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Province of Siena

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2,131 Holiday homes

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

(15) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Very comfortable home away from home” Casacorvo Minore is a very comfortable apartment well located in the heart of Chianti. It has great views from its veranda which fostered perfect starts for each day as we had breakfast sitting in the morning sun.  …see more

from £100 / night

£560 - £760 / week

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from £100 / 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  …see more

from £131 / night

£870 - £2000 / week

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from £131 / night

(26) Excellent 

28

Holiday apartment in Montisi

Province of Siena / Montisi

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+

from £122 / night

£783 / week

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from £122 / night

(8) Very Good 

14

Apartment rental in Siena

Province of Siena / Siena

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Car not necessary

from £114 / night

£974 / week

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from £114 / night

(13) Excellent 

20

Montalcino / Sant'Angelo in Colle

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 68 km
  • Suitable for children age 5+
  • Private garden

from £66 / night

£392 - £757 / week

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from £66 / night

(18) Excellent 

43

Holiday apartment in Monticchiello

Pienza / Monticchiello

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £66 / night

£322 - £785 / week

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from £66 / night

(3) Excellent 

26

Holiday apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Ask about pets
“Excellent base for chilling and siteseeing/citytrips” We had a great time at Elena's place! The appartement was clean, big, safe and modern. We used our own kitchen to cook our food. We stayed a week longer then planned. It is a very good base to go b  …see more

from £79 / night

£314 - £487 / week

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from £79 / night

55

Province of Siena / Cetona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from £105 / night

£609 - £740 / week

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from £105 / night

(3) Excellent 

28

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £35 / night

£244 - £835 / week

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from £35 / night

(42) Excellent 

19

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
“Stunning accommodation in a fabulous location” Amazing apartment with everything you could need for a reaching haven after a busy day of sight seeing. The views are like paintings and the gardens are beautiful. Mary- Ann is a fabulous host, we had an  …see more

from £194 / night

£1049 - £1533 / week

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from £194 / night

(8) Excellent 

31

Province of Siena / Siena

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Pet friendly

from £105 / night

£731 / week

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from £105 / night

(30) Excellent 

20

Holiday apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly

from £70 / night

£418 - £583 / week

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from £70 / night

(4) Excellent 

19

Holiday farmhouse with swimming pool in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Farm estate living in Tuscany is pretty special, truly a unforgettable place to stay with fantastic owners” Great place to stay to truly get away and enjoy the relaxing Tuscany life. The chef at home was fantastic and the local shopping 5-10 minutes a  …see more

from £209 / night

£783 - £2192 / week

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from £209 / night

34

Sant'Albino holiday villa rental

Montepulciano / Sant'Albino

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly

from £398 / night

£2783 - £5392 / week

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from £398 / night

(1) Very Good 

23

San Gimignano / Ulignano

2 6 Min stay varies

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

from £105 / night

£609 - £957 / week

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from £105 / night

(1) 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 £342 / night

£2392 - £3914 / week

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from £342 / night

25

Pienza holiday lodge rental

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Air conditioning

from £74 / night

£518 - £822 / week

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from £74 / 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 £160 / night

£1114 - £2087 / week

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from £160 / night

(3) Excellent 

28

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 7 7 nights min

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

from £37 / night

£253 - £861 / week

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from £37 / night

4

Holiday apartment in San Fabiano

Monteroni d'Arbia / San Fabiano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £131 / night

£696 - £1044 / week

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from £131 / night

(11) Very Good 

32

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Excellent value Tuscan villa in a lovely setting” We stayed in the Agrifolo apartment at Le Fontanelle in May 2015. I was visited with my partner and my parents as we treated them to a Tuscan trip to start the summer. The villa was lovely - simple  …see more

from £61 / night

£461 - £822 / week

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from £61 / night

(5) 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  …see more

from £196 / night

£1305 - £1696 / week

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from £196 / night

(6) Very Good 

25

Province of Siena / Monteriggioni

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £48 / night

£314 - £509 / week

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from £48 / night

23

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £224 / night

£1566 - £3131 / week

Enquire View

from £224 / night

(6) Very Good 

40

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 £174 / night

£931 - £2348 / week

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from £174 / night

(1) Excellent 

27

Holiday barn with swimming pool in Quercegrossa

Monteriggioni / Quercegrossa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £74 / night

£453 - £879 / week

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from £74 / night

21

Holiday apartment in Siena

Province of Siena / Siena

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Child friendly
  • Car not necessary

from £105 / night

£731 / week

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from £105 / night

20

Holiday farmhouse rental

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Nearest beach 44 km
  • Swimming pool
  • Child friendly

from £358 / night

£2505 - £6453 / week

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from £358 / night

(1) Excellent 

8

Province of Siena / Strove

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Private garden

from £44 / night

£305 / week

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from £44 / night

(6) Very Good 

45

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £79 / night

£479 - £505 / week

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from £79 / night

(2) Excellent 

31

Holiday apartment in Cetona

Province of Siena / Cetona

2 4 6 nights min

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

from £53 / night

£348 / week

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from £53 / night

(5) Excellent 

23

Holiday apartment in Pienza

Province of Siena / Pienza

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
“Fantastic place - great selection of restaurants” Truly a maginificent apartment exceeding our expectations - really nice to cool down in the jacuzzi overlooking Montalcino when the weather was at its hottest ! Also very convenient with regards to  …see more

from £122 / night

£853 / week

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from £122 / night

(3) Excellent 

18

Montalcino holiday studio rental

Province of Siena / Montalcino

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £127 / night

£840 / week

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from £127 / night

(6) Excellent 

35

Monticiano / Tocchi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 50 km
  • Child friendly
  • Pet friendly

from £61 / night

£400 - £844 / week

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from £61 / night

21

Holiday b&b in Acquaviva di Montepulciano

Montepulciano / Acquaviva di Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £60 / night

£414 / week

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from £60 / 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

(4) Excellent 

31

Province of Siena / Murlo

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £70 / night

£421 - £500 / week

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from £70 / 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 £412 / night

£2883 - £4435 / week

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from £412 / night

(4) Excellent 

17

Holiday home in Cetona

Province of Siena / Cetona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about pets
“A real tase of Tuscany” If you're looking for an authentic old town stay then you'll be very happy. Great location in the old town and so close to lots small towns to explore. Train to Florence as a day trip. Large rooms cumfy beds and amazing views f  …see more

from £61 / night

£427 / week

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from £61 / night

(1) Excellent 

12

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

from £44 / night

£305 / week

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from £44 / night