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Pienza Holidays & City Breaks - Holiday Lettings

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251 properties suitable for city breaks and holidays

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Holiday b&b in Monticchiello

Monticchiello b&b

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £88 / night

£581 - £2,614 / week

1 / 26

Holiday farmhouse rental

Pienza farmhouse

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 14

Pricing unknown

1 / 7

Pienza holiday apartment rental

Pienza apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £70 / night

£484 / week

1 / 12

Holiday b&b in Monticchiello

Monticchiello b&b

  • 1 bedroom
  • 3 bathrooms
  • sleeps 6

from £97 / night

£484 / week

1 / 10

B&b rental in Pienza

Pienza b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £73 / night

£509 / week

1 / 7

Pienza holiday apartment rental

Pienza apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £78 / night

£542 / week

1 / 16

Monticchiello holiday townhouse rental

Monticchiello townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £184 / night

£1,210 - £1,743 / week

1 / 41

Holiday apartment in Pienza

Pienza apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £194 / night

£1,355 / week

1 / 23

Holiday apartment rental

Monticchiello apartment

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 12

from £659 / night

£3,678 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday farmhouse with swimming pool in Lucignano

Lucignano farmhouse

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 28

Pricing unknown

1 / 48

Holiday apartment with shared pool in Cetona

Cetona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £138 / night

£802 / week

1 / 20

Holiday apartment in Sarteano

Sarteano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £58 / night

£281 / week

1 / 18

Holiday apartment with shared pool in Monteroni d'Arbia

Monteroni d'Arbia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £88 / night

£549 - £732 / week

1 / 19

Holiday apartment with shared pool in Monteroni d'Arbia

Monteroni d'Arbia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £88 / night

£549 - £732 / week

1 / 22

Montepulciano holiday apartment let

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £68 / night

£465 - £1,143 / week

1 / 11

Holiday villa with swimming pool in Pozzuolo

Pozzuolo villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

from £339 / night

£2,536 / week

1 / 53

Villa rental in Cortona with swimming pool

Cortona villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £107 / night

£678 - £968 / week

1 / 25

Holiday villa with swimming pool in Casale di Pari

Casale di Pari villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 20

from £1,743 / night

£12,196 / week

1 / 317

Holiday cottage in Cortona

Cortona cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Pricing unknown

1 / 30

Holiday villa with swimming pool in San Giovanni d'Asso

San Giovanni d'Asso villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

from £194 / night

£1,307 - £2,033 / week

1 / 39

Cortona holiday lodge rental

Cortona lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £77 / night

£562 - £659 / week

1 / 30

Holiday villa rental

San Giovanni d'Asso villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 14

from £484 / night

£3,388 - £5,034 / week

1 / 50

Lodge letting in Cortona with shared pool

Cortona lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £77 / night

£562 - £659 / week

1 / 30

Holiday guest house with shared pool in Chiusi

Chiusi guest house

  • 15 bedrooms
  • 12 bathrooms
  • sleeps 30

Pricing unknown

1 / 21

Holiday apartment with shared pool in Cortona

Cortona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £194 / night

£1,355 / week

1 / 19

Holiday apartment with shared pool in Sinalunga

Sinalunga apartment

  • 1 bedroom
  • 10 bathrooms
  • sleeps 2

Pricing unknown

1 / 30

Apartment rental in Castiglione del Lago

Castiglione del Lago apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £68 / night

£320 - £828 / week

1 / 21

San Casciano dei Bagni holiday home rental

San Casciano dei Bagni house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £58 / night

£436 - £1,046 / week

1 / 21

Holiday home with shared pool in Cortona

Cortona house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 6

Pricing unknown

1 / 12

Holiday apartment in Montepulciano

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £117 / night

£678 / week

1 / 26

Holiday apartment in Pozzuolo

Pozzuolo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £49 / night

£291 / week

1 / 20

Ski apartment to rent in Bagno Vignoni

Bagno Vignoni apartment

  • 1 bedroom
  • 3 bathrooms
  • sleeps 4

Pricing unknown

1 / 4

Chianciano Terme holiday penthouse rental

Chianciano Terme penthouse

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Pricing unknown

1 / 6

Holiday apartment in Montepulciano

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £88 / night

£513 / week

1 / 22

Holiday b&b with shared pool in Paciano

Paciano b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £58 / night

£388 / week

1 / 4

Holiday b&b with swimming pool in Palazzone

Palazzone b&b

  • 4 bedrooms
  • 7 bathrooms
  • sleeps 10

from £436 / night

£2,711 / week

1 / 35

Holiday finca rental

Radicofani finca

  • 2 bedrooms
  • 5 bathrooms
  • sleeps 4

Pricing unknown

1 / 10

Villa rental in Seggiano with shared pool

Seggiano villa

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 7

from £291 / night

£1,743 / week

1 / 20

Holiday farmhouse rental

Seggiano farmhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

from £218 / night

£1,307 / week

1 / 20

Holiday villa rental

Seggiano villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £121 / night

£726 / week

1 / 24

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