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

Holiday Rentals in Castel San Gimignano - Holiday Lettings - Villas

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£1 £750 -

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  • Apartment (20)
  • Villa (6)
  • Cottage (2)
  • House (1)
  • Barn (1)
  • Farmhouse (3)
  • Private room (1)
  • B&B (1)

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35 Holiday homes

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Ceiling Fans
Horse riding

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Siena

Siena villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

from £1,227 / night

£5,889 - £9,737 / week

1 / 233

Great rentals within 20 miles that match your search

San Gimignano holiday apartment rental

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
3 reviews

from £69 / night

£501 - £666 / week

1 / 63

Great rentals within 20 miles that match your search

Holiday b&b rental

Certaldo b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

from £35 / night

£241 - £344 / week

1 / 47

Great rentals within 20 miles that match your search

Holiday private room with shared pool in San Gimignano

San Gimignano private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £175 / night

£1,224 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday villa rental

Cerbaia villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16
7 reviews

from £884 / night

£6,184 / week

1 / 40

Great rentals within 20 miles that match your search

Holiday barn with swimming pool, golf nearby in Montelupo Fiorentino

Montelupo Fiorentino barn

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £246 / night

£2,652 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday apartment in Montagnana Val di Pesa

Montagnana Val di Pesa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £148 / night

£983 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday farmhouse in Radicondoli

Radicondoli farmhouse

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

from £344 / night

£2,407 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Montecastelli Pisano

Montecastelli Pisano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £104 / night

£688 / week

1 / 36

Great rentals within 20 miles that match your search

San Casciano in Val di Pesa holiday villa rental

San Casciano in Val di Pesa villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11
4 reviews

from £562 / night

£3,929 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday farmhouse in Radicondoli

Radicondoli farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £246 / night

£1,375 - £2,750 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday farmhouse with shared pool in San Gimignano

San Gimignano farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5
30 reviews

from £113 / night

£791 / week

1 / 35

Great rentals within 20 miles that match your search

Montecastelli Pisano holiday apartment rental

Montecastelli Pisano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £74 / night

£491 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Montecastelli Pisano

Montecastelli Pisano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £94 / night

£619 / week

1 / 38

Great rentals within 20 miles that match your search

Montespertoli holiday apartment rental

Montespertoli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £76 / night

£529 / week

1 / 12

Great rentals within 20 miles that match your search

Apartment letting in Montespertoli with shared pool

Montespertoli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £138 / night

£983 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Montespertoli

Montespertoli apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £295 / night

£1,670 / week

1 / 14

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

from £74 / night

£491 / week

1 / 34

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

from £79 / night

£521 / week

1 / 36

Great rentals within 20 miles that match your search

Apartment letting in Montecastelli Pisano with shared pool

Montecastelli Pisano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £79 / night

£523 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Montecastelli Pisano

Montecastelli Pisano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £84 / night

£555 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday apartment rental

Castelfiorentino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7
5 reviews

from £113 / night

£711 - £1,682 / week

1 / 21

Great rentals within 20 miles that match your search

Apartment letting in Montespertoli with shared pool

Montespertoli apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £101 / night

£729 / week

1 / 12

Great rentals within 20 miles that match your search

Montespertoli holiday apartment rental

Montespertoli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £295 / night

£1,670 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday apartment rental

Certaldo Alto apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
10 reviews

from £74 / night

£491 - £913 / week

1 / 88

Great rentals within 20 miles that match your search

Apartment rental in Montagnana Val di Pesa with shared pool, golf nearby

Montagnana Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2
1 review

from £118 / night

£835 / week

1 / 15

Great rentals within 20 miles that match your search

Villa rental in Montelupo Fiorentino with swimming pool

Montelupo Fiorentino villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 11
1 review

from £429 / night

£3,003 / week

1 / 27

Great rentals within 20 miles that match your search

Apartment rental in San Gimignano

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3
2 reviews

from £82 / night

£547 / week

1 / 64

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

£491 / week

1 / 28

Great rentals within 20 miles that match your search

Radicondoli holiday home rental

Radicondoli house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
1 review

from £79 / night

£550 / week

1 / 51

Great rentals within 20 miles that match your search

Holiday cottage with swimming pool, golf nearby in Casole d'Elsa

Casole d'Elsa cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6
18 reviews

from £183 / night

£1,277 / week

1 / 24

Great rentals within 20 miles that match your search

Castelfiorentino holiday apartment rental

Castelfiorentino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7
10 reviews

from £115 / night

£724 - £1,855 / week

1 / 23

Great rentals within 20 miles that match your search

Cottage rental in Monteguidi with swimming pool

Monteguidi cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
23 reviews

from £197 / night

£1,375 / week

1 / 29

Great rentals within 20 miles that match your search

Siena holiday villa rental

Siena villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5
13 reviews

from £105 / night

£736 - £1,925 / week

1 / 23

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 £1,684 / night

£11,786 - £14,635 / week

1 / 61

Great rentals within 20 miles that match your search

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Holiday apartment with shared pool in Montecastelli Pisano

Montecastelli Pisano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Ceiling Fans

from £69 / night

£482 / week

1 / 32

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: Ceiling Fans

from £207 / night

£1,444 / 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: Ceiling Fans

2 reviews

from £290 / night

£2,029 / week

1 / 23

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: Ceiling Fans

1 review

from £99 / night

£688 - £1,110 / 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: Ceiling Fans

from £99 / night

£688 - £1,110 / week

1 / 27

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