COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Search 105,200+ Vacation Rentals

Castellina In Chianti Vacation Rentals & Homes with Swimming Pool - 157 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

157 Vacation rentals

Filters applied: Swimming pool

(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

(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

$2,229.00

Inquire

from $2,229.00 / night

Your search has been expanded 18.7 miles to include more rentals

1 / 111

Siena Villa - 10.6 miles away

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

$584.00

Inquire

from $584.00 / night

1 / 50

Tavarnelle Val di Pesa Villa - 7.9 miles away

  • 6
  • 12
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$701.00

Inquire

from $701.00 / night

1 / 34

Radda in Chianti Villa - 6.4 miles away

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

$221.00

Book

from $221.00 / 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

$1,309.00

Inquire

from $1,309.00 / night

1 / 59

Ville di Corsano Villa - 16.6 miles away

  • 9
  • 19
  • 7 nights min
  • Nearest beach 85 mi
  • Swimming pool
  • Child friendly

$1,994.00

Inquire

from $1,994.00 / night

1 / 32

Montagnana Val di Pesa Apartment - 17.5 miles away

  • 2
  • 6
  • 3 nights min
  • Nearest beach 75 mi
  • Swimming pool
  • Child friendly

$120.00

Inquire

from $120.00 / night

1 / 60

Bucine Villa - 17 miles away

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

$398.00

Book

from $398.00 / night

1 / 24

San Casciano in Val di Pesa Villa - 15.5 miles away

  • 5
  • 11
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly

$595.00

Inquire

from $595.00 / night

1 / 66

Montespertoli Villa - 14.2 miles away

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

$433.00

Book

from $433.00 / night

1 / 33

Tavarnelle Val di Pesa Apartment - 8.4 miles away

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

$119.00

Inquire

from $119.00 / night

1 / 89

Montespertoli Villa - 14.7 miles away

  • 6
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$934.00

Inquire

from $934.00 / night

1 / 36

Certaldo Villa - 13.5 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$898.00

Book

from $898.00 / 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 22 minutes

$715.00

Book

from $715.00 / night

1 / 50

Bucine Villa - 16.8 miles away

  • 9
  • 20
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 2 hours 22 minutes

$1,727.00

Book

from $1,727.00 / night

1 / 79

Tavarnelle Val di Pesa Villa - 8.1 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$1,106.00

Book

from $1,106.00 / 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 22 minutes

$580.00

Book

from $580.00 / night

1 / 33

Tavarnelle Val di Pesa Apartment - 8.4 miles away

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

$148.00

Inquire

from $148.00 / night

1 / 48

San Casciano in Val di Pesa Apartment - 12.5 miles away

  • 6
  • 26
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,328.00

Inquire

from $1,328.00 / night

1 / 14

Tavarnelle Val di Pesa Apartment - 8.4 miles away

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

$119.00

Inquire

from $119.00 / night

1 / 45

Barberino Val d'Elsa Apartment - 7.5 miles away

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$491.00

Inquire

from $491.00 / night

1 / 16

San Gimignano Villa - 14.7 miles away

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

Responds fast! Avg. 2 hours 14 minutes

$559.00

Book

from $559.00 / night

1 / 14

San Gimignano Villa - 14.6 miles away

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

Responds fast! Avg. 2 hours 14 minutes

$420.00

Book

from $420.00 / night

1 / 37

Tavarnelle Val di Pesa Apartment - 8.4 miles away

  • 2
  • 4
  • 7 nights min
  • Nearest beach 28 mi
  • Swimming pool
  • Child friendly

$117.00

Inquire

from $117.00 / night

1 / 43

Certaldo Villa - 11.7 miles away

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

$298.00

Inquire

from $298.00 / night

1 / 51

Montebenichi Cottage - 16.3 miles away

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

$749.00

Inquire

from $749.00 / night

1 / 48

Gambassi Terme Apartment - 14.9 miles away

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

$332.00

Inquire

from $332.00 / night

(2)

1 / 24

Castelfiorentino Villa - 17 miles away

  • 6
  • 12
  • min stay varies
  • Nearest beach 113 mi
  • Swimming pool
  • Child friendly

$1,090.00

Excellent (2 reviews)

Inquire

from $1,090.00 / night

1 / 60

Barberino Val d'Elsa Apartment - 7.4 miles away

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

$436.00

Inquire

from $436.00 / night

1 / 44

San Donato in Collina Villa - 18.7 miles away

  • 8
  • 16
  • 7 nights min
  • Nearest beach 130 mi
  • Swimming pool
  • Ask about children

$1,340.00

Inquire

from $1,340.00 / night

(1)

1 / 55

San Donato in Collina Villa - 18.6 miles away

  • 8
  • 15
  • 7 nights min
  • Nearest beach 130 mi
  • Swimming pool
  • Ask about children

$1,256.00

Excellent (1 reviews)

Inquire

from $1,256.00 / night

1 / 56

Barberino Val d'Elsa Apartment - 7.5 miles away

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

$314.00

Inquire

from $314.00 / night

1 / 35

Badia a Passignano Villa - 7.6 miles away

  • 8
  • 15
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$1,223.00

Book

from $1,223.00 / night

1 / 33

San Donato in Poggio Apartment - 4.8 miles away

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

$193.00

Inquire

from $193.00 / 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

$240.00

Inquire

from $240.00 / night