Short city breaks Province of Siena

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Province of Siena

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589 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.

(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

 …see more

from £62 / night

£404 - £851 / week

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from £62 / 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
Tenuta di Argiano a Montepulciano, located near MONTEPULCIANO, is surrounded by vineyards growing grapes for the famous local wines, Vino Nobile di Montepulciano and Rosso di Montepulciano, and is peaceful and quite. swimming pool and wifi . bikes tour, spa nearby, It  …see more

from £60 / night

£418 / week

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from £60 / night

(4) Excellent 

28

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
'Podere Collinella' has been re-built to a high standard, retaining the charm of a Tuscan farmhouse.The walls are of the old stone, chestnut beams support the ceiling, and positioned on a slight hill has wonderful views of the surrounding countryside. Podere C  …see more

from £71 / night

£483 - £606 / week

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from £71 / night

Featured properties

(1) Excellent 

13

Province of Siena / San Giovanni d'Asso

2 4 5 nights min

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

 …see more

from £79 / night

£527 - £571 / week

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from £79 / 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 £53 / night

£308 - £527 / week

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from £53 / night

35

Holiday villa with swimming pool in Castelmuzio

Province of Siena / Castelmuzio

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
When Eric and Kathy decided they wanted to settle in Tuscany and provide people with the sort of holidays they themselves had always dreamed of - but had rarely been able to find - they knew they had found the ideal property in Castelmuzio for many reasons, amongst whic  …see more

from £439 / night

£3071 - £4167 / week

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from £439 / night

(2) Excellent 

34

Radda in Chianti holiday farmhouse rental

Province of Siena / Radda in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Pet friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce organic Chianti Classico wine and extra virgin olive oil.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £53 / night

£281 - £404 / week

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from £53 / night

7

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets

 …see more

from £71 / night

£483 - £729 / week

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from £71 / 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

 …see more

from £49 / night

£316 - £514 / week

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from £49 / night

31

Province of Siena / Monticiano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 50 km
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £62 / night

£395 - £422 / week

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from £62 / night

(18) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 170 km
  • Child friendly
  • Car not necessary
“Well maintained apartment and very helpful owner” Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and  …see more

from £105 / night

£614 - £1043 / week

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from £105 / night

(10) Excellent 

26

Province of Siena / Montepulciano

2 4 Min stay varies

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

 …see more

from £75 / night

£544 - £755 / week

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from £75 / night

(1) Excellent 

13

Province of Siena / Chianciano Terme

2 3 2 nights min

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

 …see more

from £40 / night

£264 / week

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from £40 / night

(9) Very Good 

6

Montepulciano / Valiano

1 2 1 night min

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

 …see more

from £44 / night

£308 / week

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from £44 / night

(11) Excellent 

25

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
In the deep core of old part of Montepulciano, quiet and in the middle of of streets of monuments, art shops, restaurants and wine shops and cellars.  …see more

from £79 / night

£368 - £465 / week

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from £79 / night

17

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

 …see more

from £84 / night

£430 - £1000 / week

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from £84 / night

19

Siena / Gracciano di Colle Val d'Elsa

2 4 Min stay varies

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

 …see more

from £62 / night

£658 - £922 / week

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from £62 / night

(11) Excellent 

27

Holiday cottage with swimming pool, golf nearby in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“A lovely villa in beautiful surroundings.” We have recently returned from our first holiday in Tuscany with our two young sons and all agree that we will return to this area again. The villa although a short drive into Casole was situated amongst oli  …see more

from £118 / night

£702 - £1009 / week

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from £118 / 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

 …see more

from £79 / night

£553 / week

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from £79 / night

4

Province of Siena / Chiusi

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

Pricing unknown

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Pricing unknown

(3) Excellent 

24

Province of Siena / Castiglione D'Orcia

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Pet friendly

 …see more

from £47 / night

£331 - £492 / week

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from £47 / 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

 …see more

from £106 / night

£737 / week

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from £106 / night

(25) Excellent 

18

Holiday apartment in Siena

Province of Siena / Siena

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
“This is an excellent apartment in the centre of Sienna.” This is a great apartment as is shown by the photos. It is a little difficult to find the first time but once located the task was simple. We found overnight car parking 10 minutes away for a c  …see more

from £136 / night

£886 - £1996 / week

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from £136 / 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
Green apartment Siena centre-Central, ground floor, easy accessible, cosy, tastefully furnished. Double bedroom, fully equipped kitchen with sofa bed for two guests, large bathroom with shower, free WIFI, sat Tv, air conditioning.<br />Upon request as extra servic  …see more

from £39 / night

£271 / week

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from £39 / 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 - £2153 / week

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from £114 / night

(1) Excellent 

10

Province of Siena / San Gimignano

2 4 1 night min

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

 …see more

from £58 / night

£400 / week

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from £58 / 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

 …see more

from £255 / night

£1404 - £2018 / week

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from £255 / night

8

Province of Siena / Cetona

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Private garden

 …see more

from £259 / night

£1799 / week

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from £259 / night

5

Province of Siena / Pienza

2 4 Min stay varies

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

 …see more

from £123 / night

£588 - £922 / week

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from £123 / night

(1) Very Good 

36

Province of Siena / Siena

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Child friendly
  • Car not necessary

 …see more

from £79 / night

£553 / week

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from £79 / 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

 …see more

from £52 / night

£351 - £572 / week

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from £52 / night

(8) Very Good 

5

Apartment rental in Siena

Province of Siena / Siena

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 105 km
  • Car not necessary
  • Air conditioning
Best views of Siena.The apartment being only a few minutes from the Campo. The terrace is magnificent with 360°panoramic views of the centre of town, Duomo,the bell tower.It's very quite and you can relax on the roof deck taking a sunbath on the long chair.&  …see more

from £115 / night

£983 / week

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from £115 / night

13

Holiday chalet in Valiano

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Apartment with living-dining area, kitchen corner , double bedroom , bathroom with shower. TV SAT, iron and iron board, freezer, oven, high chair.  …see more

from £106 / night

£746 / week

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from £106 / night

15

Province of Siena / Pienza

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £193 / night

£720 - £1141 / week

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from £193 / night

18

Holiday apartment in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 85 km
  • Child friendly
  • Car not necessary
Brown apartment Central and cosy apartment with double bedroom, bathroom with shower, large living area with sofa bed, equipped kitchen, private equipped garden, free WIFI, TV, air conditioning.<br />Upon request as extra services: cooking classes, wine tours, e  …see more

from £43 / night

£301 / week

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from £43 / 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
“Perfect holiday location” Our family group of 8 adults spent 5 nights at Villa LisiDor - a perfect location for both relaxing & a great base for exploring the local region. The roads in Chianti can be narrow & windy but worth the drive to villages lik  …see more

from £416 / night

£2908 - £4474 / week

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from £416 / night

24

Province of Siena / San Quirico d'Orcia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £123 / night

£860 / week

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from £123 / 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

£492 - £553 / week

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from £79 / 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
Villa Ardene provides its guests with high level services in a magical, peaceful and unforgettable atmosphere. All the suites and apartments are equipped with whirlpool bath, air conditioning, satellite TV, internet connection.The interior space in “arte p  …see more

from £565 / night

£3948 - £6878 / week

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from £565 / night

(1) Excellent 

35

Holiday apartment in Radicondoli

Province of Siena / Radicondoli

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Child friendly
Il Noce is a very comfortable recently renovated apartment and is ideal for a quiet or active holiday in the idyllic countryside with splendid views and inviting walks. This attractive self contained apartment adjoins the main farmhouse where the owners live and has tw  …see more

from £88 / night

£615 / week

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from £88 / night