa

  • 2
  • 6
  • min stay varies
  • Nearest beach 161 mi
  • Swimming pool
  • Child friendly

$166.00

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from $166.00 / night

1 / 11

Pievescola Villa

  • 3
  • 6
  • min stay varies
  • Child friendly

$1,412.00

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from $1,412.00 / night

(3)

1 / 25

Montepulciano Apartment

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Pet friendly

$133.00

Excellent (3 reviews)

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from $133.00 / night

(1)

1 / 22

San Gusme Villa

  • 2
  • 6
  • 7 nights min
  • Nearest beach 185 mi
  • Swimming pool
  • Child friendly

$208.00

Excellent (1 reviews)

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from $208.00 / night

1 / 27

Pienza Villa

  • 6
  • 12
  • min stay varies
  • Child friendly

$971.00

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from $971.00 / night

1 / 18

Montalcino Apartment

  • 2
  • 4
  • 2 nights min
  • Nearest beach 137 mi
  • Swimming pool
  • Child friendly

$331.00

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from $331.00 / night

1 / 33

Ponte a Bozzone Villa

  • 5
  • 10
  • 7 nights min
  • Child friendly

$2,249.00

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from $2,249.00 / night

1 / 20

San Giovanni d'Asso Villa

  • 7
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 3 minutes

$779.00

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from $779.00 / night

(5)

1 / 70

Monteriggioni House

  • 17
  • 34
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$4,017.00

Excellent (5 reviews)

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from $4,017.00 / night

(1)

1 / 148

Pienza Villa

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 3 minutes

$615.00

Excellent (1 reviews)

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from $615.00 / night

(1)

1 / 34

Sant'Albino Villa

  • 7
  • 21
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly

$568.00

Excellent (1 reviews)

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from $568.00 / night

(3)

1 / 33

Castellina In Chianti Farmhouse

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$201.00

Very Good (3 reviews)

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from $201.00 / night

(7)

1 / 46

Castellina In Chianti Farmhouse

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$469.00

Very Good (7 reviews)

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from $469.00 / night

1 / 29

Pienza Villa

  • 8
  • 14
  • min stay varies
  • Child friendly
  • Ask about pets

$971.00

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from $971.00 / night

1 / 21

Siena Apartment

  • 2
  • 4
  • 3 nights min
  • Ask about children
  • Air conditioning

Responds fast! Avg. 3 hours 10 minutes

$243.00

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from $243.00 / night

(1)

1 / 47

Pienza House

  • 7
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$1,200.00

Very Good (1 reviews)

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from $1,200.00 / night

1 / 33

Montefollonico Villa

  • 5
  • 10
  • 7 nights min
  • Ask about children
  • Ask about pets

$1,037.00

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from $1,037.00 / night

(1)

1 / 33

Sovicille Villa

  • 4
  • 8
  • 7 nights min
  • Child friendly

$982.00

Excellent (1 reviews)

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from $982.00 / night

(5)

1 / 36

Castellina In Chianti Farmhouse

  • 3
  • 7
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$175.00

Very Good (5 reviews)

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from $175.00 / night

1 / 54

San Lorenzo a Merse Villa

  • 14
  • 27
  • 7 nights min
  • Child friendly

$3,596.00

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from $3,596.00 / night

1 / 26

Castelmuzio Villa

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$572.00

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from $572.00 / night

1 / 52

Cetona Villa

  • 8
  • 16
  • 7 nights min
  • Child friendly

$2,906.00

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from $2,906.00 / night

1 / 20

Buonconvento Apartment

  • 2
  • 3
  • 7 nights min
  • Ask about children
  • Pet friendly

$110.00

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from $110.00 / night

1 / 20

Poggibonsi House

  • 6
  • 11
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$928.00

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from $928.00 / night