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

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Province of Siena

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765 Holiday homes

Filters applied: Villa

(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 £255 / night

£1780 / week

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Responds fast!
avg. 28 minutes

from £255 / night

(7) 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 £170 / night

£907 - £2289 / week

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from £170 / night

(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 £128 / night

£848 - £1950 / week

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Responds fast!
avg. 49 minutes

from £128 / 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 £322 / night

£2248 - £4323 / week

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from £322 / night

34

Holiday villa in Pienza

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £199 / night

£1390 - £2272 / week

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from £199 / night

99

Montepulciano / Abbadia di Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Private garden

from £424 / night

£2967 / week

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from £424 / night

31

Asciano holiday villa let

Province of Siena / Asciano

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £295 / night

£1639 - £3530 / week

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from £295 / night

(10) Excellent 

58

Holiday villa rental

Province of Siena / San Giovanni d'Asso

8 16 3 nights min

  • 8 bedrooms
  • Sleeps 16
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“unforgettable tuscan paradise” Wonderful historic house, charming atmosphere, you feel at home. We were a group of 16 friends, the house was perfect, nothing was missing. Nice accommodations very clean, housekeeping every day. Unforgettable breakfa
…see more

from £482 / night

£3372 - £4395 / week

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Responds fast!
avg. 3 hours 22 minutes

from £482 / 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 £467 / night

£2543 - £4238 / week

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from £467 / night

(11) Excellent 

40

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £170 / night

£1187 - £1736 / week

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Responds fast!
avg. 3 hours 22 minutes

from £170 / 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 £231 / night

£1611 - £2039 / week

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from £231 / night

(6) Excellent 

31

Holiday villa in Costalpino

Siena / Costalpino

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Private garden
“Belvedere e stupendo” After a beautifully green, bus ride from Rome, I arrived at my designated stop a few kilometer’s before Siena and waited for my transfer to Belvedere, a magical home at the end of a beautiful long winding driveway where views of
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from £191 / night

£1272 - £1653 / week

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Responds fast!
avg. 3 hours 10 minutes

from £191 / night

100

Holiday villa with swimming pool in Moltacino

Province of Siena / Moltacino

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £267 / night

£1865 - £3560 / week

Enquire View

from £267 / 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 £334 / night

£2331 - £3814 / week

Enquire View

from £334 / night

100

Gaiole in Chianti holiday villa rental

Province of Siena / Gaiole in Chianti

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

from £390 / night

£2712 - £3814 / week

Enquire View

from £390 / night

(1) Excellent 

99

Province of Siena / San Gimignano

1 4 Min stay varies

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

from £106 / night

£653 - £975 / week

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from £106 / night

24

Celle sul Rigo holiday villa rental

San Casciano dei Bagni / Celle sul Rigo

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £194 / night

£1356 - £2434 / week

Enquire View

Responds fast!
avg. 27 minutes

from £194 / night

19

Holiday villa in Pienza

Province of Siena / Pienza

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £155 / night

£1085 - £2034 / week

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from £155 / night

(43) Excellent 

39

Holiday villa in Siena

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Perfect villa in perfect location” I need to start to say thank you to Jacopo and Fabio that made our holiday and stay absolutely perfect. They were both so helpful and such a pleasure to liaise with, even if we arrived later than expected! The
…see more

from £237 / night

£1526 - £3560 / week

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from £237 / night

(1) Excellent 

32

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 £249 / night

£1739 - £2492 / week

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Responds fast!
avg. 3 hours 22 minutes

from £249 / night

22

Villa rental in San Giovanni d'Asso with swimming pool

Province of Siena / San Giovanni d'Asso

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £686 / night

£4800 - £5850 / week

Enquire View

from £686 / night

28

Sinalunga holiday villa rental

Province of Siena / Sinalunga

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £119 / night

£832 - £1614 / week

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from £119 / 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 £387 / night

£2318 - £4003 / week

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Responds fast!
avg. 3 hours 28 minutes

from £387 / night

(1) Excellent 

23

Holiday villa with shared pool in Montepulciano

Province of Siena / Montepulciano

4 2 Min stay varies

  • 4 bedrooms
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Ask owner if suitable for children
“Old-world Italian charm in a beautiful Tuscan setting” It's a job to find it it, but once you do, you'll want to stay longer than you've booked for. The house has been in the family since 1812 - they produce their own wine - and Olimpia is a charming
…see more

from £30 / night

£208 / week

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Responds fast!
avg. 1 hour 50 minutes

from £30 / night

(3) Excellent 

36

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

from £219 / night

£1477 - £4133 / week

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from £219 / night

6

Province of Siena / Montepulciano

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Private garden

from £145 / night

£848 / week

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from £145 / night

29

Province of Siena / Rapolano Terme

3 6 1 night min

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

from £85 / night

£551 / week

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from £85 / night

(12) Very Good 

28

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

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 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 £140 / night

£975 - £2034 / week

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from £140 / night

22

Holiday villa rental

Colle di Val d'Elsa / Campiglia dei Foci

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £119 / night

£2077 - £2543 / week

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from £119 / 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 £339 / night

£1950 - £3390 / week

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from £339 / night

20

Province of Siena / Chiusdino

6 12 2 nights min

  • 6 bedrooms
  • Sleeps 12
  • 2 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £678 / night

£3221 / week

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from £678 / night

24

Holiday villa with swimming pool in Macciano

Chiusi / Macciano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £154 / night

£1073 - £1895 / week

Enquire View

Responds fast!
avg. 27 minutes

from £154 / night

22

Holiday villa rental

Province of Siena / Pienza

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £291 / night

£2034 - £3306 / week

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from £291 / night

(1) Excellent 

12

Province of Siena / Siena

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Private garden

from £128 / night

£831 / week

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from £128 / night

33

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 £128 / night

£890 / week

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Responds fast!
avg. 2 hours 36 minutes

from £128 / night

(2) Excellent 

39

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A charming Tuscan farmhouse villa” We stayed here for a most enjoyable week in September 2016. It is all that the owner Giada describes and she is a charming and helpful host. The villa, a converted stone farmhouse, is located on the outskirts of Sien
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from £128 / night

£1000 - £2204 / week

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from £128 / night

(6) Excellent 

23

Ski villa to rent in Piancastagnaio

Province of Siena / Piancastagnaio

3 12 2 nights min

  • 3 bedrooms
  • Sleeps 12
  • 2 nights min
  • Ski
  • Child friendly
  • Pet friendly

from £97 / night

£500 - £1030 / week

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Responds fast!
avg. 1 hour 17 minutes

from £97 / night

(2) Excellent 

24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £194 / night

£1356 - £3389 / week

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from £194 / night

16

Province of Siena / Castellina In Chianti

3 6 7 nights min

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

from £194 / night

£1177 / week

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Responds fast!
avg. 56 minutes

from £194 / night

24

Holiday villa rental

Castelnuovo Berardenga / Vagliagli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £197 / night

£1377 - £2087 / week

Enquire View

Responds fast!
avg. 27 minutes

from £197 / night

1