50 Best Tuscany villas on Holiday Lettings - Apartments

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  • Italy
  • Tuscany

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  • Province of Arezzo (1)
  • Province of Grosseto (3)

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40 Holiday homes

Travellers going to Tuscany are booking June dates now. Secure your holiday home today and have the perfect trip.

(1) Very Good 

1 / 31

Tuscany holiday bungalow rental

Province of Arezzo / Bucine

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay

from $23 / night

$159 - $198 / week

Book Book View

from $23 / night

(1) Excellent 

1 / 20

Holiday bungalow in Tuscany

Province of Grosseto / Montieri

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $75 / night

$447 - $475 / week

Book Book View

from $75 / night

1 / 12

Holiday bungalow in Tuscany

Province of Grosseto / Gavorrano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $85 / night

$566 - $747 / week

Book Book View

from $85 / night

Featured properties

1 / 7

Tuscany holiday bungalow rental

Province of Grosseto / Castiglione Della Pescaia

25 bedroomsSleeps 27 nights min stay

  • 25 bedrooms
  • Sleeps 2
  • 7 nights min stay

from $243 / night

$1697 / week

Book Book View

from $243 / night

More results near

Distance approx 1.13 miles from Tuscany Show on Map

1 / 25

Holiday townhouse in Tuscany

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $91 / night

$634 - $792 / week

Book Book View

from $91 / night

Distance approx 1.33 miles from Tuscany Show on Map

1 / 16

Holiday condo with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

9 bedroomsSleeps 16Min stay varies

  • 9 bedrooms
  • Sleeps 16
  • Min stay varies

from $566 / night

$3958 / week

Book Book View

from $566 / night

Distance approx 1.82 miles from Tuscany Show on Map

1 / 11

Villa rental in Tuscany with shared pool

Province of Siena / Castellina In Chianti

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay

from $198 / night

$1386 - $1584 / week

Book Book View

from $198 / night

Distance approx 1.82 miles from Tuscany Show on Map

(4) Very Good 

1 / 8

Holiday cottage with shared pool in Tuscany

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 57 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay

from $147 / night

$1018 - $1470 / week

Book Book View

from $147 / night

Distance approx 1.83 miles from Tuscany Show on Map

1 / 17

Cottage rental in Tuscany with shared pool

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $153 / night

$1069 - $1544 / week

Book Book View

from $153 / night

Distance approx 1.84 miles from Tuscany Show on Map

(1) Excellent 

1 / 19

Holiday villa rental

Province of Siena / Castellina In Chianti

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $207 / night

$1446 - $1886 / week

Book Book View

from $207 / night

Distance approx 1.86 miles from Tuscany Show on Map

1 / 24

Tuscany holiday apartment rental

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 8Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies

from $131 / night

$911 - $990 / week

Book Book View

from $131 / night

Distance approx 2.28 miles from Tuscany Show on Map

(2) Excellent 

1 / 32

Radda in Chianti holiday farmhouse rental

Province of Siena / Radda in Chianti

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $68 / night

$441 - $543 / week

Book Book View

from $68 / night

Distance approx 2.29 miles from Tuscany Show on Map

(3) Excellent 

1 / 29

Holiday farmhouse in Tuscany

Province of Siena / Radda in Chianti

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $108 / night

$622 - $735 / week

Book Book View

from $108 / night

Distance approx 2.29 miles from Tuscany Show on Map

(2) Excellent 

1 / 22

Farmhouse letting in Tuscany

Province of Siena / Radda in Chianti

2 bedroomsSleeps 3Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies

from $68 / night

$453 - $509 / week

Book Book View

from $68 / night

Distance approx 2.76 miles from Tuscany Show on Map

(1) Excellent 

1 / 24

Holiday villa rental

Province of Siena / Castellina In Chianti

3 bedroomsSleeps 77 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay

from $259 / night

$1813 / week

Book Book View

from $259 / night

Distance approx 2.77 miles from Tuscany Show on Map

(5) Excellent 

1 / 33

Farmhouse rental in Tuscany

Province of Siena / Radda in Chianti

2 bedroomsSleeps 3Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies

from $80 / night

$453 - $634 / week

Book Book View

from $80 / night

Distance approx 2.8 miles from Tuscany Show on Map

(1) Excellent 

1 / 16

Holiday apartment with shared pool in Tuscany

Castellina In Chianti / Cagnano di Sotto

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from $106 / night

$737 / week

Book Book View

from $106 / night

Distance approx 2.88 miles from Tuscany Show on Map

(1) Excellent 

1 / 11

Holiday b&b with shared pool in Panzano in Chianti

Greve in Chianti / Panzano in Chianti

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $97 / night

$656 - $735 / week

Book Book View

from $97 / night

Distance approx 3.05 miles from Tuscany Show on Map

(2) Excellent 

1 / 48

Holiday cottage in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay

from $136 / night

$622 - $735 / week

Book Book View

from $136 / night

Distance approx 3.12 miles from Tuscany Show on Map

(3) Very Good 

1 / 59

Cottage rental in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay

from $136 / night

$622 - $735 / week

Book Book View

from $136 / night

Distance approx 3.15 miles from Tuscany Show on Map

(1) Very Good 

1 / 10

Apartment rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $112 / night

$735 - $1131 / week

Book Book View

from $112 / night

Distance approx 3.25 miles from Tuscany Show on Map

1 / 8

Holiday apartment in Tuscany

Province of Siena / Radda in Chianti

1 bedroomSleeps 27 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay

from $57 / night

$396 / week

Book Book View

from $57 / night

Distance approx 3.37 miles from Tuscany Show on Map

1 / 24

Holiday farmhouse with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $227 / night

$1357 - $2375 / week

Book Book View

from $227 / night

Distance approx 3.41 miles from Tuscany Show on Map

1 / 23

Holiday farmhouse rental

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

Pricing unknown

Book Book View

Pricing unknown

Distance approx 3.41 miles from Tuscany Show on Map

1 / 14

Holiday farmhouse rental

Province of Siena / Castellina In Chianti

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

Pricing unknown

Book Book View

Pricing unknown

Distance approx 3.41 miles from Tuscany Show on Map

1 / 14

Holiday farmhouse letting

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 7Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies

Pricing unknown

Book Book View

Pricing unknown

Distance approx 3.42 miles from Tuscany Show on Map

1 / 18

Holiday farmhouse in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies

Pricing unknown

Book Book View

Pricing unknown

Distance approx 3.42 miles from Tuscany Show on Map

1 / 13

Holiday farmhouse in Tuscany

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $170 / night

$679 - $1697 / week

Book Book View

from $170 / night

Distance approx 3.68 miles from Tuscany Show on Map

(4) Excellent 

1 / 18

Holiday apartment with swimming pool in Tuscany

Barberino Val d'Elsa / San Silvestro

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $136 / night

$679 - $1188 / week

Book Book View

from $136 / night

Distance approx 3.7 miles from Tuscany Show on Map

(14) Very Good 

1 / 20

Holiday apartment with swimming pool in Barberino Val d'Elsa

Barberino Val d'Elsa / San Silvestro

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $147 / night

$735 - $1301 / week

Book Book View

from $147 / night

Distance approx 3.85 miles from Tuscany Show on Map

1 / 14

Castellina In Chianti holiday apartment rental

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 55 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min stay

from $242 / night

$1448 - $1869 / week

Book Book View

from $242 / night

Distance approx 3.86 miles from Tuscany Show on Map

1 / 22

Villa rental in Tuscany with swimming pool

Province of Siena / Castellina In Chianti

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay

from $752 / night

$5259 / week

Enquire Enquire View

from $752 / night

Distance approx 3.86 miles from Tuscany Show on Map

1 / 24

Holiday villa letting

Province of Siena / Castellina In Chianti

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay

from $752 / night

$5259 / week

Enquire Enquire View

from $752 / night

Distance approx 3.9 miles from Tuscany Show on Map

(2) Very Good 

1 / 41

Holiday barn with shared pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from $128 / night

$894 - $1572 / week

Book Book View

from $128 / night

Distance approx 3.9 miles from Tuscany Show on Map

(1) Very Good 

1 / 29

Holiday home with swimming pool in Tuscany

Province of Florence / San Donato in Poggio

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $170 / night

$1075 - $1979 / week

Enquire Enquire View

from $170 / night

Distance approx 3.91 miles from Tuscany Show on Map

1 / 72

Villa rental in Tuscany with indoor pool

Province of Siena / Castelnuovo Berardenga

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $227 / night

$1346 - $2703 / week

Book Book View

from $227 / night

Distance approx 4.06 miles from Tuscany Show on Map

1 / 13

Holiday cottage with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $170 / night

$1018 - $1256 / week

Book Book View

from $170 / night

Distance approx 4.35 miles from Tuscany Show on Map

1 / 14

Holiday apartment rental

Province of Siena / Gaiole in Chianti

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $105 / night

$0 / week

Book Book View

from $105 / night

Distance approx 4.37 miles from Tuscany Show on Map

(1) Excellent 

1 / 27

Holiday villa in Tuscany

Province of Florence / San Donato in Poggio

3 bedroomsSleeps 82 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $396 / night

$2488 / week

Book Book View

from $396 / night

Distance approx 4.59 miles from Tuscany Show on Map

1 / 18

Holiday apartment with swimming pool in Tuscany

Province of Siena / Poggibonsi

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $193 / night

$1346 / week

Book Book View

from $193 / night

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