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Province of Siena

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1,722 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.

(2) Excellent 

41

Province of Siena / Cetona

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 28 km
  • Swimming pool

 …see more

from £300 / night

£2095 / week

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from £300 / night

(2)  

30

Province of Siena / Castellina In Chianti

2 6 Min stay varies

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

 …see more

from £119 / night

£470 - £709 / week

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from £119 / 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
Cottage with large garden, three bedrooms with 10 + 2 beds, kitchen, living room, tree bathrooms. Possibility of horse riding in the Monte Amiata's woods, even all day long. It has satellite TV, internet connection, Wi-Fi, small inflatable heated pool. Located i  …see more

from £99 / night

£509 - £1048 / week

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from £99 / night

Featured properties

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
Villa Nr. San Gimignano, Siena Province, Tuscany, Italy Typical Tuscan Style Villa with Private Pool and Large Private garden. 12.000 Square Metres Of Gardens, With Pine Trees, Monumental Oaks And Olive Grove Wonderful stone building situated in a peaceful position wit  …see more

from £137 / night

£1496 - £2565 / week

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from £137 / night

(2) Very Good 

29

Holiday farmhouse with shared pool in Torri

Sovicille / Torri

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Free wifi connection; free bikes, swimming pool, terraces, panoramic landscapes, free washing machine  …see more

from £95 / night

£1069 - £1212 / week

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from £95 / 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 £571 / night

£4000 - £5214 / week

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from £571 / night

15

Holiday farmhouse accommodation

Province of Siena / Cetona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Typical Italian agritourism with swimming pool.  …see more

from £130 / night

£906 - £1701 / week

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from £130 / night

28

Holiday apartment in Quercegrossa

Monteriggioni / Quercegrossa

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Villa is situated in a splendid 18th century mansion, with typical Sienese architecture. The property position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena (6 km away).The mansion is s  …see more

from £89 / night

£599 - £1616 / week

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from £89 / night

18

Holiday villa with swimming pool in Gracciano

Montepulciano / Gracciano

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Unique villa with swimming pool.  …see more

from £281 / night

£1966 - £2949 / week

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from £281 / night

(4) Excellent 

18

Farmhouse rental in Radicofani with shared pool

Province of Siena / Radicofani

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is furnished tastefully and with exclusive period furniture, fireplace, Sky TV, independent heating, external private space. Park, scenic swimming pool.  …see more

from £103 / night

£513 - £727 / week

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from £103 / night

(9) Excellent 

16

Holiday farmhouse in San Gimignano

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
House with two apartments near San Gimignano in TuscanyHoliday Apartment offers 2 flats inside an old barn that were recently restructured.Both the apartments can accommodate up to 4 people and are composed of a bedroom with bathroom, a small bedroom and a dinin  …see more

from £63 / night

£428 - £778 / week

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from £63 / night

20

Province of Siena / Castellina In Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

 …see more

from £107 / night

£748 / week

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from £107 / 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
The Agriturismo La Casetta nel Bosco is a beautiful, stone villa divided into two separate units which is part of an agritouristic Farm including olive groves, woods, several crops and a small-scale breeding of horses and ponies.  …see more

from £121 / night

£847 - £1642 / week

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from £121 / night

(5) Excellent 

39

Farmhouse rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £76 / night

£436 - £471 / week

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from £76 / night

(9) Excellent 

52

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

 …see more

from £120 / night

£727 / week

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from £120 / night

20

Holiday farmhouse with swimming pool in Iesa

Siena / Iesa

14 27 Min stay varies

  • 14 bedrooms
  • Sleeps 27
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa in Iesa with 14 bedrooms sleeps 27  …see more

from £3263 / night

£19038 - £25385 / week

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from £3263 / 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 £52 / night

£300 - £513 / week

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from £52 / night

100

Holiday villa with swimming pool in Montalcino

Province of Siena / Montalcino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
This villa provides guests with a panoramic pool, a living room, a fully equipped kitchen, a study room, four double bedrooms and three bathrooms.  …see more

from £513 / night

£3590 - £4872 / week

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from £513 / night

20

Holiday villa rental

Province of Siena / Radicofani

1 12 7 nights min

  • 1 bedroom
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This was an old monastery during the first half of the sixteenth century and went on to become a summer residence for the friars of Monte Oliveto Maggiore. It enjoys beautiful views across a valley. Old farmhouse, well restored, divided into three apartments.  …see more

from £179 / night

£1248 - £1932 / week

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from £179 / night

100

Holiday villa rental

Province of Siena / Montepulciano

5 13 7 nights min

  • 5 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
charming accommodation sleeps 13 people, so it is perfect for large families and is located in Tuscany Italy. This property is ideal if you seek a unique experience. The villa offers: a swimming Pool, a pet friendly space .  …see more

from £142 / night

£993 - £2201 / week

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from £142 / night

(12) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
“Beautiful views” An excellent, clean and very comfortable 2 bedroom apartment with two bathrooms (one with ensuite is down stairs), 3 minutes from Piazza Grande. The views are simply sensational. The owner Luca, is very attentive, showed us were to p  …see more

from £99 / night

£599 - £742 / week

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from £99 / 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
TinaiaGround Floor – large dining-living room, built-in kitchen, bathroom with shower, box room. First Floor – 1 master bedroom, 2 bedrooms with twin beds, 1 bathroom with bath, 1 bathroom with shower (one extra bed in the living room) area equipped for eati  …see more

from £116 / night

£808 / week

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from £116 / night

(2) Excellent 

24

Holiday apartment with shared pool in Monticchiello

Pienza / Monticchiello

3 7 5 nights min

  • 3 bedrooms
  • Sleeps 7
  • 5 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Casa Oriolo is an elegant apartment with 3 bedrooms and it is part of a small complex with 3 apartments total sharing a pool. Here you can enjoy a sojourn in contact with nature in a protected and uncontaminated oasis.The owners have carefully furnished the prop  …see more

from £153 / night

£1069 - £1667 / week

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from £153 / night

(2) Very Good 

29

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
.This charming accommodation lies in the countryside enjoying the most marvellous views of the undulating landscape and the towers of the city of San Gimignano only 3km away. It is a lovely location for enjoying country walks and relaxing<br />The pool and the gar  …see more

from £171 / night

£1197 - £1795 / week

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from £171 / night

(4) Excellent 

18

Province of Siena / Siena

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Private garden

 …see more

from £43 / night

£300 / week

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from £43 / 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 £69 / night

£471 - £590 / week

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from £69 / night

(14) Excellent 

24

San Gimignano holiday villa rental

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
“Beautiful!” Four of us stayed here in October 2012, the house is beautiful and immaculately maintained as are the gardens. Unfortunately the weather wasn't on our side so we didn't spend as much time in the garden as we'd have liked but you could spe  …see more

from £69 / night

£471 - £1539 / week

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from £69 / night

15

Holiday farmhouse rental

San Gimignano / Ulignano

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment in Volterra with 2 bedrooms sleeps 4  …see more

from £183 / night

£1277 - £1508 / week

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from £183 / night

(1) Very Good 

35

Province of Siena / San Gimignano

7 10 Min stay varies

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

 …see more

from £184 / night

£1283 - £2052 / week

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from £184 / night

(8) Excellent 

24

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic Villa and location shame about the weather” The villa was fantastic with extremely hospitable hosts. Grandma provided us with her fantastic home made cake and olive oil. Grandad provided us with home grown beans and lettuce. The Villa is sit  …see more

from £95 / night

£599 - £941 / week

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from £95 / night

(6) Excellent 

37

Torrita di Siena / Montefollonico

2 5 2 nights min

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

 …see more

from £103 / night

£1112 - £2009 / week

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from £103 / 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 £112 / night

£753 - £2206 / week

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from £112 / night

10

Holiday farmhouse in San Fabiano

Monteroni d'Arbia / San Fabiano

4 16 Min stay varies

  • 4 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The Podere Podernovo offers accommodation up to 16 people ,with all comforts,as heating, air conditioning, Internet,wi-fi, Tv with Sky.The Count Fiorentini will welcome you in his farmhouse just 12 km south of Siena in the Arbia valley. You can rent the whole Podere the  …see more

from £462 / night

£2565 - £3419 / week

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from £462 / night

(1) Average 

8

Sinalunga holiday apartment rental

Province of Siena / Sinalunga

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
In the heart of the countryside only 40 minutes from Siena five beautiful apartments have been made by restoring an old Tuscan country house set on a hillside with views all around. Each apartment retains its fascinating original characteristics. A courtyard around the  …see more

from £53 / night

£368 - £667 / week

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from £53 / night

100

Holiday villa with swimming pool in Province of Siena

Tuscany / Province of Siena

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Nearest beach 48 km
  • Swimming pool
  • Child friendly
Surrounded by natural woods and the most delightful quietness, this large villa sleeps up to 11 people and it offers an extended private garden with swimming pool, six bedrooms and exclusive amenities and comforts only 30km from Siena.  …see more

from £513 / night

£2180 - £3206 / week

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from £513 / night

(1) Excellent 

30

Province of Siena / San Gimignano

2 4 Min stay varies

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

 …see more

from £69 / night

£445 - £842 / week

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from £69 / night

26

Villa rental in Sant'Albino with swimming pool

Montepulciano / Sant'Albino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano. The property is situated in the heart a working farm with breathtaking views over the valley where Vino Nobile di Montepulciano is produced. The villa ha  …see more

from £257 / night

£1795 - £3077 / week

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from £257 / night

(2) Excellent 

22

Province of Siena / Castellina In Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly

 …see more

from £37 / night

£257 - £385 / week

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from £37 / night

23

Holiday villa accommodation

Province of Siena / Casole d'Elsa

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Lovely farmahouse with private garden & pool in Siena  …see more

from £153 / night

£1069 - £2265 / week

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from £153 / night

13

Province of Siena / San Gimignano

5 10 Min stay varies

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

 …see more

from £171 / night

£983 - £2821 / week

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from £171 / night