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Gaiole in Chianti Vacation Rentals & Homes - 276 Rentals Available

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276 Vacation rentals

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1 / 35

Ville di Corsano Villa - 17.5 miles away

  • 9
  • 18
  • 7 nights min
  • Child friendly

$2,421.00

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from $2,421.00 / night

1 / 14

Grassina Apartment - 19.1 miles away

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

$234.00

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from $234.00 / night

1 / 37

Castiglion Fibocchi Villa - 16 miles away

  • 9
  • 18
  • min stay varies
  • Child friendly

$1,907.00

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from $1,907.00 / night

1 / 56

Tavarnelle Val di Pesa Villa - 14.5 miles away

  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,371.00

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from $1,371.00 / night

1 / 20

Grassina Apartment - 19.1 miles away

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

$359.00

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from $359.00 / night

1 / 39

Impruneta Villa - 17.5 miles away

  • 20
  • 40
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$7,598.00

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from $7,598.00 / night

1 / 12

Grassina Apartment - 19.1 miles away

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

$250.00

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from $250.00 / night

1 / 18

Grassina Apartment - 19.1 miles away

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

$234.00

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from $234.00 / night

1 / 29

Reggello Villa - 15.6 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$888.00

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from $888.00 / night

1 / 43

Bucine Villa - 9.1 miles away

  • 9
  • 18
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$719.00

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from $719.00 / night

(33)

1 / 34

San Casciano in Val di Pesa Apartment - 18.1 miles away

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

$270.00

Excellent (33 reviews)

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from $270.00 / night

1 / 10

Grassina Apartment - 19.1 miles away

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

$176.00

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from $176.00 / night

(1)

1 / 127

Tavarnelle Val di Pesa Villa - 15.3 miles away

  • 11
  • 20
  • 7 nights min
  • Nearest beach 145 mi
  • Swimming pool
  • Child friendly

$1,268.00

Very Good (1 reviews)

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from $1,268.00 / night

(1)

1 / 41

Ambra House - 7 miles away

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

$913.00

Excellent (1 reviews)

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from $913.00 / night

1 / 76

Tavarnelle Val di Pesa Villa - 13.8 miles away

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

$951.00

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from $951.00 / night

(34)

1 / 31

San Casciano in Val di Pesa Villa - 17.9 miles away

  • 3
  • 7
  • min stay varies
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 19 minutes

$119.00

Excellent (34 reviews)

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from $119.00 / night

1 / 33

Figline e Incisa Valdarno Villa - 11.9 miles away

  • 7
  • 14
  • 7 nights min
  • Child friendly

$2,768.00

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from $2,768.00 / night

(10)

1 / 54

Certaldo House - 14 miles away

  • 7
  • 15
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$319.00

Very Good (10 reviews)

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from $319.00 / night

1 / 40

San Casciano in Val di Pesa Villa - 16 miles away

  • 11
  • 15
  • min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly

$1,332.00

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from $1,332.00 / night

1 / 29

San Polo in Chianti Villa - 14.6 miles away

  • 5
  • 12
  • 7 nights min

$1,442.00

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from $1,442.00 / night

1 / 21

Castelnuovo Berardenga Villa - 9.1 miles away

  • 9
  • 16
  • 7 nights min
  • Child friendly

$968.00

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from $968.00 / night

1 / 36

Rignano sull'Arno Villa - 18.2 miles away

  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$825.00

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from $825.00 / night

1 / 37

San Gimignano Villa - 19.6 miles away

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

$1,776.00

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from $1,776.00 / night

1 / 32

San Donato in Poggio Villa - 10.7 miles away

  • 5
  • 12
  • 7 nights min
  • Nearest beach 209 mi
  • Swimming pool
  • Child friendly

$871.00

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from $871.00 / night

1 / 34

Ponte a Bozzone Villa - 9.5 miles away

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

$1,134.00

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from $1,134.00 / night

1 / 13

Grassina Apartment - 19.1 miles away

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

$176.00

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from $176.00 / night

(1)

1 / 32

San Casciano in Val di Pesa Villa - 16 miles away

  • 11
  • 20
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 3 hours 37 minutes

$1,108.00

Excellent (1 reviews)

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from $1,108.00 / night

1 / 10

Grassina Apartment - 19.1 miles away

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

$234.00

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from $234.00 / night

1 / 28

Lucardo Apartment - 18.5 miles away

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

$241.00

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from $241.00 / night

1 / 33

Ponte a Bozzone Villa - 8.2 miles away

  • 5
  • 10
  • 7 nights min
  • Child friendly

$2,249.00

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from $2,249.00 / night

1 / 33

Barberino Val d'Elsa Villa - 15.5 miles away

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

$999.00

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from $999.00 / night

1 / 65

Barberino Val d'Elsa Villa - 14 miles away

  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,741.00

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from $1,741.00 / night

1 / 56

Impruneta Villa - 17.3 miles away

  • 9
  • 14
  • 7 nights min
  • Child friendly

$1,522.00

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from $1,522.00 / night

1 / 15

Grassina Apartment - 19.1 miles away

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

$250.00

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from $250.00 / night

1 / 17

Grassina Apartment - 19.1 miles away

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

$250.00

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from $250.00 / night

1 / 38

Tavarnelle Val di Pesa Villa - 14.5 miles away

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

$474.00

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from $474.00 / night

1 / 12

Grassina Apartment - 19.1 miles away

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

$146.00

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from $146.00 / night

1 / 13

Taverne d'Arbia Villa - 10.6 miles away

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

$570.00

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from $570.00 / night

1 / 14

Grassina Apartment - 19.1 miles away

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

$250.00

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from $250.00 / night

(5)

1 / 70

Monteriggioni House - 12.4 miles away

  • 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