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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 (17)
  • Apartment (186)
  • Villa (146)
  • House (100)
  • Penthouse (1)
  • Lodge (1)
  • Manor House (1)
  • Barn (5)
  • Castle (2)
  • Townhouse (7)
  • Farmhouse (60)
  • Studio (5)
  • Finca (4)
  • Condo (2)
  • B&B (12)
  • Hotel apartment (9)
  • Guest house (2)

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17 Holiday homes

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Cottage
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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 £55 / night

£354 / 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 £166 / night

£1,162 / 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 £320 / night

£2,235 / week

1 / 38

Great rentals within 20 miles that match your search

Campoli in Chianti holiday cottage rental

Campoli in Chianti cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6
1 review

from £128 / night

£855 / week

1 / 57

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 £349 / night

£2,063 - £2,947 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday cottage in Levane

Levane cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £261 / night

£1,822 / week

1 / 27

Great rentals within 20 miles that match your search

Cottage rental in Monteriggioni

Monteriggioni cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5
3 reviews

from £89 / night

£492 / week

1 / 28

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

£570 / week

1 / 20

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 £104 / night

£722 - £894 / week

1 / 19

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 £113 / night

£765 - £1,459 / week

1 / 66

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 £203 / night

£1,417 / 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

£899 - £1,209 / 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 £233 / night

£1,515 / 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 £110 / night

£765 - £1,459 / 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 £442 / night

£3,094 / 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 £722 / night

£5,053 - £7,541 / 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

£1,100 / week

1 / 48

Great rentals within 20 miles that match your search

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Colonna di Grillo holiday apartment rental

Colonna di Grillo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 filter does not match: Property type

from £69 / night

£482 / week

1 / 16

Great rentals within 20 miles that match your search

Colonna di Grillo holiday apartment rental

Colonna di Grillo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £73 / night

£509 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday apartment in Barberino Val d'Elsa

Barberino Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Property type

from £174 / night

£1,217 / week

1 / 7

Great rentals within 20 miles that match your search

Holiday apartment in Pianella

Pianella apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £141 / night

£984 / week

1 / 29

Great rentals within 20 miles that match your search

Villa rental in Rapolano Terme

Rapolano Terme villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 filter does not match: Property type

1 review

from £99 / night

£688 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday studio in Greve in Chianti

Greve in Chianti studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 filter does not match: Property type

3 reviews

Pricing unknown

1 / 10

Great rentals within 20 miles that match your search

Holiday apartment in San Rocco a Pilli

San Rocco a Pilli apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £158 / night

£1,100 / week

1 / 7

Great rentals within 20 miles that match your search

Apartment rental in Castelnuovo Berardenga

Castelnuovo Berardenga apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £61 / night

£427 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday hotel apartment rental

Greve in Chianti hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £177 / night

£1,238 / week

1 / 69

Great rentals within 20 miles that match your search

Holiday hotel apartment with shared pool in Greve in Chianti

Greve in Chianti hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £177 / night

£1,238 / week

1 / 71

Great rentals within 20 miles that match your search

Holiday hotel apartment with shared pool in Greve in Chianti

Greve in Chianti hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £177 / night

£1,238 / week

1 / 76

Great rentals within 20 miles that match your search

Holiday hotel apartment rental

Greve in Chianti hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £177 / night

£1,238 / week

1 / 71

Great rentals within 20 miles that match your search

Pietraviva holiday farmhouse rental

Pietraviva farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £156 / night

£980 - £1,165 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday farmhouse in Pietraviva

Pietraviva farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £156 / night

£980 - £1,165 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday farmhouse in Pietraviva

Pietraviva farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £156 / night

£980 - £1,165 / week

1 / 15

Great rentals within 20 miles that match your search

Greve in Chianti holiday b&b rental

Greve in Chianti b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £108 / night

£737 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday apartment in Caprera

Caprera apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £118 / night

£825 / week

1 / 34

Great rentals within 20 miles that match your search

Holiday apartment with golf nearby in San Rocco a Pilli

San Rocco a Pilli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £138 / night

£963 / week

1 / 11

Great rentals within 20 miles that match your search

Siena holiday finca rental

Siena finca

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £158 / night

£1,100 / week

1 / 5

Great rentals within 20 miles that match your search

Holiday farmhouse with shared pool in Siena

Siena farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £99 / night

£688 / week

1 / 8

Great rentals within 20 miles that match your search

Castellina In Chianti holiday apartment rental

Castellina In Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £93 / night

£1,066 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Vagliagli

Vagliagli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

1 review

from £62 / night

£334 - £472 / week

1 / 40

Great rentals within 20 miles that match your search

Greve in Chianti holiday apartment rental

Greve in Chianti apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

1 review

from £99 / night

£688 / week

1 / 13

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