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Vacation homes - vacation rentals

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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 $1,191 / night

$7,277 - $8,809 / 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 $724 / night

$5,066 / 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 $300 / night

$1,724 - $2,363 / 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 $335 / night

$2,043 - $4,596 / 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 $993 / night

$6,207 / 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 $78 / night

$547 - $1,230 / 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 $115 / night

$806 - $1,536 / 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 $227 / night

$1,354 - $1,826 / 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 $125 / night

$869 / 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 $1,781 / night

$10,877 - $13,418 / 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 $259 / night

$3,774 / 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 $888 / night

$6,207 / week

1 / 10

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 $443 / night

$2,700 - $3,101 / 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 $117 / night

$1,345 / 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 $480 / night

$3,352 / week

1 / 6

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 $191 / night

$1,163 - $1,431 / 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 $347 / night

$2,118 - $2,503 / 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 $1,413 / night

$9,891 - $12,208 / 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 $206 / night

$1,252 - $1,495 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation finca with shared pool in Greti

Greti finca

  • 17 bedrooms
  • 10 bathrooms
  • sleeps 34

from $2,235 / night

$13,655 / week

1 / 21

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 $176 / night

$1,074 - $1,367 / 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 $176 / night

$1,074 - $1,367 / 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 $176 / night

$1,074 - $1,367 / 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 $176 / night

$1,074 - $1,367 / 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 $176 / night

$1,074 - $1,367 / 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 $176 / night

$1,074 - $1,367 / week

1 / 22

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 $206 / night

$1,252 - $1,495 / 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 $207 / night

$1,265 - $2,223 / 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 $166 / night

$1,009 - $1,660 / 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 $166 / night

$1,009 - $1,660 / 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 $166 / night

$1,009 - $1,660 / 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 $166 / night

$1,009 - $1,660 / 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 $1,413 / night

$9,891 - $12,208 / week

1 / 43

Great rentals within 20 miles that match your search

Vacation home rental

Barberino Val d'Elsa house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

from $703 / night

$4,919 / week

1 / 33

Great rentals within 20 miles that match your search

Home rental in Castellina In Chianti with swimming pool

Castellina In Chianti house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $217 / night

$3,306 / week

1 / 25

Great rentals within 20 miles that match your search

Vacation home rental

Castellina In Chianti house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

from $175 / night

$2,143 / week

1 / 22

Great rentals within 20 miles that match your search

San Donato in Poggio Vacation home rental

San Donato in Poggio house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $134 / night

$818 - $1,367 / week

1 / 21

Great rentals within 20 miles that match your search

San Donato in Poggio Vacation home rental

San Donato in Poggio house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $134 / night

$818 - $1,367 / 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

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $134 / night

$818 - $1,367 / week

1 / 17