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920 Vacation rentals

Great rentals within 20 miles that match your search

Greve in Chianti Vacation apartment rental

Greve in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $92 / night

$641 / week

1 / 14

Great rentals within 20 miles that match your search

Home rental in Poggibonsi with swimming pool

Poggibonsi house

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 18

from $1,174 / night

$7,169 - $8,678 / week

1 / 36

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in Certaldo Alto

Certaldo Alto apartment

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

from $714 / night

$4,992 / week

1 / 11

Great rentals within 20 miles that match your search

Vacation home in San Donato in Poggio

San Donato in Poggio house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

from $296 / night

$1,699 - $2,328 / week

1 / 12

Great rentals within 20 miles that match your search

Home rental in Lucolena with swimming pool

Lucolena house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

from $330 / night

$2,013 - $4,528 / week

1 / 28

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 $977 / night

$6,105 / week

1 / 16

Great rentals within 20 miles that match your search

Vacation home with shared pool in San Gimignano

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $77 / night

$539 - $1,212 / week

1 / 10

Great rentals within 20 miles that match your search

Vacation home rental

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $114 / night

$794 - $1,513 / week

1 / 12

Great rentals within 20 miles that match your search

Vacation home with shared pool in San Donato in Poggio

San Donato in Poggio house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $224 / night

$1,334 - $1,799 / week

1 / 18

Great rentals within 20 miles that match your search

Certaldo Vacation apartment rental

Certaldo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $123 / night

$855 / week

1 / 4

Great rentals within 20 miles that match your search

Castelfiorentino Vacation home rental

Castelfiorentino house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $1,755 / night

$10,716 - $13,219 / week

1 / 28

Great rentals within 20 miles that match your search

Home rental in Castellina In Chianti with swimming pool

Castellina In Chianti house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

from $256 / night

$3,718 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in Il Pino

Il Pino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $873 / night

$6,105 / week

1 / 10

Great rentals within 20 miles that match your search

Vacation villa in Altopascio

Altopascio villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $140 / night

$785 / week

1 / 15

Great rentals within 20 miles that match your search

Vacation home with shared pool in Castellina In Chianti

Castellina In Chianti house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $436 / night

$2,660 - $3,055 / week

1 / 29

Great rentals within 20 miles that match your search

Castellina In Chianti Vacation apartment rental

Castellina In Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $115 / night

$1,325 / week

1 / 14

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in Il Pino

Il Pino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from $472 / night

$3,297 / week

1 / 6

Great rentals within 20 miles that match your search

Vacation home with shared pool in Montespertoli

Montespertoli house

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 8

Pricing unknown

1 / 12

Great rentals within 20 miles that match your search

Vacation home with shared pool in Castelfiorentino

Castelfiorentino house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $188 / night

$1,146 - $1,409 / week

1 / 25

Great rentals within 20 miles that match your search

Vacation farmhouse in San Gimignano

San Gimignano farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Pricing unknown

1 / 24

Great rentals within 20 miles that match your search

Castellina In Chianti Vacation home rental

Castellina In Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $342 / night

$2,087 - $2,466 / week

1 / 36

Great rentals within 20 miles that match your search

Home rental in Certaldo with swimming pool

Certaldo house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from $1,392 / night

$9,744 - $12,027 / week

1 / 18

Great rentals within 20 miles that match your search

Castelfiorentino Vacation home rental

Castelfiorentino house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $203 / night

$1,234 - $1,473 / week

1 / 23

Great rentals within 20 miles that match your search

Villa rental in Lucardo

Lucardo villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $61 / night

$403 / week

1 / 8

Great rentals within 20 miles that match your search

Vacation home with shared pool in Castelfiorentino

Castelfiorentino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $174 / night

$1,058 - $1,347 / week

1 / 22

Great rentals within 20 miles that match your search

Vacation home with shared pool in Castelfiorentino

Castelfiorentino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $174 / night

$1,058 - $1,347 / week

1 / 21

Great rentals within 20 miles that match your search

Castelfiorentino Vacation home rental

Castelfiorentino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $174 / night

$1,058 - $1,347 / week

1 / 25

Great rentals within 20 miles that match your search

Castelfiorentino Vacation home rental

Castelfiorentino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $174 / night

$1,058 - $1,347 / week

1 / 21

Great rentals within 20 miles that match your search

Castelfiorentino Vacation home rental

Castelfiorentino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $174 / night

$1,058 - $1,347 / week

1 / 22

Great rentals within 20 miles that match your search

Vacation home with shared pool in Castelfiorentino

Castelfiorentino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $174 / night

$1,058 - $1,347 / week

1 / 22

Great rentals within 20 miles that match your search

Vacation apartment in Il Pino

Il Pino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $929 / night

$6,504 / week

1 / 8

Great rentals within 20 miles that match your search

Vacation home with shared pool in Castelfiorentino

Castelfiorentino house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $203 / night

$1,234 - $1,473 / week

1 / 23

Great rentals within 20 miles that match your search

Home rental in San Donato in Poggio with shared pool

San Donato in Poggio house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $204 / night

$1,246 - $2,190 / week

1 / 25

Great rentals within 20 miles that match your search

Vacation home with shared pool in San Donato in Poggio

San Donato in Poggio house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $164 / night

$994 - $1,635 / week

1 / 14

Great rentals within 20 miles that match your search

Vacation home with shared pool in San Donato in Poggio

San Donato in Poggio house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $164 / night

$994 - $1,635 / week

1 / 17

Great rentals within 20 miles that match your search

Vacation home with shared pool in San Donato in Poggio

San Donato in Poggio house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $164 / night

$994 - $1,635 / week

1 / 14

Great rentals within 20 miles that match your search

Home rental in San Donato in Poggio with shared pool

San Donato in Poggio house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $164 / night

$994 - $1,635 / week

1 / 14

Great rentals within 20 miles that match your search

Castelfiorentino Vacation villa accommodation

Castelfiorentino villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $1,392 / night

$9,744 - $12,027 / week

1 / 43

Great rentals within 20 miles that match your search

Tavarnelle Val di Pesa Vacation villa rental

Tavarnelle Val di Pesa villa

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 20

from $1,894 / night

$13,255 - $19,286 / week

1 / 50

Great rentals within 20 miles that match your search

Vacation home rental

Barberino Val d'Elsa house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

from $691 / night

$4,838 / week

1 / 33