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Gaiole in Chianti 2-bedroom Vacation Rentals, Homes & More - 186 Rentals Available.

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186 Vacation rentals

Filters applied: 2+ Bedrooms

Your search has been expanded 19.6 miles to include more rentals

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 / 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)

1 / 127

Tavarnelle Val di Pesa Villa - 15.3 miles away

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

$1,267.00

Very Good (1 reviews)

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from $1,267.00 / night

1 / 33

Figline e Incisa Valdarno Villa - 11.9 miles away

  • 7
  • 14
  • 7 nights min
  • Child friendly

$2,215.00

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from $2,215.00 / night

1 / 21

Castelnuovo Berardenga Villa - 9.1 miles away

  • 9
  • 16
  • 7 nights min
  • Child friendly

$1,268.00

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from $1,268.00 / 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 / 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)

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 10 minutes

$1,280.00

Excellent (1 reviews)

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from $1,280.00 / 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 / 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 / 40

San Casciano in Val di Pesa Villa - 16 miles away

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

$1,331.00

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from $1,331.00 / night

1 / 43

Bucine Villa - 9.1 miles away

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

$778.00

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from $778.00 / night

(10)

1 / 54

Certaldo House - 14 miles away

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

$364.00

Very Good (10 reviews)

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from $364.00 / 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

$872.00

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from $872.00 / night

(34)

1 / 31

San Casciano in Val di Pesa Villa - 17.9 miles away

  • 3
  • 7
  • 3 nights min
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 27 minutes

$119.00

Excellent (34 reviews)

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from $119.00 / night

1 / 76

Tavarnelle Val di Pesa Villa - 13.8 miles away

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

$1,031.00

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from $1,031.00 / 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

(3)

1 / 42

Rignano sull'Arno House - 17.7 miles away

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$645.00

Very Good (3 reviews)

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from $645.00 / 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)

1 / 22

San Gusme Villa - 6.5 miles away

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

$209.00

Excellent (1 reviews)

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from $209.00 / night

(1)

1 / 34

Barberino Val d'Elsa House - 14 miles away

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

$390.00

Excellent (1 reviews)

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from $390.00 / night

(7)

1 / 46

Castellina In Chianti Farmhouse - 7.5 miles away

  • 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

(3)

1 / 33

Castellina In Chianti Farmhouse - 12.2 miles away

  • 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

1 / 21

Siena Apartment - 11.3 miles away

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

Responds fast! Avg. 3 hours 10 minutes

$245.00

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from $245.00 / night

(46)

1 / 43

San Casciano in Val di Pesa House - 18.1 miles away

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

$298.00

Excellent (46 reviews)

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from $298.00 / 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

(1)

1 / 31

Donnini Villa - 18.7 miles away

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

$99.00

Excellent (1 reviews)

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from $99.00 / night

(25)

1 / 15

San Casciano in Val di Pesa House - 15.5 miles away

  • 2
  • 6
  • 3 nights min

Responds fast! Avg. 2 hours 27 minutes

$119.00

Excellent (25 reviews)

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from $119.00 / night

(5)

1 / 36

Castellina In Chianti Farmhouse - 12.2 miles away

  • 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 / 40

Tavarnelle Val di Pesa Villa - 15.3 miles away

  • 10
  • 20
  • 7 nights min
  • Child friendly

$1,346.00

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from $1,346.00 / night

1 / 33

Tavarnelle Val di Pesa Apartment - 14.4 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$139.00

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from $139.00 / night

(1)

1 / 33

Sovicille Villa - 16.7 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly

$981.00

Excellent (1 reviews)

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from $981.00 / night

1 / 28

Tavarnelle Val di Pesa House - 14.5 miles away

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

$391.00

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from $391.00 / night

1 / 34

Lucardo Villa - 17.2 miles away

  • 6
  • 12
  • 7 nights min
  • Child friendly

$807.00

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from $807.00 / night

(2)

1 / 39

Castellina In Chianti Farmhouse - 12.2 miles away

  • 4
  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$273.00

Very Good (2 reviews)

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from $273.00 / night

1 / 20

Pergine Valdarno Apartment - 12.6 miles away

  • 3
  • 5
  • 7 nights min
  • Ask about children
  • Pet friendly

$137.00

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from $137.00 / night

1 / 44

Marcialla Apartment - 18.2 miles away

  • 3
  • 30
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$2,360.00

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from $2,360.00 / night

1 / 20

Monteriggioni House - 11.9 miles away

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

$234.00

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from $234.00 / night

1 / 50

Certaldo Villa - 18.2 miles away

  • 2
  • 5
  • 7 nights min
  • Ask about children
  • Ask about pets

$199.00

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from $199.00 / night

1 / 35

Tavarnelle Val di Pesa Apartment - 14.4 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$139.00

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from $139.00 / night