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Apartments in Castel San Gimignano and Houses – Holiday Lettings - Holiday Rentals Castel San Gimignano

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2,858 Holiday homes

Holiday cottage in Castel San Gimignano

Castel San Gimignano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £73 / night

£508 / week

1 / 28

Holiday apartment with swimming pool, golf nearby in Castel San Gimignano

Castel San Gimignano apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 22

from £804 / night

£6,193 / week

1 / 19

Holiday home with swimming pool in Castel San Gimignano

Castel San Gimignano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £268 / night

£1,545 - £2,820 / week

1 / 35

Holiday home with swimming pool in Castel San Gimignano

Castel San Gimignano house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £63 / night

£445 - £1,003 / week

1 / 45

Castel San Gimignano holiday apartment rental

Castel San Gimignano apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £97 / night

£630 - £823 / week

1 / 43

Holiday home with swimming pool in Castel San Gimignano

Castel San Gimignano house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £177 / night

£1,238 / week

1 / 44

Holiday b&b in Castel San Gimignano

Castel San Gimignano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £87 / night

£610 / week

1 / 78

Farmhouse rental in Castel San Gimignano with shared pool, golf nearby

Castel San Gimignano farmhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

from £242 / night

£1,694 / week

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Holiday villa in Castel San Gimignano

Castel San Gimignano villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £398 / night

£796 / week

1 / 42

Holiday home with swimming pool in Castel San Gimignano

Castel San Gimignano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £132 / night

£924 - £2,178 / week

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Castel San Gimignano holiday villa rental

Castel San Gimignano villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £171 / night

£1,191 - £2,479 / week

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Farmhouse rental in Castel San Gimignano with shared pool

Castel San Gimignano farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £242 / night

£1,694 / week

1 / 39

Castel San Gimignano holiday apartment rental

Castel San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £97 / night

£630 - £824 / week

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Castel San Gimignano holiday apartment rental

Castel San Gimignano apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £97 / night

£630 - £823 / week

1 / 14

Farmhouse rental in Castel San Gimignano with shared pool, golf nearby

Castel San Gimignano farmhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

from £242 / night

£1,694 / week

1 / 57

Great rentals within 20 miles that match your search

Holiday b&b in Colle di Val d'Elsa

Colle di Val d'Elsa b&b

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

from £63 / night

£407 - £1,762 / week

1 / 33

Holiday apartment with shared pool in Barberino Val d'Elsa

Barberino Val d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £189 / night

£1,258 / week

1 / 30

Holiday b&b in Montaione

Montaione b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £83 / night

£407 - £813 / week

1 / 34

Holiday b&b rental

Certaldo b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

from £34 / night

£237 - £339 / week

1 / 47

Holiday home in Castelnuovo Berardenga

Castelnuovo Berardenga house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £83 / night

£581 / week

1 / 12

Holiday apartment with shared pool in Barberino Val d'Elsa

Barberino Val d'Elsa apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

from £226 / night

£1,500 / week

1 / 34

Holiday b&b rental

Tuscany b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £63 / night

£441 - £542 / week

1 / 4

Holiday apartment in Montescudaio

Montescudaio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £78 / night

£484 - £1,500 / week

1 / 13

San Casciano in Val di Pesa holiday home rental

San Casciano in Val di Pesa house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £117 / night

£775 / week

1 / 90

Holiday apartment in Certaldo

Certaldo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £90 / night

£629 / week

1 / 8

San Miniato holiday apartment rental

San Miniato apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £78 / night

£504 / week

1 / 3

Holiday cottage with swimming pool in Radda in Chianti

Radda in Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £223 / night

£1,558 / week

1 / 20

Colle di Val d'Elsa holiday apartment rental

Colle di Val d'Elsa apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 5

from £276 / night

£1,936 / week

1 / 24

Holiday apartment rental

Castellina In Chianti apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

from £235 / night

£1,645 - £2,439 / week

1 / 17

San Casciano in Val di Pesa holiday farmhouse rental

San Casciano in Val di Pesa farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £62 / night

£354 / week

1 / 22

Castellina In Chianti holiday b&b rental

Castellina In Chianti b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £105 / night

£736 - £1,152 / week

1 / 22

Holiday cottage with shared pool in Castellina In Chianti

Castellina In Chianti cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £213 / night

£1,123 - £1,636 / week

1 / 30

B&b rental in Castellina In Chianti with shared pool

Castellina In Chianti b&b

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £262 / night

£1,568 - £2,197 / week

1 / 30

Castellina In Chianti holiday farmhouse rental

Castellina In Chianti farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £155 / night

£833 - £1,200 / week

1 / 25

Villa rental in Siena with shared pool

Siena villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 13

from £407 / night

£1,887 - £3,455 / week

1 / 36

Holiday villa in Gambassi Terme

Gambassi Terme villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £204 / night

£1,423 / week

1 / 55

Holiday home with shared pool in San Gimignano

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £70 / night

£484 / week

1 / 10

Holiday home rental

Volterra house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £57 / night

£400 - £468 / week

1 / 27

Holiday villa in Siena

Siena villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £126 / night

£628 - £1,674 / week

1 / 41

Apartment rental in Polvereto with shared pool

Polvereto apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Pricing unknown

1 / 6

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Top Destination reviews

Casa Gelsomino, ground floor, 2 bedrooms, private garden and shared pool
Great apartment. Fantastic Tuscan hospitality.

My wife and I chose Casa Gelsomino because we were travelling with our 18-month old daughter and wanted to be in a location with amenities within walking distance. The hamlet of Castel San Gimignano itself is a sleepy one but offers a great little convenience store (run by twin sisters) just across the road from the apartment, a nice bar (opposite) and a lovely restaurant offering a variety of Tuscan/Italian cuisine. As for the apartment, located on the ground floor (we were able to park our car directly outside the front door) with a spacious lounge diner and a compact but well-equipped kitchen neatly tucked away behind double sliding doors. Beyond that, a utility room with a washing machine, a decent family bathroom (shower cubicle but no bathtub) and two bedrooms; one with a king size bed the other with a day bed that converts into two singles or a double. We used this room for our daughter and Carlo (owner) provided a travel cot and bedding as well as a highchair. Free wifi was provided also offering speeds of around 12Mbps download and around 1 Mbps upload. Not bad considering it's in such a rural setting. By far the biggest positive for us was the outdoor space. Beautifully manicured lawns and flowerbeds leading down to the private pool and then the olive groves and cherry orchards beyond, all expertly and meticulously tended to by Carlo's mother Anna and father Renzo. It has to be said at this point that these lovely people were so warm and friendly and couldn't do enough to make our stay as comfortable and relaxing as possible. Anna even went as far as picking fresh herbs for me to use in my ragu and Renzo picked a load of cherries for us also. Whilst the pool was spotlessly clean (maintained by Carlo daily) it isn't heated, and whilst it was bearable for us adults, it was a little too cold for our daughter despite the ambient temperature being in the mid-30's centigrade. Plenty of sun loungers and the views across the valley are spectacular, particularly at sundown enjoying a glass or two of Chianti. All in all, we had a most enjoyable week here whilst exploring the surrounding areas including Siena, San Gimignano and Volterra to name a few. A car is recommended if staying for longer than a few days. One recommendation I would make, is for a welcome pack to be offered (even at a small charge) including basic sundries like salt, pepper, sugar, olive oil, milk etc. as the last thing you want to do after a long journey is then thinking about going to the supermarket, especially with a toddler :-) In summary, the apartment was great but the hospitality was superb! Tantissimi grazie Carlo, Emanuela, Anna e Renzo!see more
Casa Verbena, 3 bedrooms apartment, first floor, terrace
Perfect location with delightful owners

This is such a beautiful spot and ideal for exploring as very close to everything we wanted to see: Siena, San Gimignano, Volterra and many other less well known medieval towns and villages. The pool has a stunning view and is a perfect place to sunbathe, relax and read as well as cool off after a day's sightseeing. The owners couldn't have been more welcoming and their parents, who live on site, are completely charming. They brought us plums from their orchard and tried to help with our hopeless Italian. The only thing we missed in our upstairs, sleeps 6, appt was the opportunity to eat outside. To be fair, there is an outside eating area by the pool which we were told we could use but we felt uncomfortable about this as it belonged to the owners parents. That, however, is probably the fault of our own English reserve but it is the reason why I have given this a rating of 'Very Good' rather than 'Excellent'. The appartment was very comfortable, the location ideal for exploring and the owners completely charming and helpful.see more

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