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Holiday Lettings
> Europe
> Italy
> Tuscany
> Province of Siena
> Apartments and Villas in Gaiole in Chianti

Holiday Rentals in Gaiole in Chianti - Holiday Lettings - Villas

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  • Cottage (18)
  • Apartment (276)
  • Villa (170)
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  • Penthouse (1)
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  • Barn (5)
  • Castle (2)
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  • Farmhouse (76)
  • Studio (8)
  • Finca (4)
  • Condo (3)
  • Tower (1)
  • Private room (2)
  • Hotel apartment (12)
  • Guest house (4)
  • B&B (26)

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18 Holiday homes

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Great rentals within 20 miles that match your search

Holiday cottage with shared pool in Rapale

Rapale cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £296 / night

£2,068 / week

1 / 21

Great rentals within 20 miles that match your search

Greve in Chianti holiday cottage rental

Greve in Chianti cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £56 / night

£355 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday cottage in Pieve di Panzano

Pieve di Panzano cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £157 / night

£1,096 / week

1 / 38

Great rentals within 20 miles that match your search

Cottage accommodation in Pieve di Panzano

Pieve di Panzano cottage

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

from £295 / night

£2,061 / week

1 / 38

Great rentals within 20 miles that match your search

San Donato in Poggio holiday cottage rental

San Donato in Poggio cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £105 / night

£731 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday cottage in Rapolano Terme

Rapolano Terme cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 5
19 reviews

from £78 / night

£394 - £808 / week

1 / 58

Great rentals within 20 miles that match your search

Holiday cottage with swimming pool in San Leolino

San Leolino cottage

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £350 / night

£2,068 - £2,954 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday cottage with shared pool in Castellina In Chianti

Castellina In Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £148 / night

£901 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday cottage in San Casciano in Val di Pesa

San Casciano in Val di Pesa cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £89 / night

£572 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday cottage with swimming pool in Armaiolo

Armaiolo cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £114 / night

£766 - £1,463 / week

1 / 66

Great rentals within 20 miles that match your search

Holiday cottage with swimming pool in Radda in Chianti

Radda in Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2
28 reviews

from £266 / night

£1,861 / week

1 / 21

Great rentals within 20 miles that match your search

Cottage rental in San Donato in Poggio

San Donato in Poggio cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £218 / night

£1,524 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday cottage with shared pool in Castellina In Chianti

Castellina In Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2
46 reviews

from £148 / night

£901 - £1,212 / week

1 / 31

Great rentals within 20 miles that match your search

Cottage rental in Castellina In Chianti with shared pool

Castellina In Chianti cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £234 / night

£1,519 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday cottage with swimming pool in Armaiolo

Armaiolo cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £111 / night

£766 - £1,463 / week

1 / 64

Great rentals within 20 miles that match your search

Holiday cottage with shared pool in Pergine Valdarno

Pergine Valdarno cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10
11 reviews

from £444 / night

£3,102 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday cottage in Montebenichi

Montebenichi cottage

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

from £724 / night

£5,066 - £7,560 / week

1 / 51

Great rentals within 20 miles that match your search

Holiday cottage in Castellina In Chianti

Castellina In Chianti cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4
8 reviews

from £158 / night

£1,103 / week

1 / 48

Great rentals within 20 miles that match your search

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Cavriglia holiday apartment rental

Cavriglia apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Property type

from £187 / night

£1,303 / week

1 / 23

Great rentals within 20 miles that match your search

Apartment rental in Vagliagli

Vagliagli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £69 / night

£483 / week

1 / 4

Great rentals within 20 miles that match your search

Apartment rental in Greve in Chianti

Greve in Chianti apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 filter does not match: Property type

from £296 / night

£1,773 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Property type

1 review

from £197 / night

£1,379 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday apartment in Costalpino

Costalpino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £69 / night

£444 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday apartment rental

Torre A Castello apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Property type

12 reviews

from £55 / night

£380 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday apartment in Greve in Chianti

Greve in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £119 / night

£690 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in San Felice

San Felice apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Property type

from £155 / night

£1,084 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday b&b in Siena

Siena b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

2 reviews

from £165 / night

£1,152 / week

1 / 11

Great rentals within 20 miles that match your search

B&b accommodation in Siena

Siena b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £127 / night

£890 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday apartment in San Donato in Poggio

San Donato in Poggio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £98 / night

£683 / week

1 / 525

Great rentals within 20 miles that match your search

Holiday apartment in Nusenna

Nusenna apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £178 / night

£1,241 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday farmhouse in Siena

Siena farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £305 / night

£2,130 / week

1 / 44

Great rentals within 20 miles that match your search

Holiday home in Monteriggioni

Monteriggioni house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Property type

1 review

from £74 / night

£517 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday farmhouse in Siena

Siena farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £206 / night

£1,441 / week

1 / 43

Great rentals within 20 miles that match your search

Apartment rental in Siena

Siena apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

1 filter does not match: Property type

10 reviews

from £84 / night

£586 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday apartment rental

Panzano in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £49 / night

£338 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £148 / night

£1,034 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday b&b in Siena

Siena b&b

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £197 / night

£1,379 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday apartment in Montaperti

Montaperti apartment

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

1 filter does not match: Property type

2 reviews

from £325 / night

£2,275 / week

1 / 28

Great rentals within 20 miles that match your search

Radda in Chianti holiday guest house rental

Radda in Chianti guest house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 filter does not match: Property type

Pricing unknown

1 / 11

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Terranuova Bracciolini

Terranuova Bracciolini apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 7

1 filter does not match: Property type

from £109 / night

£591 / week

1 / 14

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