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331 Vacation rentals

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Horse riding

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

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

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

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 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 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 condo in Marcialla

Marcialla condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Pricing unknown

1 / 11

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in San Casciano in Val di Pesa

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $159 / night

$949 - $1,240 / week

1 / 22

Great rentals within 20 miles that match your search

Apartment rental in Certaldo with shared pool

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $175 / night

$1,221 / week

1 / 5

Great rentals within 20 miles that match your search

Vacation villa with swimming pool in Poggibonsi

Poggibonsi villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from $641 / night

$6,889 / week

1 / 60

Great rentals within 20 miles that match your search

San Casciano in Val di Pesa Vacation apartment rental

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $159 / night

$949 - $1,240 / week

1 / 26

Great rentals within 20 miles that match your search

Apartment rental in San Casciano in Val di Pesa with shared pool

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $159 / night

$949 - $1,240 / week

1 / 28

Great rentals within 20 miles that match your search

Home rental in Castelnuovo Berardenga with swimming pool

Castelnuovo Berardenga house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from $512 / night

$6,060 / week

1 / 32

Great rentals within 20 miles that match your search

Apartment rental in San Casciano in Val di Pesa with shared pool

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $306 / night

$1,368 - $1,838 / week

1 / 29

Great rentals within 20 miles that match your search

Vacation villa rental

Greve in Chianti villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 16

from $3,663 / night

$25,641 / week

1 / 55

Great rentals within 20 miles that match your search

Barberino Val d'Elsa Vacation farmhouse rental

Barberino Val d'Elsa farmhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Pricing unknown

1 / 7

Great rentals within 20 miles that match your search

Vacation apartment in Certaldo

Certaldo apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $245 / night

$1,712 / week

1 / 5

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in San Casciano in Val di Pesa

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $263 / night

$1,180 - $1,539 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in San Casciano in Val di Pesa

San Casciano in Val di Pesa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from $367 / night

$1,667 - $2,308 / week

1 / 27

Great rentals within 20 miles that match your search

Apartment rental in San Casciano in Val di Pesa with shared pool

San Casciano in Val di Pesa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $367 / night

$1,667 - $2,308 / week

1 / 30

Great rentals within 20 miles that match your search

San Casciano in Val di Pesa Vacation villa rental

San Casciano in Val di Pesa villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from $965 / night

$5,043 - $7,180 / week

1 / 44

Great rentals within 20 miles that match your search

San Casciano in Val di Pesa Vacation apartment rental

San Casciano in Val di Pesa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $367 / night

$1,667 - $2,308 / week

1 / 33

Great rentals within 20 miles that match your search

Ulignano Vacation villa rental

Ulignano villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from $515 / night

$3,602 / week

1 / 20

Great rentals within 20 miles that match your search

Vacation apartment in Tavarnelle Val di Pesa

Tavarnelle Val di Pesa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $96 / night

$611 / week

1 / 19

Great rentals within 20 miles that match your search

Certaldo Vacation villa rental

Certaldo villa

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 15

from $2,320 / night

$16,240 / week

1 / 19

Great rentals within 20 miles that match your search

Vacation apartment in Certaldo Alto

Certaldo Alto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $143 / night

$999 / week

1 / 4

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in San Casciano in Val di Pesa

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $306 / night

$1,368 - $1,838 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation apartment with shared pool in San Casciano in Val di Pesa

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $306 / night

$1,368 - $1,838 / week

1 / 28

Great rentals within 20 miles that match your search

San Casciano in Val di Pesa Vacation apartment rental

San Casciano in Val di Pesa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $159 / night

$949 - $1,240 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation villa rental

Staggia Senese villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

from $603 / night

$4,218 / week

1 / 62

Great rentals within 20 miles that match your search

Vacation apartment in Certaldo

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $153 / night

$1,070 / week

1 / 5

Great rentals within 20 miles that match your search

Apartment rental in San Gimignano

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
14 reviews

from $123 / night

$733 / week

1 / 27

Great rentals within 20 miles that match your search

Vacation guest house with golf nearby in San Gimignano

San Gimignano guest house

  • 10 bedrooms
  • 5 bathrooms
  • sleeps 20

from $843 / night

$5,495 - $7,546 / week

1 / 29

Great rentals within 20 miles that match your search

Vacation apartment in Certaldo

Certaldo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $102 / night

$714 / week

1 / 3

Great rentals within 20 miles that match your search

Vacation villa with swimming pool in San Casciano in Val di Pesa

San Casciano in Val di Pesa villa

  • 11 bedrooms
  • 10 bathrooms
  • sleeps 15

from $1,360 / night

$9,518 / week

1 / 27

Great rentals within 20 miles that match your search

Vacation home with swimming pool in San Gimignano

San Gimignano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $295 / night

$3,541 / week

1 / 17

Great rentals within 20 miles that match your search

Monteriggioni Vacation villa rental

Monteriggioni villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
5 reviews

from $196 / night

$1,368 - $3,248 / week

1 / 108

Great rentals within 20 miles that match your search

Vacation villa in Certaldo

Certaldo villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 18

from $572 / night

$4,001 / week

1 / 110

Great rentals within 20 miles that match your search

Vacation villa accommodation

San Casciano in Val di Pesa villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 15

from $1,710 / night

$10,864 - $12,821 / week

1 / 28

Great rentals within 20 miles that match your search

Vacation home with swimming pool in Radda in Chianti

Radda in Chianti house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

from $511 / night

$8,795 / week

1 / 54