Updating

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

Holiday Rentals in Gaiole in Chianti - Holiday Lettings - Villas

All filters (3)

Filters (3)

Clear filters

7 Holiday homes

Applied filters (3)

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Bucine

Bucine villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from £590 / night

£4,813 - £5,893 / week

1 / 95

Great rentals within 20 miles that match your search

Villa rental in Rapale with swimming pool

Rapale villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 20

from £772 / night

£5,404 / week

1 / 50

Great rentals within 20 miles that match your search

Rapale holiday villa rental

Rapale villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 20

from £772 / night

£5,404 / week

1 / 50

Great rentals within 20 miles that match your search

Villa rental in Selvole with swimming pool

Selvole villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

from £2,342 / night

£16,391 - £28,271 / week

1 / 43

Great rentals within 20 miles that match your search

Siena holiday villa rental

Siena villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 10

from £685 / night

£4,792 / week

1 / 120

Great rentals within 20 miles that match your search

Holiday cottage in Montebenichi

Montebenichi cottage

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

from £722 / night

£5,053 - £7,540 / week

1 / 51

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Levane

Levane villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £606 / night

£4,243 - £6,483 / week

1 / 27

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

Clear all filters

Lucolena holiday villa rental

Lucolena villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

1 filter does not match: Fireplace

from £1,685 / night

£11,791 / week

1 / 22

Great rentals within 20 miles that match your search

Villa rental in Montefioralle

Montefioralle villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 16

1 filter does not match: Fireplace

from £1,475 / night

£10,320 / week

1 / 50

Great rentals within 20 miles that match your search

Holiday villa in Montefioralle

Montefioralle villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

1 filter does not match: Fireplace

from £1,373 / night

£9,612 / week

1 / 45

Great rentals within 20 miles that match your search

Montefioralle holiday villa rental

Montefioralle villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

1 filter does not match: Fireplace

from £1,302 / night

£9,110 / week

1 / 42

Great rentals within 20 miles that match your search

Loro Ciuffenna holiday farmhouse rental

Loro Ciuffenna farmhouse

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 filter does not match: TV

from £344 / night

£2,407 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday villa rental

Castellina In Chianti villa

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 18

1 filter does not match: TV

from £2,057 / night

£13,091 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday villa rental

Panzano in Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 20

1 filter does not match: Fireplace

from £1,970 / night

£13,786 - £27,572 / week

1 / 50

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Loro Ciuffenna

Loro Ciuffenna house

  • 11 bedrooms
  • 10 bathrooms
  • sleeps 23

1 filter does not match: TV

from £688 / night

£4,420 / week

1 / 46

Great rentals within 20 miles that match your search

Holiday home in Pergine Valdarno

Pergine Valdarno house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Fireplace

from £295 / night

£1,867 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Sogna

Sogna villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 14

1 filter does not match: Fireplace

from £610 / night

£4,270 / week

1 / 49

Great rentals within 20 miles that match your search

Villa rental in Bucine with swimming pool

Bucine villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Fireplace

from £632 / night

£5,404 / week

1 / 33

Great rentals within 20 miles that match your search

Sovicille holiday apartment rental

Sovicille apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Sauna

Pricing unknown

1 / 4

Great rentals within 20 miles that match your search

Holiday apartment with golf nearby in San Rocco a Pilli

San Rocco a Pilli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Sauna

from £138 / night

£963 / week

1 / 11

Great rentals within 20 miles that match your search

Holiday apartment in Monte San Savino

Monte San Savino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Sauna

from £63 / night

£440 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday apartment in Montevarchi

Montevarchi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Sauna

from £99 / night

£541 - £678 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday guest house in Panzano in Chianti

Panzano in Chianti guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

1 filter does not match: Sauna

from £59 / night

£413 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday villa rental

Bucine villa

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 24

1 filter does not match: Sauna

from £383 / night

£2,682 / week

1 / 31

Great rentals within 20 miles that match your search

Apartment rental in Monteriggioni

Monteriggioni apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Sauna

from £123 / night

£860 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday farmhouse in Terranuova Bracciolini

Terranuova Bracciolini farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Sauna

from £74 / night

£516 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday farmhouse in Terranuova Bracciolini

Terranuova Bracciolini farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Sauna

from £59 / night

£413 / week

1 / 19

Great rentals within 20 miles that match your search

B&b rental in Serre di Rapolano

Serre di Rapolano b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 filter does not match: Sauna

from £94 / night

£654 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday home with shared pool in Castelnuovo Berardenga

Castelnuovo Berardenga house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Sauna

from £227 / night

£1,589 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home with shared pool in Bucine

Bucine house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Sauna

from £64 / night

£447 - £791 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday villa in Siena

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Sauna

from £325 / night

£2,276 / week

1 / 19

Great rentals within 20 miles that match your search

Siena holiday villa rental

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Sauna

from £138 / night

£963 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday villa in Montevarchi

Montevarchi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Sauna

from £197 / night

£786 - £807 / week

1 / 11

Great rentals within 20 miles that match your search

Holiday b&b in Serre di Rapolano

Serre di Rapolano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Sauna

from £94 / night

£654 / week

1 / 21

Great rentals within 20 miles that match your search

Siena holiday townhouse accommodation

Siena townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Sauna

from £104 / night

£570 / week

1 / 56

Great rentals within 20 miles that match your search

Holiday b&b in Bucine

Bucine b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Sauna

from £295 / night

£1,965 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday townhouse in Terranuova Bracciolini

Terranuova Bracciolini townhouse

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 filter does not match: Sauna

from £49 / night

£374 / week

1 / 11

Great rentals within 20 miles that match your search

Siena holiday townhouse rental

Siena townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Sauna

from £118 / night

£825 / week

1 / 31

Great rentals within 20 miles that match your search

Campoli in Chianti holiday cottage rental

Campoli in Chianti cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Sauna

from £128 / night

£855 / week

1 / 57

Great rentals within 20 miles that match your search

Holiday villa rental

Montevarchi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Sauna

from £118 / night

£825 / week

1 / 4

×

Also consider