Holiday rentals in Province of Siena: Villas, Cottages and Apartments

Close

View larger map

Also consider

Europe Holidays
428241 properties
Italy Holidays
99720 properties
Tuscany Holidays
22686 properties
Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Villas San Gimignano
405 properties
Villas Siena
402 properties
Villas Montepulciano
283 properties
Casole d'Elsa
195 properties
Colle di Val d'Elsa
183 properties
Gaiole in Chianti
153 properties
Castelnuovo Berardenga
148 properties
Villas Castellina In Chianti
142 properties
Villas Pienza
138 properties
Rapolano Terme
135 properties
Poggibonsi
135 properties
Sinalunga
111 properties
Villas Montalcino
106 properties
Asciano
91 properties

Province of Siena

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

3,806 Holiday homes

(4) Excellent 

48

Province of Siena / Castiglione D'Orcia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Pet friendly

from £75 / night

£525 / week

Book View

from £75 / night

23

Holiday villa in Volpaia

Radda in Chianti / Volpaia

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden

from £303 / night

£2118 - £3345 / week

Enquire View

from £303 / night

6

Holiday apartment in Siena

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

from £85 / night

£572 - £631 / week

Book View

from £85 / night

(6) Excellent 

24

Holiday farmhouse with shared pool in Casole d'Elsa

Casole d'Elsa / Monteguidi

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 68 km
  • Swimming pool
  • Child friendly

from £93 / night

£632 - £904 / week

Book View

from £93 / night

5

Holiday apartment in Chiusi

Province of Siena / Chiusi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £135 / night

£715 / week

Book View

from £135 / night

(6) Very Good 

23

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

from £71 / night

£459 - £584 / week

Book View

from £71 / night

21

Poggibonsi holiday hotel apartment rental

Province of Siena / Poggibonsi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £110 / night

£765 - £1236 / week

Enquire View

from £110 / night

(1) Excellent 

22

Holiday apartment with shared pool in Castel San Gimignano

San Gimignano / Castel San Gimignano

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

from £65 / night

£408 - £731 / week

Book View

from £65 / night

18

Province of Siena / Asciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly

from £34 / night

£211 - £293 / week

Book View

from £34 / night

(1) Excellent 

22

Province of Siena / Gaiole in Chianti

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £241 / night

£1681 - £2690 / week

Book View

from £241 / night

13

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min

from £59 / night

£412 / week

Book View

from £59 / night

(4) Excellent 

19

Siena holiday apartment rental

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

from £68 / night

£421 - £656 / week

Book View

from £68 / night

100

Buonconvento holiday apartment rental

Province of Siena / Buonconvento

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £167 / night

£1110 - £1295 / week

Enquire View

from £167 / night

(1) Very Good 

20

Province of Siena / Rapolano Terme

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

from £58 / night

£337 - £884 / week

Book View

from £58 / night

26

Holiday guest house in Radicondoli

Province of Siena / Radicondoli

1 10 4 nights min

  • 1 bedroom
  • Sleeps 10
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly

from £337 / night

£2269 / week

Book View

from £337 / night

18

Apartment rental in Casole d'Elsa with shared pool

Casole d'Elsa / Monteguidi

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

from £89 / night

£622 - £1034 / week

Enquire View

from £89 / night

24

Holiday apartment in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly

from £59 / night

£412 - £772 / week

Enquire View

from £59 / night

8

Castelnuovo Berardenga / San Gusme

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

from £50 / night

£348 / week

Book View

from £50 / night

44

Radicondoli / Belforte

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £150 / night

£1055 - £1246 / week

Book View

from £150 / night

23

Apartment rental in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly

from £59 / night

£412 - £772 / week

Enquire View

from £59 / night

(4) Very Good 

17

Province of Siena / Torrita di Siena

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £43 / night

£295 / week

Book View

from £43 / night

(6) Excellent 

23

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
“Absolutely wonderful and picturesque!” We rented this beautiful house with two other couples for two weeks and absolutely loved our stay. Barbara and her family are gracious and kind hosts, always going our of their way to make our stay comfortable a
…see more

from £295 / night

£1303 - £2101 / week

Enquire View

from £295 / night

(12) Excellent 

50

Holiday villa with indoor pool, golf nearby in Gaiole in Chianti

Gaiole in Chianti / Montefienali

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £681 / night

£4765 - £7030 / week

Book View

from £681 / night

28

Holiday villa with swimming pool in Asciano

Province of Siena / Asciano

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £127 / night

£893 - £1498 / week

Book View

from £127 / night

5

San Rocco a Pilli holiday apartment rental

Sovicille / San Rocco a Pilli

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

from £101 / night

£673 / week

Book View

from £101 / night

(1) Average 

25

Province of Siena / San Quirico d'Orcia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £101 / night

£706 / week

Book View

from £101 / night

14

Holiday farmhouse rental

Casole d'Elsa / Monteguidi

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £80 / night

£554 - £831 / week

Book View

from £80 / night

15

Montalcino / Val d'Orcia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 80 km

from £85 / night

£589 / week

Book View

from £85 / night

(5) Very Good 

15

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

from £50 / night

£337 - £548 / week

Book View

from £50 / night

(1) Very Good 

5

Province of Siena / San Gimignano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Private garden

from £132 / night

£925 / week

Book View

from £132 / night

21

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly

from £47 / night

£328 - £619 / week

Enquire View

from £47 / night

(1) Very Good 

11

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

from £68 / night

£404 - £807 / week

Book View

from £68 / night

35

Holiday villa rental

Province of Siena / Ville di Corsano

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly

from £571 / night

£3992 - £6093 / week

Enquire View

from £571 / night

30

Montepulciano holiday watermill rental

Province of Siena / Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 16 km
  • Swimming pool
  • Child friendly

from £177 / night

£2009 - £2832 / week

Book View

from £177 / night

31

Province of Siena / Chianciano Terme

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Car not necessary
  • Pet friendly

from £67 / night

£412 - £648 / week

Book View

from £67 / night

20

Province of Siena / Castellina In Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £106 / night

£736 / week

Book View

from £106 / night

11

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £185 / night

£1136 - £1348 / week

Book View

from £185 / night

18

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £80 / night

£513 - £614 / week

Book View

from £80 / night

27

Montepulciano holiday villa rental

Province of Siena / Montepulciano

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool

from £570 / night

£3990 - £6589 / week

Book View

from £570 / night

17

Holiday farmhouse in Val d'Orcia

Montalcino / Val d'Orcia

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £361 / night

£2101 - £3362 / week

Enquire View

from £361 / night

1