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Province of Siena Vacation Rentals & Homes - 2436 Rentals Available

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2,436 Vacation rentals

1 / 16

Serre di Rapolano Villa

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$101.00

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from $101.00 / night

1 / 41

Buonconvento Villa

  • 9
  • 16
  • 7 nights min
  • Child friendly

$1,533.00

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from $1,533.00 / night

1 / 19

Serre di Rapolano Villa

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$101.00

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from $101.00 / night

1 / 32

Radda in Chianti Villa

  • 7
  • 13
  • 3 nights min
  • Swimming pool
  • Child friendly

$3,189.00

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from $3,189.00 / night

1 / 17

Serre di Rapolano Villa

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$125.00

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from $125.00 / night

1 / 20

Serre di Rapolano Villa

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$137.00

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from $137.00 / night

1 / 68

Montalcinello Villa

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$443.00

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from $443.00 / night

1 / 42

Chiusure Villa

  • 9
  • 18
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 15 minutes

$1,571.00

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from $1,571.00 / night

(1)

1 / 60

Ciciano Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$321.00

Excellent (1 reviews)

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from $321.00 / night

(8)

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Siena Villa

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$144.00

Excellent (8 reviews)

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from $144.00 / night

(1)

1 / 77

Montalcinello Villa

  • 7
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$526.00

Excellent (1 reviews)

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from $526.00 / night

(6)

1 / 28

Volpaia Villa

  • 6
  • 11
  • 7 nights min
  • Ask about children
  • Ask about pets

Responds fast! Avg. 15 minutes

$486.00

Very Good (6 reviews)

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from $486.00 / night

(3)

1 / 27

Buonconvento Villa

  • 9
  • 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,545.00

Excellent (3 reviews)

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from $1,545.00 / night

1 / 25

Serre di Rapolano Villa

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

$190.00

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from $190.00 / night

1 / 30

Radicofani Villa

  • 10
  • 20
  • 7 nights min
  • Child friendly
  • Pet friendly

$621.00

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from $621.00 / night

1 / 22

Gaiole in Chianti Villa

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$144.00

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from $144.00 / night

(17)

1 / 38

Montepulciano Apartment

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

$133.00

Excellent (17 reviews)

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from $133.00 / night

1 / 32

Siena Villa

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$215.00

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from $215.00 / night

1 / 27

Scrofiano Villa

  • 4
  • 11
  • 7 nights min
  • Child friendly
  • Pet friendly

$81.00

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from $81.00 / night

1 / 93

Cetona Villa

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$478.00

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from $478.00 / night

1 / 31

Costalpino Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$173.00

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from $173.00 / night

1 / 52

Radda in Chianti House

  • 13
  • 50
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$4,097.00

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from $4,097.00 / night

1 / 21

Buonconvento Villa

  • 22
  • 44
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

$15,853.00

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from $15,853.00 / night

1 / 57

Costalpino Villa

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

$209.00

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from $209.00 / night

1 / 62

Farnetella Villa

  • 3
  • 7
  • 7 nights min
  • Child friendly
  • Pet friendly

$362.00

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from $362.00 / night

(1)

1 / 39

Siena Villa

  • 3
  • 6
  • 7 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Ask about children

$253.00

Very Good (1 reviews)

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from $253.00 / night

1 / 32

Montepulciano Villa

  • 4
  • 7
  • 7 nights min
  • Ask about children
  • Ask about pets

Responds fast! Avg. 15 minutes

$309.00

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from $309.00 / night

1 / 35

Ville di Corsano Villa

  • 9
  • 18
  • 7 nights min
  • Child friendly

$2,306.00

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from $2,306.00 / night

(2)

1 / 32

Siena Villa

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$194.00

Excellent (2 reviews)

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from $194.00 / night

1 / 26

Gaiole in Chianti Villa

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

$182.00

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from $182.00 / night

1 / 28

Siena Villa

  • 3
  • 6
  • 7 nights min
  • Nearest beach 190 mi
  • Swimming pool
  • Ask about children

$212.00

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from $212.00 / night

1 / 27

Buonconvento Villa

  • 2
  • 3
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

$88.00

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from $88.00 / night

1 / 27

Monteriggioni Villa

  • 2
  • 6
  • 7 nights min
  • Child friendly
  • Pet friendly

$167.00

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from $167.00 / night

1 / 35

Poggibonsi Villa

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Ask about pets

$82.00

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from $82.00 / night

1 / 24

Abbadia di Montepulciano Villa

  • 4
  • 10
  • 7 nights min
  • Nearest beach 201 mi
  • Swimming pool
  • Child friendly

$318.00

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from $318.00 / night

1 / 46

San Casciano dei Bagni House

  • 8
  • 19
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$526.00

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from $526.00 / night

(1)

1 / 32

Abbadia di Montepulciano Villa

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

Responds fast! Avg. 15 minutes

$369.00

Very Good (1 reviews)

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from $369.00 / night

1 / 27

Gaiole in Chianti Villa

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

$182.00

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from $182.00 / night

1 / 36

Poggibonsi Villa

  • 3
  • 7
  • 7 nights min
  • Child friendly
  • Ask about pets

$95.00

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from $95.00 / night

1 / 17

Poggibonsi Apartment

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$104.00

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from $104.00 / night