Short city breaks Province of Siena

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Province of Siena

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590 Holiday homes

Filters applied: City breaks

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

(3) Excellent 

16

Province of Siena / Casole d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 km
  • Child friendly

from £40 / night

£274 / week

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from £40 / night

(16) Very Good 

27

Holiday apartment in Sant Andrea a Montecchio

Siena / Sant Andrea a Montecchio

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Car not necessary
“Reality of a dream!” I was looking for a quiet week with a beautiful panorama not far from Siena, to enjoy after the Palio and before participating in an intensive celebration later in July within Siena. I studied the information on Sant'Andrea a Mon  …see more

from £61 / night

£348 - £522 / week

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from £61 / night

(22) Excellent 

60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

 …see more

from £48 / night

£292 - £422 / week

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from £48 / 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

(9) Very Good 

6

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Pet friendly

from £44 / night

£305 / week

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from £44 / 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 £122 / night

£2131 - £2609 / week

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from £122 / night

24

Castelnuovo Berardenga / Pievasciata

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly

from £53 / night

£274 / week

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from £53 / night

(2) Excellent 

18

Province of Siena / Gaiole in Chianti

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

from £79 / night

£548 / week

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from £79 / 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

15

Holiday townhouse in Pienza

Province of Siena / Pienza

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 100 km
  • Child friendly
  • Car not necessary

from £109 / night

£761 - £979 / week

Enquire View

from £109 / 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  …see more

from £114 / night

£766 - £2261 / week

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from £114 / night

(15) Excellent 

23

Castelnuovo Berardenga holiday apartment rental

Province of Siena / Castelnuovo Berardenga

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“We enjoyed our holidays in this beautiful agriturismo” We have spent two weeks in Fernando Mattii's agriturismo. The site is very clean and very well maintained. Fernando Mattii was always helpful when we needed anything and he even brought us some wo  …see more

from £131 / night

£914 / week

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from £131 / night

(6) Excellent 

37

Torrita di Siena / Montefollonico

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Air conditioning

from £105 / night

£1131 - £2044 / week

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from £105 / night

(1) Excellent 

24

Province of Siena / Sarteano

4 9 1 night min

  • 4 bedrooms
  • Sleeps 9
  • 1 night min
  • Nearest beach 120 km
  • Child friendly
  • Private garden

from £44 / night

£305 / week

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from £44 / night

22

Holiday apartment with swimming pool in Crete Senesi

Asciano / Crete Senesi

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £105 / night

£731 / week

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from £105 / night

16

Holiday home rental

Province of Siena / Siena

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

from £218 / night

£1522 / week

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from £218 / 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

(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

(11) Excellent 

19

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
  • Pet friendly
“Wonderful, Wonderful, Highly Recommended.” My wife and I stayed 23rd. June - 5th. July 2013, and had a wonderful holiday. So relaxing and no hassle whatsoever. The farmhouse has three one bedroomed apartments available and a fourth which Elena (the  …see more

from £79 / night

£487 - £548 / week

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from £79 / night

33

Murlo / Casciano di Murlo

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning

from £53 / night

£314 / week

Book View

from £53 / night

13

Province of Siena / Pievescola

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £53 / night

£348 / week

Book View

from £53 / night

(4) Very Good 

16

Radicofani / Contignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Child friendly
  • Pet friendly

from £70 / night

£348 / week

Book View

from £70 / night

(4) Very Good 

19

Province of Siena / Sovicille

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £61 / night

£427 / week

Book View

from £61 / night

(1) Excellent 

21

Province of Siena / San Casciano dei Bagni

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly

from £53 / night

£392 - £940 / week

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from £53 / night

(1) Excellent 

20

Caprera holiday apartment rental

Siena / Caprera

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning

from £70 / night

£435 - £479 / week

Book View

from £70 / night

(9) Very Good 

41

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
“Stunning Views” We had a most enjoyable time at this house and would recommend it for its location and closeness to Montepulciano. The house was delightful and the views across the valley and surrounding countryside were excellent. We can recommend  …see more

from £100 / night

£500 - £895 / week

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from £100 / 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

(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

(1) Excellent 

29

Province of Siena / Montepulciano

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £253 / night

£1392 - £2000 / week

Book View

from £253 / night

(7) Very Good 

22

Province of Siena / Montepulciano

2 6 3 nights min

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

from £79 / night

£461 / week

Book View

from £79 / night

(3) 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 £257 / night

£1087 - £2305 / week

Book View

from £257 / 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

Book View

from £61 / night

34

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £61 / night

£366 - £705 / week

Book View

from £61 / night

(8) Excellent 

56

Province of Siena / Siena

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

from £47 / night

£653 - £1109 / week

Book View

from £47 / night

36

Radicofani / Contignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

from £61 / night

£435 / week

Book View

from £61 / night

27

Holiday villa in Monteriggioni

Province of Siena / Monteriggioni

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly

from £99 / night

£687 - £1061 / week

Book View

from £99 / night

(6) Excellent 

56

Holiday guest house in Siena

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning

from £392 / night

£2392 / week

Book View

from £392 / night

29

Siena holiday apartment rental

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £118 / night

£822 / week

Book View

from £118 / 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 £243 / night

£1566 - £3653 / week

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from £243 / 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

Book View

from £122 / night

1