Holiday rentals in Province of Siena: Villas, Cottages and Apartments

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4,070 Holiday homes

14

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Car not necessary

 …see more

from £69 / night

£483 / week

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from £69 / night

24

Tuscany Villa with pool, Walking Distance to Town - Castelmuzio villa sleeps 11

Province of Siena / Castelmuzio

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
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 £367 / night

£2565 - £4095 / week

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from £367 / night

10

Province of Siena / Rapolano Terme

2 5 Min stay varies

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

 …see more

from £87 / night

£604 - £725 / week

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from £87 / night

(1) Very Good 

14

Villa Il Poggino - Buonconvento villa sleeps 13

Province of Siena / Buonconvento

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Beautiful villa in a fully renovated typical Sienese farmhouse. The renovation was completed in 2007. The villa is 1.5 km from Ponte d'Arbia, a little village with a bar, restaurant, grocery shop and butcher. Buonconvento is 6 km away and offers a broader selection of s  …see more

from £308 / night

£2156 - £3966 / week

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from £308 / night

21

Asciano SI - ITS153 - Asciano villa sleeps 2

Province of Siena / Asciano

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
Situated in Siena this grand home is the perfect place to delight and discover the Tuscan countryside. 1 double bed and 1 bathroom makes this place the perfect abode for a couple. A swimming pool is located at the house. Throughout the holiday home various amenities  …see more

from £42 / night

£293 - £638 / week

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from £42 / night

24

wonderful hamlet apartments -Seve - San Giovanni d'Asso apartment sleeps 4

Province of Siena / San Giovanni d'Asso

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
This charming old hamlet is located at 5 km from San Giovanni d'Asso, in the heart of the Crete Senesi, at just 13 km from Pienza and 16 km from Montalcino. The estate belonged for six hundred years to the notorious Piccolomini family, a protagonist of Italian Ren  …see more

from £155 / night

£1081 / week

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from £155 / night

20

Castle Farm Villa (v053) - Cetona villa sleeps 10

Province of Siena / Cetona

1 10 Min stay varies

  • 1 bedroom
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful stone built villa made up of:On the ground floor there is a large living room with fireplace with doors on to the garden, dining room with access to the garden, a large kitchen with fireplace and access on to the portico set with table and chairs, a twin bedro  …see more

from £255 / night

£1785 - £2500 / week

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from £255 / night

8

Fattoria il Musarone - Aliseo. Sinalunga - Sinalunga apartment sleeps 6

Province of Siena / Sinalunga

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 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 £69 / night

£475 - £880 / week

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from £69 / night

11

Province of Siena / Radicondoli

1 3 2 nights min

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

 …see more

from £50 / night

£432 / week

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from £50 / night

33

Asciano / Chiusure

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £238 / night

£1660 / week

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from £238 / night

100

La Fiorita - Lavanda - Vergelle apartment sleeps 6

Province of Siena / Vergelle

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Lavanda is a cozy apartment decorated with a rustic style. The apartment is located on the first floor and it enjoys great views of the town of Cortona and the Valdichiana Valley. The apartment has a fully equipped kitchen with dishwasher. The living room has a comforta  …see more

from £121 / night

£587 - £863 / week

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from £121 / night

25

Borgo 7 Tigli #3 - Montepulciano apartment sleeps 6

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Borgo 7 Tigli #3 is a splendid apartment with two bedrooms and two bathrooms which is part of a property with a total of 6 apartments sharing a pool. Located in the magnificent atmosphere of the hills surrounding the ancient town of Montepulciano, famous for its histo  …see more

from £100 / night

£647 - £854 / week

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from £100 / night

4

villa di campagna - Chiusdino villa sleeps 6

Province of Siena / Chiusdino

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Private garden
Appartamenti Vacanze a ChiusdinoIl comune di Chiusdino, paese natale di San Galgano, dista circa 40 chilometri da Siena ed è immerso nella natura incontaminata della Val di Merse regione d'Italia. Chiusdino è un ottimo punto di partenza per esplorare la regione e  …see more

from £78 / night

£518 / week

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from £78 / night

20

Bandita - 26120001 - Guazzino farmhouse sleeps 20

Sinalunga / Guazzino

11 20 Min stay varies

  • 11 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful villa dating back to the 18th century composed by a “Leopold style” farmhouse and 3 barns accurately restored for creating a unique complex and situated on the top of a hill in absolutely quiet position with panoramic views on the surrounding countryside.  …see more

from £831 / night

£4847 - £7261 / week

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from £831 / night

100

Pienza 44315 - Pienza villa sleeps 14

Province of Siena / Pienza

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate units rent  …see more

from £336 / night

£2351 - £6792 / week

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from £336 / night

14

Monteroni d'Arbia Villa - Monteroni d'Arbia villa sleeps 14

Province of Siena / Monteroni d'Arbia

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This detached house with private garden and pool inside an agricultural business cultivated with olive trees, features also a park and views of Siena and is set in the beautiful Sienese countryside, just 3 km from Vescovado and 5 km from Monteroni away. It consists of t  …see more

from £444 / night

£3104 / week

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from £444 / night

9

La Francigena B&B - Staggia Senese apartment sleeps 7

Poggibonsi / Staggia Senese

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 73 km
  • Swimming pool
  • Child friendly
Francigena is a holiday house located in the heart of Tuscany, in a crucial area. From here you can easily reach several points of artistic and cultural interest of the region.The building - dating back to the second half of the 18th century - is composed of one bedroom  …see more

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Pricing unknown

32

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets

 …see more

from £69 / night

£388 - £432 / week

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from £69 / night

18

59736001 - Castellina In Chian - Castellina In Chianti farmhouse sleeps 4

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone Tuscan hamlet dating back to the 16th century comprising 8 accommodations and nestling deep among the splendid Chianti Classico vineyards. This property still shows the blazon of the astronomer Galileo Galilei who stayed in this hamlet many years and dre  …see more

from £116 / night

£680 - £1139 / week

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from £116 / night

20

Castelnuovo Berardenga / Pianella

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £528 / night

£3693 - £5654 / week

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from £528 / night

13

Fiorello - Amorosa apartment sleeps 4

Sinalunga / Amorosa

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
....is an ancient farm of the eighteenth century,renovated in Tuscany style in place which are nice apartments in a wonderful park,located in the heart of the Siena countryside,situated on a hill between Val di Chiana, Crete and the Val d'Orcia .Surrounded by woods  …see more

from £100 / night

£690 / week

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from £100 / night

10

Province of Siena / San Casciano dei Bagni

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £59 / night

£345 / week

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from £59 / night

12

Siena / Costalpino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £44 / night

£285 - £388 / week

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from £44 / night

20

Chiusi - 42398003 - Province of Siena farmhouse sleeps 12

Tuscany / Province of Siena

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Podere Sionne is ideal for families and groups of friends, and anyone who loves a relaxing holiday surrounded by nature, wine and tasty food, thermal baths, escurtions to Etruscan area, or just going around to many nice towns traveling in the magnificent landscapes of t  …see more

from £219 / night

£1397 - £1659 / week

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from £219 / night

12

Province of Siena / Montalcino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

 …see more

from £104 / night

£690 / week

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from £104 / night

30

Province of Siena / Sinalunga

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £95 / night

£500 / week

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from £95 / night

(1) Excellent 

13

La casella, podere Capannacce Horse Farm - Crete Senesi farmhouse sleeps 2

Asciano / Crete Senesi

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
In the Crete Senesi, in the heart of a working organic farm, apartment converted from a traditional farm with a total of 2 beds, is a welcoming and witty, surrounded by a unique landscape. 60 sqm.The Accommodation The atmosphere and perhaps access to the garden house  …see more

from £65 / night

£302 / week

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from £65 / night

12

Il Baroncino - I Carri - Sovicille apartment sleeps 4

Province of Siena / Sovicille

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
Il Baroncino stands alone among the rolling hills, in 8 hectares of private land, with many age-old chestnut and oak trees. It is a large country house with several smaller adjacent buildings, such as the former chestnut barn, the wood store and a hay barn. All in all,  …see more

from £92 / night

£638 - £914 / week

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from £92 / night

21

Borgo 7 Tigli #7 - Montepulciano apartment sleeps 4

Province of Siena / Montepulciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Borgo 7 Tigli #7 is a splendid apartment with one bedroom and one bathroom which is part of a property with a total of 6 apartments sharing a pool. Located in the magnificent atmosphere of the hills surrounding the ancient town of Montepulciano, famous for its history  …see more

from £69 / night

£423 - £630 / week

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from £69 / night

17

Province of Siena / Torrita di Siena

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from £138 / night

£854 / week

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from £138 / night

8

Siena / Caprera

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min

 …see more

from £87 / night

£561 / week

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from £87 / night

19

APARTMENT GIRASOLI 2205 - Casaglia apartment sleeps 3

San Gimignano / Casaglia

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Pet friendly
Girasole is a very cozy apartment, located on the ground floor of the main villa, with independent entrance.It is comprised of a double bedroom (with king size bed ), bathroom with shower stall and a kitchen / living room with direct access to a private outdoor dining a  …see more

from £84 / night

£544 / week

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from £84 / night

20

APARTMENT COLOMBAIA 2301 - Rapolano Terme apartment sleeps 2

Province of Siena / Rapolano Terme

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Double room with double bed, living room with kitchenette, bathroom, private terrace. Heating, satellite-TV. Furnished with antique pieces of furniture. Ground floor. Private terrace.- Villa Buoninsegna is a big agricultural property with 320 hectares and a few apartmen  …see more

from £79 / night

£550 / week

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from £79 / night

100

Montefollonico - Province of Siena villa sleeps 8

Tuscany / Province of Siena

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
ExteriorThis stunning farmhouse is conveniently located with just a walking distance away from the small village of Montefollonico, close distance to the well known wine town of Montepulciano. The village of Montefollonico is known for its top-notch restaurants that hav  …see more

from £567 / night

£3966 - £4569 / week

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from £567 / night

20

Province of Siena / Le Piazze

1 4 Min stay varies

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

 …see more

from £87 / night

£378 - £479 / week

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from £87 / night

13

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

 …see more

from £233 / night

£1630 / week

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from £233 / night

18

San Gimignano / Ulignano

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £113 / night

£768 / week

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from £113 / night

14

Holidayhome Casa Eolo, Borgo San Vincenti, Tuscany - Gaiole in Chianti house sleeps 4

Province of Siena / Gaiole in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Casa Eolo is immersed in the most idyllic Chiantishire: surrounded by vineyards producing world-class red wine, overlooking the rolling hills of Tuscany and is located in the village of San Vincenti, with its stone houses and clay roof tiles. The village has been comple  …see more

from £95 / night

£664 - £966 / week

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from £95 / night

100

Montefollonico 65998 - Pienza villa sleeps 10

Province of Siena / Pienza

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Large Tuscan farmhouse dating back to the 15trh century built on the ruins of an ancient convent of the year 1200. This property with a charming inner courtyard, is situated in quiet and panoramic location on a large 100-hectare estate producing olive oil and wine. This  …see more

from £427 / night

£2494 - £3414 / week

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from £427 / night

11

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly

 …see more

from £69 / night

£414 / week

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from £69 / night

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