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Province of Siena Holidays & City Breaks - Holiday Lettings

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340 properties suitable for city breaks and holidays

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Holiday farmhouse in San Giovanni d'Asso

San Giovanni d'Asso farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £177 / night

£1,277 / week

1 / 17

Holiday b&b in Acquaviva di Montepulciano

Acquaviva di Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £69 / night

£550 - £688 / week

1 / 20

Ski home to rent in Abbadia San Salvatore

Abbadia San Salvatore house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

from £128 / night

£894 / week

1 / 14

Holiday condo in Montepulciano

Montepulciano condo

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

from £177 / night

£1,474 / week

1 / 35

Apartment rental in San Felice with shared pool

San Felice apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £128 / night

£884 / week

1 / 12

Chianciano Terme holiday penthouse rental

Chianciano Terme penthouse

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Pricing unknown

1 / 6

Farmhouse letting in Radda in Chianti

Radda in Chianti farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £84 / night

£541 - £776 / week

1 / 47

Townhouse letting in Rocca d'Orcia

Rocca d'Orcia townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £89 / night

£491 / week

1 / 21

Holiday villa with swimming pool in Siena

Siena villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

from £747 / night

£4,420 - £9,743 / week

1 / 233

Holiday apartment in Staggia Senese

Staggia Senese apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

from £69 / night

£462 / week

1 / 13

Holiday apartment in Castelnuovo Berardenga

Castelnuovo Berardenga apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £268 / night

£1,866 / week

1 / 20

Holiday apartment in Rocca d'Orcia

Rocca d'Orcia apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £118 / night

£491 / week

1 / 5

Holiday apartment in Radicondoli

Radicondoli apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £84 / night

£413 / week

1 / 17

Holiday apartment in Cetona

Cetona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Pricing unknown

1 / 12

Apartment rental in San Gimignano

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £84 / night

£580 - £590 / week

1 / 27

Holiday guest house with golf nearby in San Gimignano

San Gimignano guest house

  • 10 bedrooms
  • 5 bathrooms
  • sleeps 20

from £678 / night

£4,420 - £6,070 / week

1 / 29

Holiday farmhouse with shared pool, golf nearby in Monteriggioni

Monteriggioni farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Pricing unknown

1 / 4

Farmhouse accommodation in Cetona

Cetona farmhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £290 / night

£2,014 / week

1 / 10

Holiday villa with swimming pool in Murlo

Murlo villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Pricing unknown

1 / 24

Holiday b&b with swimming pool in Montepulciano

Montepulciano b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

from £983 / night

£6,875 / week

1 / 44

Apartment rental in Serre di Rapolano

Serre di Rapolano apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 15

Pricing unknown

1 / 7

Radicofani ski apartment to rent.

Radicofani apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £69 / night

£442 - £933 / week

1 / 26

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £94 / night

£580 / week

1 / 17

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

Pricing unknown

1 / 46

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £99 / night

£108 - £658 / week

1 / 54

San Gimignano holiday apartment rental

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £79 / night

£501 - £625 / week

1 / 53

Holiday farmhouse rental

Pienza farmhouse

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 14

Pricing unknown

1 / 7

Holiday villa in Siena

Siena villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £562 / night

£3,929 / week

1 / 10

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

Holiday farmhouse in Siena

Siena farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Pricing unknown

1 / 20

Farmhouse rental in Montisi

Montisi farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Pricing unknown

1 / 17

Sovicille holiday apartment rental

Sovicille apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Pricing unknown

1 / 4

Siena holiday b&b rental

Siena b&b

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £54 / night

£379 / week

1 / 15

Holiday apartment in Siena

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Pricing unknown

1 / 49

Holiday apartment in Siena

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Pricing unknown

1 / 47

Holiday apartment rental

San Felice apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £128 / night

£884 / week

1 / 12

Home rental in San Gimignano

San Gimignano house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £68 / night

£383 / week

1 / 47

Holiday apartment in Staggia Senese

Staggia Senese apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Pricing unknown

1 / 23

Trequanda holiday farmhouse rental

Trequanda farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Pricing unknown

1 / 13

Holiday apartment in Cetona

Cetona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £50 / night

£295 / week

1 / 19

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