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

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Province of Siena

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4,196 Holiday homes

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

26

Montalcinello holiday home rental

Chiusdino / Montalcinello

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
It is plunged into the beautiful scenery of natural woods of Colline Metallifere 2 km far from the nearest village, where peacefulness is queen. About 30 km from Siena. The farmhouse has been recently restored according to the old structure with wood beams, fireplace,  …see more

from £310 / night

£1823 - £3178 / week

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from £310 / night

21

Holiday villa with shared pool in Asciano

Province of Siena / Asciano

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
This property in Tuscany Italy is a grand home that sleeps 2 people, so it is perfect for a couple. The accommodation offers a swimming pool and an internet connection.  …see more

from £42 / night

£289 - £628 / week

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from £42 / night

37

Holiday apartment with shared pool in Vagliagli

Castelnuovo Berardenga / Vagliagli

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Pet friendly
These holiday apartments in Tuscany are part of an estate situated in the Chianti Classico area, just 13 km from Siena, surrounded by vineyards and olive groves, in a peaceful place far from the traffic and bustle. The origins of the Castle date back to 1070, but follow  …see more

from £59 / night

£314 - £530 / week

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from £59 / night

Featured properties

4

Province of Siena / Pienza

1 2 1 night min

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

 …see more

from £60 / night

£331 / week

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from £60 / night

37

Province of Siena / Radicondoli

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Nearest beach 65 km
  • Child friendly
  • Ask about pets

 …see more

from £153 / night

£890 - £1128 / week

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from £153 / night

(2) Very Good 

34

Province of Siena / Castelnuovo Berardenga

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Air conditioning

 …see more

from £46 / night

£321 / week

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from £46 / night

4

Province of Siena / Siena

1 2 90 nights min

  • 1 bedroom
  • Sleeps 2
  • 90 nights min

 …see more

from £158 / night

£1102 / week

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from £158 / night

21

Holiday apartment in Siena

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
Delizioso appartamento situato poco fuori le mura di Siena, di fronte alle antiche Fonti di San Carlo. Appena finemente ristrutturato è composto da ampia camera matrimoniale, camera doppia, soggiorno/cucina e bagno. Corredato di vano lavanderia con lavatrice. God  …see more

from £68 / night

£424 - £662 / week

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from £68 / night

(1) Very Good 

31

Province of Siena / San Casciano dei Bagni

2 4 1 night min

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

 …see more

from £64 / night

£297 - £831 / week

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from £64 / night

5

Pienza holiday apartment rental

Province of Siena / Pienza

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
“L'angolo di Pienza” for its central position is a good starting point to live an unique experience of life in a rich and delicious small country, with its lively community and its sights.  …see more

from £60 / night

£323 / week

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from £60 / night

19

Province of Siena / San Lorenzo a Merse

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Pet friendly

 …see more

from £62 / night

£382 / week

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from £62 / night

100

Villa rental in Pienza with swimming pool

Province of Siena / Pienza

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in Tuscany Italy, this grand villa is the perfect place for your holidays. The villa features: a swimming Pool, air Conditioning, an internet Connection, a pet friendly space .  …see more

from £417 / night

£2428 - £3323 / week

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from £417 / night

9

Holiday villa in Montepulciano

Province of Siena / Montepulciano

5 13 4 nights min

  • 5 bedrooms
  • Sleeps 13
  • 4 nights min
  • Private garden
La casa gode di panorami tra i pu' belli nella Regione Toscana, la tranquillità e l'ara salubre sono garantiti  …see more

from £170 / night

£170 / week

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from £170 / night

(1) Very Good 

10

Casole d'Elsa / Gallena

28 50 Min stay varies

  • 28 bedrooms
  • Sleeps 50
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

17

Apartment rental in Torri

Sovicille / Torri

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Apartment VIVALDI (max 2 adults) It includes a large double bed, a comfortable lounge with TV and a private bathroom with shower, equipped with Jacuzzi and Steam bath. A traditional kitchen with a fireplace to make you feel the emotions and the atmosphere of the houses  …see more

from £119 / night

£763 / week

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from £119 / night

24

Castelnuovo Berardenga / Casal Monastero

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

Pricing unknown

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Pricing unknown

20

Holiday apartment rental

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Borgo 7 Tigli #5 is a splendid apartment with two bedrooms 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 histor  …see more

from £85 / night

£551 - £755 / week

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from £85 / night

24

Province of Siena / Sinalunga

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min

 …see more

from £43 / night

£297 / week

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from £43 / night

9

Province of Siena / Colle di Val d'Elsa

2 5 Min stay varies

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

 …see more

from £98 / night

£416 - £1450 / week

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from £98 / night

13

Province of Siena / Montepulciano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £102 / night

£712 / week

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from £102 / night

27

Province of Siena / Murlo

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £67 / night

£423 - £933 / week

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from £67 / night

8

Province of Siena / Colle di Val d'Elsa

2 4 Min stay varies

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

 …see more

from £89 / night

£890 / week

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from £89 / night

14

Holiday apartment rental

Province of Siena / Montepulciano

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
Ideal location for a relaxing vacation in the warm atmosphere of an old farmhouse that has retained its original architectural details. The house consists of only one apartment for 8 people. The apartment is on the 1st Stock.  …see more

from £339 / night

£1695 / week

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from £339 / night

19

Apartment rental in Asciano with shared pool

Province of Siena / Asciano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
About 20km far from Siena, at about 2 km from the old centre of Asciano you find the Agritourism. The farmhouse has been recently restored; it is divided into 4 nice, large, and comfortable. apartments. They are ground floor or first floor; each one with an independe  …see more

from £51 / night

£314 - £577 / week

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from £51 / night

6

Province of Siena / Siena

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly

 …see more

from £106 / night

£736 / week

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from £106 / night

12

Province of Siena / Chianciano Terme

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £60 / night

£382 - £500 / week

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from £60 / night

6

Province of Siena / Pienza

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

 …see more

from £60 / night

£255 / week

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from £60 / night

12

Montepulciano holiday b&b rental

Province of Siena / Montepulciano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
A perfect place from which to make day trips or relax in the many seating areas around the garden. Our one-of-a-kind breakfast is served on china with linens and include local hams, cheeses,mouthwatering tarts, crepes or creme caramel.  …see more

from £73 / night

£424 / week

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from £73 / night

100

Guazzino holiday apartment rental

Sinalunga / Guazzino

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Villa Vignacce is a villa in Tuscany divided into three apartments, all recently remodelled, that can be joined to become a single villa with private pool.  …see more

from £98 / night

£678 - £1145 / week

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from £98 / night

11

Asciano / Crete Senesi

2 4 Min stay varies

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

 …see more

from £100 / night

£611 - £763 / week

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from £100 / night

17

Apartment rental in Casole d'Elsa with swimming pool

Province of Siena / Casole d'Elsa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Separate entrance with outdoor lounge furnished and shaded, one double bedroom, bathroom with shower, large living room with sofa bed for two additional seats, a kitchen with a refrigerator.By adding two more people to contact for price.<br />The price is per apar  …see more

from £68 / night

£339 - £551 / week

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from £68 / night

13

Province of Siena / Montepulciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

Pricing unknown

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Pricing unknown

14

Vagliagli holiday apartment rental

Castelnuovo Berardenga / Vagliagli

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
One bedroom apartment of 50sqm located on the first floor with an amazing double stairs entrance, typical of the noble villas of the past. Large living room with fire place, modern kitchen corner, double bedroom and bathroom with shower. Internet Wi fi, Sat Tv, Cd/Dvd  …see more

from £56 / night

£339 - £772 / week

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from £56 / night

13

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

 …see more

from £195 / night

£1365 / week

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from £195 / night

14

Holiday apartment with shared pool in Siena

Province of Siena / Siena

3 7 6 nights min

  • 3 bedrooms
  • Sleeps 7
  • 6 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
Bright and spaciuos apartment for 6-8 people with swimming pool in the charming Castello di San Fabiano in the beautiful Crete Senesi area, 15 minutes from Siena and 30 minutes from Montalcino, Pienza, and Rapolano's thermal baths.  …see more

from £407 / night

£2797 / week

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from £407 / night

22

Holiday apartment with shared pool in Crete Senesi

Asciano / Crete Senesi

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
These rental apartments in Tuscany are part of a little medieval “borgo”, village, recently renovated and converted into a holiday farmhouse.  …see more

from £85 / night

£339 - £755 / week

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from £85 / night

(3) Excellent 

25

Province of Siena / Radda in Chianti

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Pet friendly

 …see more

from £43 / night

£297 / week

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from £43 / night

15

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Ask about pets
San Gimignano, with its location in the Tuscan hills and along the Francigena, offers a unique historical centre. You can have the opportunity to discover the "Vernaccia" wine, Italy's oldest white wine, and much more from nature and gastronomic point of  …see more

from £94 / night

£551 / week

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from £94 / night

36

Province of Siena / Castiglione D'Orcia

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £424 / night

£2967 / week

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from £424 / night

12

Province of Siena / Colle di Val d'Elsa

2 5 3 nights min

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

 …see more

from £77 / night

£509 / week

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from £77 / night