Short city breaks Province of Siena

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  • Italy
  • Tuscany
  • Province of Siena

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  • Abbadia San Salvatore (1)
  • Asciano (23)
  • Bagni di San Filippo (1)
  • Bagno Vignoni (3)
  • Buonconvento (4)
  • Casciano (1)
  • Casole d'Elsa (32)
  • Castellina In Chianti (17)
  • Castelmuzio (2)
  • Castelnuovo Berardenga (13)
  • Castiglione D'Orcia (5)
  • Cetona (10)
  • Chianciano Terme (6)
  • Chiusdino (7)
  • Chiusi (4)
  • Colle di Val d'Elsa (17)
  • Gaiole in Chianti (13)
  • Montalcino (8)
  • Montepulciano (50)
  • Monteriggioni (19)
  • Monteroni d'Arbia (5)
  • Monticiano (6)
  • Montisi (6)
  • Murlo (6)
  • Palazzone (6)
  • Piancastagnaio (6)
  • Pienza (23)
  • Pievasciata (1)
  • Pievescola (6)
  • Poggibonsi (21)
  • Radda in Chianti (5)
  • Radicofani (18)
  • Radicondoli (24)
  • Rapolano Terme (17)
  • Rocca d'Orcia (2)
  • San Casciano dei Bagni (9)
  • San Gimignano (50)
  • San Giovanni d'Asso (5)
  • San Quirico d'Orcia (1)
  • Sarteano (7)
  • Siena (127)
  • Sinalunga (17)
  • Sovicille (26)
  • Torrita di Siena (4)
  • Trequanda (3)
  • Vivo d'Orcia (1)

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638 Holiday homes

Filters applied: City breaks (638)

Travellers going to Province of Siena are booking July dates now. Secure your holiday home today and have the perfect trip.

(1) Excellent 

1 / 14

Holiday home in Siena

Province of Siena / Siena

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $106 / night

$719 - $1107 / week

Book Book View

from $106 / night

(4) Excellent 

1 / 53

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa / Montegabbro

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $67 / night

$388 - $531 / week

Book Book View

from $67 / night

(5) Very Good 

1 / 15

Holiday apartment in Siena

Province of Siena / Siena

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $66 / night

$443 - $1582 / week

Book Book View

from $66 / night

Featured properties

(1) Excellent 

1 / 11

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $111 / night

$775 - $996 / week

Book Book View

from $111 / night

1 / 25

Holiday apartment in Siena

Province of Siena / Siena

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies

from $222 / night

$1549 / week

Book Book View

from $222 / night

1 / 31

Home rental in San Gimignano with shared pool

Province of Siena / San Gimignano

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $119 / night

$830 - $1084 / week

Book Book View

from $119 / night

(14) Excellent 

1 / 23

Castelnuovo Berardenga holiday apartment rental

Province of Siena / Castelnuovo Berardenga

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $100 / night

$554 - $1107 / week

Book Book View

from $100 / night

(5) Excellent 

1 / 33

Farmhouse rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 bedroomsSleeps 3Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies

from $78 / night

$443 - $620 / week

Book Book View

from $78 / night

(5) Excellent 

1 / 41

Holiday townhouse rental

Sinalunga / Rigomagno

5 bedroomsSleeps 102 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min stay

from $89 / night

$554 / week

Book Book View

from $89 / night

(2) Excellent 

1 / 40

Holiday b&b rental

Monticiano / Iesa Palazzo

6 bedroomsSleeps 121 night min stay

  • 6 bedrooms
  • Sleeps 12
  • 1 night min stay

from $89 / night

$620 / week

Book Book View

from $89 / night

(1) Excellent 

1 / 13

Holiday cottage with shared pool in Crete Senesi

Asciano / Crete Senesi

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $111 / night

$874 - $941 / week

Book Book View

from $111 / night

(4) Excellent 

1 / 24

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 bedroomSleeps 47 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay

from $88 / night

$614 - $701 / week

Book Book View

from $88 / night

1 / 28

Holiday townhouse in San Gimignano

Province of Siena / San Gimignano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $133 / night

$775 - $996 / week

Book Book View

from $133 / night

(5) Very Good 

1 / 23

Holiday apartment rental

Province of Siena / Montepulciano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $95 / night

$609 - $730 / week

Book Book View

from $95 / night

(1) Excellent 

1 / 24

Villa rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

7 bedroomsSleeps 145 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 5 nights min stay

from $862 / night

$4309 - $5193 / week

Book Book View

from $862 / night

(3) Very Good 

1 / 15

Siena holiday home rental

Province of Siena / Siena

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay

from $83 / night

$554 / week

Book Book View

from $83 / night

(6) Very Good 

1 / 45

Montepulciano holiday home rental

Province of Siena / Montepulciano

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies

from $83 / night

$554 - $664 / week

Book Book View

from $83 / night

1 / 24

Sinalunga holiday b&b rental

Province of Siena / Sinalunga

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies

from $106 / night

$653 - $930 / week

Book Book View

from $106 / night

(2) Excellent 

1 / 35

Holiday apartment letting

Province of Siena / Montepulciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $78 / night

$443 - $664 / week

Book Book View

from $78 / night

1 / 23

Cottage rental in Casole d'Elsa with shared pool

Province of Siena / Casole d'Elsa

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $72 / night

$432 - $686 / week

Book Book View

from $72 / night

(3) Very Good 

1 / 11

Holiday farmhouse rental

Castelnuovo Berardenga / San Gusme

2 bedroomsSleeps 54 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min stay

from $155 / night

$885 - $1051 / week

Book Book View

from $155 / night

(14) Very Good 

1 / 27

Holiday apartment in Sant Andrea a Montecchio

Siena / Sant Andrea a Montecchio

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $78 / night

$554 - $664 / week

Book Book View

from $78 / night

1 / 14

Holiday home in Casole d'Elsa

Province of Siena / Casole d'Elsa

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $100 / night

$576 - $1162 / week

Book Book View

from $100 / night

1 / 24

Holiday cottage in Siena

Province of Siena / Siena

3 bedroomsSleeps 82 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $166 / night

$1107 - $2047 / week

Book Book View

from $166 / night

(4) Excellent 

1 / 17

Holiday apartment in Monteriggioni

Province of Siena / Monteriggioni

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $78 / night

$498 - $664 / week

Book Book View

from $78 / night

(1) Very Good 

1 / 30

Holiday apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $165 / night

$1095 - $1660 / week

Book Book View

from $165 / night

(26) Excellent 

1 / 20

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay

from $89 / night

$598 - $742 / week

Book Book View

from $89 / night

1 / 27

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay

from $1217 / night

$8517 - $11282 / week

Book Book View

from $1217 / night

1 / 22

Holiday villa in Sovicille

Province of Siena / Sovicille

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $166 / night

$1107 / week

Book Book View

from $166 / night

(2) Very Good 

1 / 24

Holiday apartment in Siena

Province of Siena / Siena

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $81 / night

$465 - $744 / week

Book Book View

from $81 / night

1 / 17

Siena holiday apartment rental

Province of Siena / Siena

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from $222 / night

$0 / week

Book Book View

from $222 / night

(2) Good 

1 / 31

Holiday apartment in Siena

Province of Siena / Siena

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay

from $95 / night

$659 - $968 / week

Book Book View

from $95 / night

(1) Excellent 

1 / 35

Holiday apartment in Radicondoli

Province of Siena / Radicondoli

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay

from $111 / night

$775 / week

Book Book View

from $111 / night

1 / 30

Apartment accommodation in Poggibonsi with swimming pool

Province of Siena / Poggibonsi

3 bedroomsSleeps 4Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies

from $144 / night

$1007 - $1770 / week

Book Book View

from $144 / night

1 / 13

Piancastagnaio ski home to rent.

Piancastagnaio / Casa del Corto

3 bedroomsSleeps 82 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $155 / night

$1084 / week

Book Book View

from $155 / night

(4) Excellent 

1 / 16

B&b rental in Serre di Rapolano

Rapolano Terme / Serre di Rapolano

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay

from $106 / night

$736 / week

Book Book View

from $106 / night

(1) Excellent 

1 / 10

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from $67 / night

$0 / week

Book Book View

from $67 / night

(2) Excellent 

1 / 25

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $155 / night

$996 / week

Book Book View

from $155 / night

(1) Excellent 

1 / 30

Holiday apartment in Siena

Province of Siena / Siena

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay

from $81 / night

$465 - $744 / week

Book Book View

from $81 / night

1 / 21

Holiday guest house in San Gimignano

Province of Siena / San Gimignano

10 bedroomsSleeps 221 night min stay

  • 10 bedrooms
  • Sleeps 22
  • 1 night min stay

from $764 / night

$5188 / week

Book Book View

from $764 / night

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