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Holiday homes - Holiday rentals

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243 Holiday homes

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Great rentals within 20 miles that match your search

Apartment letting in Siena

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £103 / night

£515 / week

1 / 29

Great rentals within 20 miles that match your search

Apartment rental in Barberino Val d'Elsa with swimming pool

Barberino Val d'Elsa apartment

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from £784 / night

£4,898 / week

1 / 16

Great rentals within 20 miles that match your search

Villa rental in Castelnuovo Berardenga

Castelnuovo Berardenga villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Pricing unknown

1 / 10

Great rentals within 20 miles that match your search

Holiday villa in Altopascio

Altopascio villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £113 / night

£630 / week

1 / 15

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 £1,226 / night

£5,885 - £9,730 / week

1 / 233

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Poggibonsi

Poggibonsi villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £515 / night

£5,534 / week

1 / 60

Great rentals within 20 miles that match your search

Gallena holiday home rental

Gallena house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Pricing unknown

1 / 16

Great rentals within 20 miles that match your search

Home rental in Castelnuovo Berardenga with swimming pool

Castelnuovo Berardenga house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £411 / night

£4,868 / week

1 / 32

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

from £981 / night

£6,866 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Siena

Siena house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 10

from £675 / night

£5,582 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa rental

Siena villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 17

from £1,876 / night

£13,131 / week

1 / 37

Great rentals within 20 miles that match your search

Ulignano holiday villa rental

Ulignano villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from £413 / night

£2,890 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday villa rental

Staggia Senese villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

from £484 / night

£3,384 / week

1 / 62

Great rentals within 20 miles that match your search

Radda in Chianti holiday villa rental

Radda in Chianti villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 14

from £3,825 / night

£26,775 / week

1 / 49

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Siena

Siena house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £676 / night

£5,590 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Gaiole in Chianti

Gaiole in Chianti house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £168 / night

£1,964 / week

1 / 42

Great rentals within 20 miles that match your search

Monteriggioni holiday villa rental

Monteriggioni villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £157 / night

£1,099 - £2,609 / week

1 / 108

Great rentals within 20 miles that match your search

Home rental in Castellina In Chianti with swimming pool

Castellina In Chianti house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 11

from £235 / night

£3,557 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Siena

Siena house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £553 / night

£4,291 / week

1 / 24

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 5

Pricing unknown

1 / 8

Great rentals within 20 miles that match your search

Holiday home in Colle di Val d'Elsa

Colle di Val d'Elsa house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

from £89 / night

£617 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday b&b in Siena

Siena b&b

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

from £196 / night

£1,372 / week

1 / 13

Great rentals within 20 miles that match your search

Villa rental in Castellina In Chianti with swimming pool

Castellina In Chianti villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £395 / night

£6,001 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday home in Castellina In Chianti

Castellina In Chianti house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 12

from £395 / night

£5,998 / week

1 / 58

Great rentals within 20 miles that match your search

Holiday farmhouse in Siena

Siena farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £304 / night

£2,125 / week

1 / 44

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Radda in Chianti

Radda in Chianti house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

from £410 / night

£7,065 / week

1 / 54

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Monteriggioni

Monteriggioni house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £183 / night

£2,451 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday villa in Radda in Chianti

Radda in Chianti villa

  • 5 bedrooms
  • 9 bathrooms
  • sleeps 10

from £2,194 / night

£15,355 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday villa in Sovicille

Sovicille villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £226 / night

£1,577 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday villa with shared pool in Castellina In Chianti

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

from £1,352 / night

£8,110 - £13,355 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Monteriggioni

Monteriggioni house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £212 / night

£1,483 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday home in Colle di Val d'Elsa

Colle di Val d'Elsa house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £294 / night

£2,057 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday farmhouse in Siena

Siena farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £205 / night

£1,433 / week

1 / 43

Great rentals within 20 miles that match your search

Home rental in Radda in Chianti with swimming pool

Radda in Chianti house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £209 / night

£2,328 / week

1 / 63

Great rentals within 20 miles that match your search

Holiday studio in Siena

Siena studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £69 / night

£343 - £480 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Castelnuovo Berardenga

Castelnuovo Berardenga villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £2,029 / night

£14,198 / week

1 / 36

Great rentals within 20 miles that match your search

Apartment rental in Serre di Rapolano

Serre di Rapolano apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 15

Pricing unknown

1 / 7

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Castellina In Chianti

Castellina In Chianti house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £266 / night

£3,385 / week

1 / 38

Great rentals within 20 miles that match your search

Poggibonsi holiday apartment rental

Poggibonsi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £74 / night

£510 / week

1 / 11

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

from £98 / night

£108 - £657 / week

1 / 54

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