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Vacation homes - vacation rentals

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32 Vacation rentals

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Vacation villa rental

Buonconvento villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

from $1,705 / night

$11,932 - $16,270 / week

1 / 41

Villa rental in Cetona

Cetona villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

from $2,789 / night

$19,525 - $31,456 / week

1 / 52

Buonconvento Vacation villa rental

Buonconvento villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 16

from $1,774 / night

$18,621 / week

1 / 49

Ski chalet to rent in Abbadia San Salvatore

Abbadia San Salvatore chalet

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $559 / night

$3,476 / week

1 / 72

Villa rental in Monticiano with swimming pool

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

from $3,625 / night

$25,370 - $33,815 / week

1 / 75

Buonconvento Vacation farmhouse rental

Buonconvento farmhouse

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 22

from $5,853 / night

$40,965 / week

1 / 39

Vacation villa rental

Trequanda villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

from $512 / night

$3,580 / week

1 / 48

Vacation apartment in San Gimignano

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $86 / night

$584 - $931 / week

1 / 20

Vacation villa rental

Castellina In Chianti villa

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 18

from $2,600 / night

$16,545 / week

1 / 10

Monteriggioni Vacation hotel apartment rental

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

Pricing unknown

1 / 12

Vacation home with swimming pool in Chianciano Terme

Chianciano Terme house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $355 / night

$3,966 / week

1 / 30

Villa rental in Casole d'Elsa with swimming pool

Casole d'Elsa villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from $987 / night

$6,906 / week

1 / 66

Vacation villa in San Benedetto

San Benedetto villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $694 / night

$4,858 / week

1 / 46

Acquaviva di Montepulciano Vacation apartment rental

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $236 / night

$1,267 - $1,813 / week

1 / 32

Apartment rental in Acquaviva di Montepulciano with shared pool

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $218 / night

$1,018 - $1,565 / week

1 / 30

Vacation villa rental

Chianciano Terme villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $361 / night

$2,169 - $3,470 / week

1 / 60

Acquaviva di Montepulciano Vacation apartment rental

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $156 / night

$745 - $1,080 / week

1 / 29

Acquaviva di Montepulciano Vacation apartment rental

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $156 / night

$745 - $1,068 / week

1 / 31

Chiusdino Vacation villa rental

Chiusdino villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $516 / night

$3,607 / week

1 / 59

Vacation villa with swimming pool in Montepulciano

Montepulciano villa

  • 5 bedrooms
  • 9 bathrooms
  • sleeps 9

from $1,242 / night

$8,690 / week

1 / 29

Acquaviva di Montepulciano Vacation apartment rental

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $218 / night

$1,018 - $1,569 / week

1 / 37

Villa rental in Selvole with swimming pool

Selvole villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

from $2,960 / night

$20,716 - $31,144 / week

1 / 43

Vacation apartment in Sarteano

Sarteano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $75 / night

$360 / week

1 / 18

Vacation townhouse in Gaiole in Chianti

Gaiole in Chianti townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from $249 / night

$1,738 / week

1 / 4

Vacation villa with swimming pool in Radicondoli

Radicondoli villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $301 / night

$1,912 - $2,781 / week

1 / 42

Vacation farmhouse in Ville di Corsano

Ville di Corsano farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $100 / night

$621 - $882 / week

1 / 33

Vacation villa with swimming pool in Sarteano

Sarteano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

from $862 / night

$6,030 / week

1 / 48

Vacation apartment in Chiusi

Chiusi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $123 / night

$861 / week

1 / 12

Apartment rental in Cetona

Cetona apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $249 / night

$1,614 - $3,352 / week

1 / 13

Siena Vacation villa rental

Siena villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 10

from $866 / night

$6,057 / week

1 / 120

Vacation b&b in Casole d'Elsa

Casole d'Elsa b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $65 / night

$452 / week

1 / 12

Vacation apartment with swimming pool in Montalcino

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $720 / night

$5,040 / week

1 / 25

Great rentals within 20 miles that match your search

Vacation home in Pergine Valdarno

Pergine Valdarno house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $373 / night

$2,359 / week

1 / 24

Vacation cottage in Montebenichi

Montebenichi cottage

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

from $913 / night

$6,386 - $9,530 / week

1 / 51

Villa rental in Rapale with swimming pool

Rapale villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 20

from $976 / night

$6,831 / week

1 / 50

Rapale Vacation villa rental

Rapale villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 20

from $976 / night

$6,831 / week

1 / 50

Lucolena Vacation villa rental

Lucolena villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

from $2,129 / night

$14,903 / week

1 / 22

Vacation villa with swimming pool in Sogna

Sogna villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 14

from $838 / night

$5,866 / week

1 / 49

Pozzo della Chiana Vacation villa rental

Pozzo della Chiana villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

from $1,517 / night

$10,619 / week

1 / 57

Montefioralle Vacation villa rental

Montefioralle villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from $1,645 / night

$11,514 / week

1 / 42

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