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Holiday Rentals in Castel San Gimignano - Holiday Lettings - Villas

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20 Holiday homes

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Great rentals within 20 miles that match your search

Holiday villa rental

Montespertoli villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £415 / night

£2,903 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Montaione

Montaione villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 22

from £791 / night

£4,772 - £10,166 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Montaione

Montaione villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £672 / night

£4,073 - £7,530 / week

1 / 47

Great rentals within 20 miles that match your search

Holiday villa in Certaldo

Certaldo villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 18

from £458 / night

£3,205 / week

1 / 110

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Montespertoli

Montespertoli villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £175 / night

£1,223 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday villa rental

Montaione villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

from £667 / night

£3,957 - £9,789 / week

1 / 58

Great rentals within 20 miles that match your search

Holiday villa in Castelfiorentino

Castelfiorentino villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £284 / night

£1,986 / week

1 / 26

Great rentals within 20 miles that match your search

Certaldo holiday villa rental

Certaldo villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 19

from £458 / night

£3,205 / week

1 / 108

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Barberino Val d'Elsa

Barberino Val d'Elsa house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

from £440 / night

£2,492 - £5,477 / week

1 / 46

Great rentals within 20 miles that match your search

Apartment rental in Montaione with shared pool

Montaione apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £221 / night

£1,564 - £2,939 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Montaione

Montaione villa

  • 17 bedrooms
  • 14 bathrooms
  • sleeps 29

from £1,148 / night

£7,174 - £12,514 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday villa in Certaldo

Certaldo villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 18

from £509 / night

£3,521 - £9,584 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday villa accommodation

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £1,258 / night

£8,804 / week

1 / 56

Great rentals within 20 miles that match your search

Holiday villa in Montelupo Fiorentino

Montelupo Fiorentino villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 17

from £274 / night

£1,810 - £3,423 / week

1 / 24

Great rentals within 20 miles that match your search

Florence holiday villa rental

Florence villa

  • 18 bedrooms
  • 16 bathrooms
  • sleeps 40

from £2,934 / night

£20,537 / week

1 / 122

Great rentals within 20 miles that match your search

Holiday apartment in Poggibonsi

Poggibonsi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

from £152 / night

£1,061 - £2,978 / week

1 / 43

Great rentals within 20 miles that match your search

Siena holiday villa rental

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

from £98 / night

£685 - £2,328 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday villa rental

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

from £1,677 / night

£11,735 - £14,571 / week

1 / 61

Great rentals within 20 miles that match your search

Montaione holiday apartment rental

Montaione apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £203 / night

£1,416 - £1,983 / 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

from £252 / night

£1,762 - £2,936 / week

1 / 31

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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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: Heated pool

from £69 / night

£480 / week

1 / 32

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: Heated pool

from £196 / night

£1,008 - £1,281 / 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: Heated pool

from £137 / night

£695 - £1,057 / week

1 / 23

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: Heated pool

from £206 / night

£1,438 / 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: Heated pool

from £289 / night

£2,020 / 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: Heated pool

from £98 / night

£685 - £1,105 / 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: Heated pool

from £98 / night

£685 - £1,105 / 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: Heated pool

from £98 / night

£685 - £1,105 / 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: Heated pool

from £98 / night

£685 - £1,105 / week

1 / 22

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: Heated pool

from £76 / night

£528 - £881 / 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: Heated pool

from £98 / night

£685 - £1,105 / 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: Heated pool

from £76 / night

£528 - £881 / 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

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Heated pool

from £126 / night

£881 - £1,467 / 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: Heated pool

from £126 / night

£881 - £1,575 / week

1 / 23

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: Heated pool

from £431 / night

£2,641 / week

1 / 12

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: Heated pool

from £88 / night

£616 / week

1 / 58

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: Heated pool

from £206 / night

£1,360 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday villa in Tavarnelle Val di Pesa

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

1 filter does not match: Horse riding

from £1,328 / night

£9,291 / week

1 / 52

Great rentals within 20 miles that match your search

Villa rental in Montespertoli

Montespertoli villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 filter does not match: Horse riding

from £415 / night

£2,903 / week

1 / 32

Great rentals within 20 miles that match your search

Home rental in Montaione

Montaione house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

1 filter does not match: Horse riding

from £628 / night

£4,396 / week

1 / 74

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