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Province of Siena Vacation Rentals & Homes - 2100 Rentals Available

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2,100 Vacation rentals

1 / 41

Siena House

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$355.00

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from $355.00 / night

(2)

1 / 32

Siena Villa

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

$210.00

Excellent (2 reviews)

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from $210.00 / night

1 / 33

Castellina In Chianti House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

$318.00

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from $318.00 / night

1 / 24

Castelmuzio Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children

$504.00

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from $504.00 / night

1 / 20

Monastero d'Ombrone Villa

  • 8
  • 16
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

$1,269.00

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from $1,269.00 / night

1 / 12

San Giovanni d'Asso House

  • 4
  • 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$606.00

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from $606.00 / night

(6)

1 / 40

Siena Villa

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

$156.00

Excellent (6 reviews)

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from $156.00 / night

(1)

1 / 48

Castellina In Chianti Villa

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

$630.00

Excellent (1 reviews)

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from $630.00 / night

(1)

1 / 40

Pancole Apartment

  • 1
  • 2
  • 7 nights min
  • Ask about children

$98.00

Excellent (1 reviews)

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from $98.00 / night

1 / 20

Chianciano Terme House

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

$662.00

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from $662.00 / night

1 / 46

Chianciano Terme Apartment

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Ask about children

$135.00

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from $135.00 / night

1 / 41

Chianciano Terme House

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

$757.00

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from $757.00 / night

1 / 32

Radda in Chianti Farmhouse

  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$592.00

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from $592.00 / night

(1)

1 / 60

Montepulciano Villa

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

$471.00

Excellent (1 reviews)

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from $471.00 / night

(3)

1 / 44

Siena Villa

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

$346.00

Excellent (3 reviews)

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from $346.00 / night

1 / 25

San Gimignano Apartment

  • 4
  • 8
  • Min stay varies
  • Ask about children
  • Ask about pets

$260.00

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from $260.00 / night

1 / 44

Lecchi in Chianti Villa

  • 3
  • 8
  • Min stay varies
  • Child friendly
  • Ask about pets

$475.00

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from $475.00 / night

1 / 37

Staggia Villa

  • 7
  • 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$655.00

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from $655.00 / night

1 / 16

San Gimignano Villa

  • 9
  • 15
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$583.00

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from $583.00 / night

(2)

1 / 48

Siena Villa

  • 5
  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$374.00

Excellent (2 reviews)

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from $374.00 / night

1 / 26

Siena House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$433.00

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from $433.00 / night

1 / 35

Quercegrossa Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$709.00

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from $709.00 / night

1 / 49

Chianciano Terme Apartment

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children

$270.00

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from $270.00 / night

1 / 26

Gaiole in Chianti Villa

  • 6
  • 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$621.00

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from $621.00 / night

1 / 45

Colle di Val d'Elsa House

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

$318.00

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from $318.00 / night

(1)

1 / 32

Lucarelli Villa

  • 6
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$527.00

Excellent (1 reviews)

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from $527.00 / night

1 / 47

Siena Villa

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$311.00

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from $311.00 / night

1 / 44

San Gimignano Apartment

  • 1
  • 3
  • 7 nights min
  • Ask about children

$98.00

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from $98.00 / night

1 / 34

Poggibonsi Villa

  • 3
  • 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets

$824.00

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from $824.00 / night

1 / 48

Chianciano Terme Apartment

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

$193.00

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from $193.00 / night

1 / 20

Radda in Chianti Villa

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$353.00

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from $353.00 / night

1 / 12

Pienza Apartment

  • 1
  • 4
  • 2 nights min
  • Ask about children
  • Ask about pets

$107.00

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from $107.00 / night

1 / 31

Monastero d'Ombrone Apartment

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$299.00

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from $299.00 / night

(7)

1 / 24

San Gimignano Apartment

  • 2
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$240.00

Excellent (7 reviews)

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from $240.00 / night

1 / 59

Radda in Chianti Villa

  • 3
  • 6
  • Min stay varies
  • Child friendly
  • Pet friendly

$415.00

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from $415.00 / night

(5)

1 / 71

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 / 19

San Gimignano Apartment

  • 3
  • 6
  • Min stay varies
  • Ask about children
  • Ask about pets

$214.00

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from $214.00 / night

1 / 12

Chianciano Terme Villa

  • 3
  • 6
  • 7 nights min
  • Ask about children

$380.00

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from $380.00 / night

1 / 79

Pancole Villa

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$397.00

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from $397.00 / night

1 / 20

San Gimignano House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$186.00

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from $186.00 / night