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Holiday Lettings
> Europe
> Italy
> Tuscany
> Province of Siena
> San Gimignano
> Villas and Apartments in Castel San Gimignano

Holiday Rentals in Castel San Gimignano - Holiday Lettings - Villas

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£1 £750 -

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  • Apartment (3)
  • Villa (10)
  • Castle (1)
  • Farmhouse (3)

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17 Holiday homes

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Games room
Horse riding

Great rentals within 20 miles that match your search

Holiday villa accommodation

San Casciano in Val di Pesa villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 15

from £1,380 / night

£8,767 - £10,347 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday villa rental

Tavarnelle Val di Pesa villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 20

from £1,353 / night

£9,470 / week

1 / 102

Great rentals within 20 miles that match your search

Apartment rental in Casole d'Elsa with shared pool

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £986 / night

£6,896 / week

1 / 7

Great rentals within 20 miles that match your search

Villa rental in Tavarnelle Val di Pesa with swimming pool

Tavarnelle Val di Pesa villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 20
1 review

from £1,353 / night

£9,470 / week

1 / 101

Great rentals within 20 miles that match your search

Holiday farmhouse with shared pool in Colle di Val d'Elsa

Colle di Val d'Elsa farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Pricing unknown

1 / 17

Great rentals within 20 miles that match your search

Casole d'Elsa holiday apartment let

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £986 / night

£6,898 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Mura,Italy

Mura,Italy villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from £552 / night

£3,498 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday villa accommodation

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £1,268 / night

£8,870 / week

1 / 56

Great rentals within 20 miles that match your search

Holiday villa accommodation

Radicondoli villa

  • 12 bedrooms
  • 14 bathrooms
  • sleeps 36
20 reviews

from £1,577 / night

£9,361 - £11,775 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday farmhouse rental

Montespertoli farmhouse

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 8
5 reviews

from £986 / night

£6,898 / week

1 / 27

Great rentals within 20 miles that match your search

Florence holiday villa rental

Florence villa

  • 18 bedrooms
  • 16 bathrooms
  • sleeps 40
12 reviews

from £2,956 / night

£20,693 / week

1 / 122

Great rentals within 20 miles that match your search

Holiday apartment in Monteguidi

Monteguidi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
1 review

from £71 / night

£493 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday farmhouse in Castelfiorentino

Castelfiorentino farmhouse

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 20
2 reviews

from £1,281 / night

£4,035 - £6,794 / week

1 / 12

Great rentals within 20 miles that match your search

Villa rental in Siena with swimming pool

Siena villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16
4 reviews

from £887 / night

£6,207 / week

1 / 51

Great rentals within 20 miles that match your search

Holiday villa rental

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14
28 reviews

from £1,689 / night

£11,822 - £14,678 / week

1 / 61

Great rentals within 20 miles that match your search

Castelfiorentino holiday castle rental

Castelfiorentino castle

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12
9 reviews

from £1,123 / night

£7,862 - £9,704 / week

1 / 52

Great rentals within 20 miles that match your search

Holiday villa in Barberino Val d'Elsa

Barberino Val d'Elsa villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8
2 reviews

from £375 / night

£2,621 / week

1 / 71

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Apartment rental in Montaione with shared pool

Montaione apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 filter does not match: Games room

from £222 / night

£1,634 - £2,952 / week

1 / 24

Great rentals within 20 miles that match your search

Montaione holiday apartment rental

Montaione apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Games room

from £204 / night

£1,424 - £1,993 / week

1 / 24

Great rentals within 20 miles that match your search

Apartment rental in Montaione with shared pool

Montaione apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 filter does not match: Games room

from £254 / night

£1,775 - £2,958 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Montecastelli Pisano

Montecastelli Pisano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Games room

from £69 / night

£483 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday apartment rental

Colle di Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Games room

1 review

from £99 / night

£690 - £1,114 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Games room

from £99 / night

£690 - £1,114 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Games room

from £99 / night

£690 - £1,114 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Colle di Val d'Elsa

Colle di Val d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Games room

from £76 / night

£532 - £887 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Games room

from £99 / night

£690 - £1,114 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Games room

from £76 / night

£532 - £887 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Games room

from £99 / night

£690 - £1,114 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Games room

from £127 / night

£887 - £1,478 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday apartment rental

Colle di Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Games room

from £127 / night

£887 - £1,587 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Montespertoli

Montespertoli apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Games room

from £197 / night

£1,015 - £1,291 / week

1 / 28

Great rentals within 20 miles that match your search

Apartment rental in Montespertoli with shared pool

Montespertoli apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Games room

from £138 / night

£700 - £1,065 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday townhouse with shared pool in Tavarnelle Val di Pesa

Tavarnelle Val di Pesa townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Games room

8 reviews

from £89 / night

£621 / week

1 / 58

Great rentals within 20 miles that match your search

Holiday home with shared pool in San Casciano in Val di Pesa

San Casciano in Val di Pesa house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Games room

from £207 / night

£1,449 / week

1 / 13

Great rentals within 20 miles that match your search

San Casciano in Val di Pesa holiday farmhouse rental

San Casciano in Val di Pesa farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Games room

2 reviews

from £291 / night

£2,035 / week

1 / 23

Great rentals within 20 miles that match your search

Casole d'Elsa holiday apartment rental

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Games room

from £207 / night

£1,370 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday farmhouse rental

Barberino Val d'Elsa farmhouse

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Games room

from £434 / night

£2,661 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday villa in Altopascio

Altopascio villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Horse riding

from £113 / night

£630 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Casole d'Elsa

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Horse riding

from £986 / night

£6,898 / week

1 / 9

Great rentals within 20 miles that match your search

Casole d'Elsa holiday apartment rental

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Horse riding

from £986 / night

£6,898 / week

1 / 16

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