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Holiday Lettings
> Europe
> Italy
> Tuscany
> Province of Siena
> San Gimignano
> Castel San Gimignano
> City Breaks & Holidays

Castel San Gimignano Holidays & City Breaks - Holiday Lettings

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227 properties suitable for city breaks and holidays

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City breaks

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Certaldo Alto

Certaldo Alto apartment

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

from £573 / night

£4,008 / week

1 / 11

Great rentals within 20 miles that match your search

Certaldo holiday apartment rental

Certaldo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £98 / night

£686 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Il Pino

Il Pino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £701 / night

£4,898 / week

1 / 10

Great rentals within 20 miles that match your search

Montelupo Fiorentino holiday apartment rental

Montelupo Fiorentino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
1 review

from £79 / night

£549 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Il Pino

Il Pino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from £378 / night

£2,645 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday apartment in Il Pino

Il Pino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £742 / night

£5,193 / week

1 / 8

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 £1,228 / night

£5,893 - £9,744 / week

1 / 233

Great rentals within 20 miles that match your search

Empoli holiday home rental

Empoli house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from £103 / night

£588 - £835 / week

1 / 21

Great rentals within 20 miles that match your search

Apartment rental in Certaldo with shared pool

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £140 / night

£980 / week

1 / 5

Great rentals within 20 miles that match your search

Holiday apartment in Certaldo

Certaldo apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £197 / night

£1,374 / week

1 / 5

Great rentals within 20 miles that match your search

Holiday apartment in Radicondoli

Radicondoli apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £84 / night

£412 / week

1 / 17

Great rentals within 20 miles that match your search

Certaldo holiday villa rental

Certaldo villa

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 15

from £1,861 / night

£13,027 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday apartment in Certaldo Alto

Certaldo Alto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £115 / night

£802 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday apartment in Certaldo

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £123 / night

£859 / week

1 / 5

Great rentals within 20 miles that match your search

Apartment rental in San Gimignano

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
14 reviews

from £98 / night

£588 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday guest house with golf nearby in San Gimignano

San Gimignano guest house

  • 10 bedrooms
  • 5 bathrooms
  • sleeps 20

from £676 / night

£4,408 - £6,053 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday apartment in Certaldo

Certaldo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £82 / night

£573 / week

1 / 3

Great rentals within 20 miles that match your search

Holiday apartment in Certaldo Alto

Certaldo Alto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £98 / night

£686 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Montaione

Montaione apartment

  • 24 bedrooms
  • 1 bathroom
  • sleeps 6

from £65 / night

£588 / week

1 / 52

Great rentals within 20 miles that match your search

Holiday farmhouse letting

Montespertoli farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Pricing unknown

1 / 17

Great rentals within 20 miles that match your search

Gambassi Terme holiday apartment rental

Gambassi Terme apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5
1 review

Pricing unknown

1 / 8

Great rentals within 20 miles that match your search

Holiday home in Scandicci

Scandicci house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £160 / night

£1,118 / week

1 / 13

Great rentals within 20 miles that match your search

Montespertoli holiday hotel apartment rental

Montespertoli hotel apartment

  • 21 bedrooms
  • 1 bathroom
  • sleeps 2
1 review

from £65 / night

£412 / week

1 / 4

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
  • 2 bathrooms
  • sleeps 4
37 reviews

from £98 / night

£108 - £657 / week

1 / 54

Great rentals within 20 miles that match your search

Montignoso holiday apartment rental

Montignoso apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Pricing unknown

1 / 14

Great rentals within 20 miles that match your search

Holiday b&b in Marcialla

Marcialla b&b

  • 7 bedrooms
  • 13 bathrooms
  • sleeps 18

from £588 / night

£4,114 / week

1 / 10

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

San Gimignano holiday guest house rental

San Gimignano guest house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

from £383 / night

£2,456 - £3,693 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday apartment rental

Il Pino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £378 / night

£2,645 / week

1 / 8

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Il Pino

Il Pino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £701 / night

£4,898 / week

1 / 8

Great rentals within 20 miles that match your search

Home rental in San Gimignano

San Gimignano house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £68 / night

£382 / week

1 / 47

Great rentals within 20 miles that match your search

Holiday apartment in Poggibonsi

Poggibonsi apartment

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 5

from £91 / night

£588 / week

1 / 8

Great rentals within 20 miles that match your search

Scandicci holiday b&b rental

Scandicci b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £49 / night

£343 / week

1 / 7

Great rentals within 20 miles that match your search

Holiday home rental

Radicondoli house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6
2 reviews

from £235 / night

£1,646 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday apartment in Ginestra Fiorentina

Ginestra Fiorentina apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £118 / night

£825 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday apartment in San Gimignano

San Gimignano apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £108 / night

£637 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday tower rental

Monticiano tower

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

from £89 / night

£588 - £1,102 / week

1 / 24

Great rentals within 20 miles that match your search

Casole d'Elsa holiday townhouse rental

Casole d'Elsa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £49 / night

£343 / week

1 / 7

Great rentals within 20 miles that match your search

Holiday apartment in Scandicci

Scandicci apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £107 / night

£748 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday apartment in Certaldo Alto

Certaldo Alto apartment

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Pricing unknown

1 / 10

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