Search 105,200+ Vacation Rentals

Castellina In Chianti Vacation Rentals & Homes - 315 Rentals Available

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

315 Vacation rentals

(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)

Inquire

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)

Inquire

from $469.00 / 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)

Inquire

from $175.00 / night

1 / 34

Castellina In Chianti Villa

  • 7
  • 14
  • 7 nights min
  • Child friendly

$987.00

Inquire

from $987.00 / night

(2)

1 / 39

Castellina In Chianti Farmhouse

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

$273.00

Very Good (2 reviews)

Inquire

from $273.00 / night

(18)

1 / 26

Castellina In Chianti House

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

$469.00

Excellent (18 reviews)

Inquire

from $469.00 / night

1 / 22

Castellina In Chianti Villa

  • 5
  • 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,078.00

Inquire

from $2,078.00 / night

1 / 35

Castellina In Chianti Farmhouse

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

$823.00

Inquire

from $823.00 / night

Your search has been expanded 17.1 miles to include more rentals

1 / 18

Greve in Chianti Villa - 8 miles away

  • 5
  • 8
  • 7 nights min
  • Ask about children
  • Ask about pets

$519.00

Inquire

from $519.00 / night

1 / 51

Certaldo Apartment - 11.6 miles away

  • 1
  • 2
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$182.00

Inquire

from $182.00 / night

1 / 60

Barberino Val d'Elsa Apartment - 7.4 miles away

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

$394.00

Inquire

from $394.00 / night

1 / 46

Gambassi Terme Apartment - 14.5 miles away

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

$190.00

Inquire

from $190.00 / night

1 / 51

Montebenichi Cottage - 16.3 miles away

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

$717.00

Inquire

from $717.00 / night

1 / 55

Barberino Val d'Elsa Apartment - 7.7 miles away

  • 5
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$263.00

Inquire

from $263.00 / night

(1)

1 / 22

San Gusme Villa - 12.4 miles away

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

$212.00

Excellent (1 reviews)

Inquire

from $212.00 / night

1 / 20

Poggibonsi House - 5.4 miles away

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

$928.00

Inquire

from $928.00 / night

1 / 86

Poggibonsi Villa - 6.5 miles away

  • 3
  • 8
  • 7 nights min
  • Nearest beach 125 mi
  • Swimming pool
  • Child friendly

$717.00

Inquire

from $717.00 / night

1 / 29

San Donato in Poggio Cottage - 4.8 miles away

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

$222.00

Inquire

from $222.00 / night

1 / 77

Marcialla House - 11.2 miles away

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

$955.00

Inquire

from $955.00 / night

1 / 20

Monastero d'Ombrone Villa - 17.1 miles away

  • 7
  • 14
  • 7 nights min
  • Child friendly

$505.00

Inquire

from $505.00 / night

1 / 111

Siena Villa - 10.6 miles away

  • 6
  • 12
  • min stay varies
  • Nearest beach 161 mi
  • Swimming pool
  • Child friendly

$596.00

Inquire

from $596.00 / night

1 / 32

San Donato in Poggio Apartment - 4.8 miles away

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

$269.00

Inquire

from $269.00 / night

1 / 32

Montefiridolfi Villa - 10.5 miles away

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

Responds fast! Avg. 2 hours 38 minutes

$669.00

Book

from $669.00 / night

1 / 56

Barberino Val d'Elsa Apartment - 7.5 miles away

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$284.00

Inquire

from $284.00 / night

1 / 81

Poggibonsi House - 6.4 miles away

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

Responds fast! Avg. 2 hours 38 minutes

$717.00

Book

from $717.00 / night

1 / 20

Monteriggioni House - 6.4 miles away

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

$234.00

Inquire

from $234.00 / night

1 / 25

San Donato in Poggio Apartment - 4.8 miles away

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

$239.00

Inquire

from $239.00 / night

1 / 27

San Donato in Poggio Apartment - 4.8 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$247.00

Inquire

from $247.00 / night

1 / 42

Castelnuovo Berardenga Villa - 12.5 miles away

  • 5
  • 10
  • 7 nights min
  • Child friendly

$1,304.00

Inquire

from $1,304.00 / night

1 / 28

San Gimignano Villa - 11.7 miles away

  • 3
  • 6
  • 7 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly

$231.00

Inquire

from $231.00 / night

1 / 34

Radda in Chianti Villa - 6.4 miles away

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

$226.00

Book

from $226.00 / night

1 / 33

Tavarnelle Val di Pesa Apartment - 8.4 miles away

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

$112.00

Inquire

from $112.00 / night

1 / 28

San Donato in Poggio Apartment - 4.8 miles away

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

$260.00

Inquire

from $260.00 / night

1 / 66

Montespertoli Villa - 14.2 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$414.00

Book

from $414.00 / night

1 / 20

Montebenichi House - 13.8 miles away

  • 11
  • 22
  • 7 nights min
  • Ask about children
  • Pet friendly

$1,296.00

Inquire

from $1,296.00 / night

1 / 60

Bucine Villa - 17 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$407.00

Book

from $407.00 / night

1 / 108

Certaldo Villa - 14.8 miles away

  • 9
  • 19
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$553.00

Inquire

from $553.00 / night

1 / 33

San Donato in Poggio Apartment - 4.8 miles away

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

$198.00

Inquire

from $198.00 / night

1 / 40

San Casciano in Val di Pesa Villa - 10.9 miles away

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

$1,327.00

Inquire

from $1,327.00 / night

1 / 14

Tavarnelle Val di Pesa Apartment - 8.4 miles away

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$111.00

Inquire

from $111.00 / night