Villas in Province of Siena: Rent luxury villas in Province of Siena

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Province of Siena

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826 Holiday homes

Filters applied: Villa

(5) Excellent 

21

Holiday villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“An awesome villa in the Tuscan hills” A wonderfully restored church with plenty of character. Privacy with trees and hedges. Fab and accessible pool. Well equipped kitchen. An amazing welcome pack. We cycled from here to San Gimignano and to Monterigg
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from £132 / night

£878 - £2018 / week

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Responds fast!
avg. 49 minutes

from £132 / night

(67) Excellent 

52

Holiday villa letting

Province of Siena / Sinalunga

12 26 Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
  • Nearest beach 170 km
  • Swimming pool
  • Child friendly

from £527 / night

£3685 - £7895 / week

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from £527 / night

(12) Excellent 

69

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“A hidden gem.” We stayed at Villa LisiDor at the end of May with family. We made the trip to Tuscany by train to Florence from the UK and hired a car from there. We arrived during an unseasonably chilly spell and in torrential rain after a very l
…see more

from £416 / night

£2908 - £4474 / week

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from £416 / night

16

Holiday villa rental

Province of Siena / Cetona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Pet friendly
  • Private garden

from £270 / night

£1890 - £3780 / week

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from £270 / night

(6) Excellent 

36

Holiday villa with indoor pool in Radicondoli

Province of Siena / Radicondoli

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 79 km
  • Swimming pool
  • Child friendly

from £264 / night

£1843 / week

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Responds fast!
avg. 27 minutes

from £264 / night

(2) Excellent 

63

Villa rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly

from £527 / night

£3422 - £3772 / week

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from £527 / night

(13) Very Good 

28

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Villa PetrAlexa - excellent leisure facility” This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfec
…see more

from £126 / night

£878 - £2106 / week

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from £126 / night

36

Holiday villa in Siena

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly

from £483 / night

£2632 - £4386 / week

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from £483 / night

(6) Very Good 

39

Holiday villa rental

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £176 / night

£1316 - £2369 / week

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Responds fast!
avg. 3 hours 47 minutes

from £176 / night

24

Holiday villa in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

9 18 Min stay varies

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

from £286 / night

£1746 - £2939 / week

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from £286 / night

(1) Excellent 

99

Holiday villa with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £110 / night

£676 - £1009 / week

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from £110 / night

60

Holiday villa with swimming pool in Bettolle

Sinalunga / Bettolle

11 22 7 nights min

  • 11 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £799 / night

£5593 - £7128 / week

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from £799 / night

(2) Very Good 

27

San Gusme holiday villa rental

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Private garden
“wonderful and peaceful place” San Donato is very quiet, a very beautiful place, the garden and all the Villa Arceno aera are amazing, the house is simple but comfortable, and with a soul, as if you ever know this place, I will return one day, for sure
…see more

from £187 / night

£1308 - £1746 / week

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from £187 / night

(1) Excellent 

20

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

from £163 / night

£1141 - £1799 / week

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from £163 / night

(7) Excellent 

24

Val d'Orcia holiday villa rental

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £276 / night

£1930 - £2110 / week

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from £276 / night

(1) Excellent 

7

Murlo holiday villa rental

Province of Siena / Murlo

8 13 2 nights min

  • 8 bedrooms
  • Sleeps 13
  • 2 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £527 / night

£3158 / week

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from £527 / night

(1) Very Good 

35

Villa accommodation in San Gimignano with swimming pool

Province of Siena / San Gimignano

7 10 Min stay varies

  • 7 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £189 / night

£1316 - £2106 / week

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from £189 / night

(10) Excellent 

122

Cetona holiday villa rental

Province of Siena / Cetona

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £571 / night

£2579 - £3586 / week

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from £571 / night

(4) Excellent 

24

Holiday villa with swimming pool in Radicondoli

Radicondoli / Belforte

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
“Tuscany - just as we imagined!” A delightful villa with all mod cons but the feel of historic, authentic Tuscany. Situated in a tiny village, we appeared to be the only non residents and we didn't feel that we were in tourist territory. However, San
…see more

from £176 / night

£1229 - £1781 / week

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from £176 / night

(1) Excellent 

24

Villa rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £400 / night

£2400 - £4143 / week

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Responds fast!
avg. 3 hours 43 minutes

from £400 / night

100

Cetona holiday villa rental

Province of Siena / Cetona

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly

from £395 / night

£2632 - £4913 / week

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from £395 / night

(1) Excellent 

24

Holiday villa with swimming pool in Poggibonsi

Province of Siena / Poggibonsi

7 18 7 nights min

  • 7 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £242 / night

£1693 - £4079 / week

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Responds fast!
avg. 3 hours 14 minutes

from £242 / night

(4) Excellent 

17

Holiday villa rental

Province of Siena / Gaiole in Chianti

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
“Authentic unspoiled Italian charm!” My family and I stayed at this beautiful property and had a relaxed and wonderful holiday. Gaiole in Chianti is a small village totally unspoilt by tourism and the location of this property is ideal if you hire a ca
…see more

from £106 / night

£527 / week

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Responds fast!
avg. 2 hours 44 minutes

from £106 / night

(1) Excellent 

22

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £250 / night

£1750 - £2460 / week

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from £250 / night

33

Montalcino holiday villa rental

Province of Siena / Montalcino

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £176 / night

£1229 / week

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Responds fast!
avg. 2 hours 36 minutes

from £176 / night

(1) Excellent 

32

Holiday villa with swimming pool in Rigaiolo

Sinalunga / Rigaiolo

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

from £185 / night

£1290 - £2979 / week

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from £185 / night

(3) Excellent 

22

Villa rental in Siena with swimming pool

Province of Siena / Siena

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly

from £351 / night

£2018 - £3509 / week

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from £351 / night

25

Holiday villa with swimming pool in Sinalunga

Province of Siena / Sinalunga

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £251 / night

£1755 - £3422 / week

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from £251 / night

14

Holiday villa with swimming pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £276 / night

£1930 - £2808 / week

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from £276 / night

32

Farnetella holiday villa rental

Sinalunga / Farnetella

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £176 / night

£1229 - £2281 / week

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from £176 / night

(2) Excellent 

24

Holiday villa with swimming pool in Montalcinello

Chiusdino / Montalcinello

8 18 7 nights min

  • 8 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly

from £345 / night

£2413 - £3948 / week

Enquire View

from £345 / night

(1) Very Good 

19

Montisi holiday villa rental

Province of Siena / Montisi

5 6 Min stay varies

  • 5 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £131 / night

£873 - £1575 / week

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Responds fast!
avg. 2 hours 57 minutes

from £131 / night

(4) Excellent 

22

Holiday villa rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £259 / night

£1097 - £2325 / week

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Responds fast!
avg. 3 hours 55 minutes

from £259 / night

100

Gaiole in Chianti holiday villa rental

Province of Siena / Gaiole in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

from £404 / night

£2808 - £4123 / week

Enquire View

from £404 / night

100

Holiday villa with swimming pool in Castelmuzio

Province of Siena / Castelmuzio

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £439 / night

£3071 - £4167 / week

Enquire View

from £439 / night

24

Holiday villa rental

Province of Siena / Cetona

10 20 2 nights min

  • 10 bedrooms
  • Sleeps 20
  • 2 nights min
  • Ask owner if suitable for children

from £1009 / night

£2881 - £4010 / week

Enquire View

from £1009 / night

(1) Excellent 

30

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect.” The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arri
…see more

from £258 / night

£1800 - £2579 / week

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Responds fast!
avg. 3 hours 11 minutes

from £258 / night

(2) Very Good 

22

Villa rental in Montepulciano

Province of Siena / Montepulciano

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 180 km
  • Child friendly
  • Pet friendly

from £88 / night

£527 / week

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from £88 / night

20

Villa rental in Castiglione D'Orcia with swimming pool

Province of Siena / Castiglione D'Orcia

1 21 7 nights min

  • 1 bedroom
  • Sleeps 21
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £633 / night

£4430 - £6356 / week

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from £633 / night

19

Holiday villa with swimming pool in Siena

Province of Siena / Siena

18 35 7 nights min

  • 18 bedrooms
  • Sleeps 35
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £3748 / night

£26230 - £53850 / week

Enquire View

from £3748 / night

1