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

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Province of Siena

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4,190 Holiday homes

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

(7) Excellent 

7

Province of Siena / Rosia

2 6 2 nights min

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

 …see more

from £76 / night

£416 / week

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from £76 / night

(5) Excellent 

26

Holiday cottage with swimming pool in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
Charming cottage with private pool and pet-friendly near Siena  …see more

from £64 / night

£424 - £1272 / week

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from £64 / night

(2) Excellent 

17

Holiday farmhouse in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 106 km
  • Child friendly
  • Car not necessary
The apartment has two bedrooms one big bathroom and a service bath.The private entrance leads into a spacious lounge furnished with a authentic Tuscan table and chairs, a comfortable sofa set and coffee table and an open plan fire place very spacious and charmin  …see more

from £166 / night

£678 / week

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from £166 / night

(1) Average 

27

Holiday farmhouse letting

Radicondoli / Belforte

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
Situated at the edge of a park, just within 5 minutes walk to the mediaeval hilltop village of Radicondoli, the property enjoys an exceptional view over the Metallifere Hills and those of Chianti, taking in the towers of San Gimignano and stretching as far as the Apenni  …see more

from £51 / night

£339 - £1484 / week

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from £51 / night

24

Holiday farmhouse in Siena

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city  …see more

from £115 / night

£801 / week

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from £115 / night

(7) Very Good 

22

Province of Siena / Montepulciano

2 6 3 nights min

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

 …see more

from £77 / night

£450 / week

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from £77 / 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 £39 / night

£255 / week

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from £39 / night

(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 £77 / night

£509 - £551 / week

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from £77 / night

(3) Very Good 

24

Holiday villa with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly
Located within walking distance of the village of Gaiole in Chianti, the villa offers the perfect setting to explore the Chianti Classico region, enjoy the breathtaking views of the vineyards and olive groves, and experience the charming Tuscan lifestyle.<br />Bea  …see more

from £76 / night

£526 - £1500 / week

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from £76 / night

20

Chiusi holiday manor house rental

Province of Siena / Chiusi

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Beautiful farmhouse divided into separate apartments. Large swimming pool and children's playground.  …see more

from £258 / night

£1806 - £3068 / week

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from £258 / 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 £102 / night

£509 - £721 / week

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from £102 / night

(1) Excellent 

22

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
The Casale is a very nice private villa, reachable through a dirt road easy to go also with a city car! The villa has a private swimming pool, outdoor BBQ and Jacuzzi, 5 bedrooms and 5 bathrooms (at least 10 people), it also has a big kitchen a big living room with fire  …see more

from £280 / night

£1950 / week

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from £280 / night

(6) Very Good 

25

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
Self-catering Tuscany villa with stunning views, just five minutes walk to the village. Private pool and terrace for al fresco dining. Ideal for families and couples seeking relaxation.  …see more

from £61 / night

£424 - £1695 / week

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from £61 / night

(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 £46 / night

£323 - £479 / week

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from £46 / night

5

Province of Siena / Pienza

2 5 1 night min

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

 …see more

from £111 / night

£594 / week

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from £111 / night

18

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £47 / night

£306 - £365 / week

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from £47 / 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

£594 - £1602 / week

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from £89 / 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 £106 / night

£742 / week

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from £106 / night

(4) Excellent 

24

Cottage rental in Casole d'Elsa with swimming pool

Province of Siena / Casole d'Elsa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
“Beautiful location” The villa is lovely & bigger than it looks in the photos! I would recommend it although there are a couple of grumbles! The villa is definately not walking distance to the town. It is down a long, long gravel track, so beautiful  …see more

from £79 / night

£551 - £1187 / week

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from £79 / night

18

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Air conditioning
La naturale estensione del paese di Gaiole in Chianti. Il concetto del “villaggio - nel - villaggio” unico nel suo genere. Il concetto del borgo che diventa parte integrante del villaggio. Una cura maniacale dell' architettura e dei materiali. Disponibi  …see more

from £67 / night

£339 / week

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from £67 / night

16

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

7 13 1 night min

  • 7 bedrooms
  • Sleeps 13
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
We are in a very good position, we are just 3,5 km from San Gimignano, 40 km from Firenze, 25 km from Siena, 25 km from Volterra, 15 km from Certaldo, 45 km from Pisa; you can visit a lots of thinghs and a lots of beautiful historical town.  …see more

from £119 / night

£526 / week

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from £119 / 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
Near to Siena (8 km), in the Chianti region, apartment in farmhouse (size: 170 m2) for max.6 persons. Swimming pool complex and park 3 km far away.Splendid farm house (18 th century) located on the top of a hill. The property apartment offers you the unique and rare  …see more

from £96 / night

£670 - £1034 / week

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from £96 / 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 £132 / night

£856 - £1933 / week

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from £132 / night

11

Province of Siena / Radicofani

1 4 Min stay varies

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

 …see more

from £62 / night

£534 / week

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from £62 / 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 £43 / night

£297 / week

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from £43 / night

(3) Very Good 

23

Holiday farmhouse with shared pool in Buonconvento

Province of Siena / Buonconvento

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A unique and enchanting place” We have been going to Tuscany every summer for a while, and are used to renting houses in beautiful properties… We were not expecting to be surprised and overwelmed again by the beauty of a new place. However, Casanova (  …see more

from £255 / night

£1780 / week

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from £255 / night

(2) Excellent 

19

Holiday apartment in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Child friendly
  • Air conditioning
Staying here will make your holiday unique: wake up in the shadow of the majestic Torre del Mangia is a feeling that isn't easily forgotten.I would like an unforgettable vacation, so I've taken care of all the details of the apartment where I want to welcome g  …see more

from £246 / night

£1611 - £2119 / week

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from £246 / night

46

Holiday castle rental

Province of Siena / Poggibonsi

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Enchanting Winery At the top of a hill with 309 hectares between wood, olive trees and wine yards is located this enchanting winery, with it’s amazing medioeval castle, the pool villa, the farmhouse and a real good Chianti wine production. This property is the ch  …see more

from £509 / night

£3560 - £4865 / week

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from £509 / 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

 …see more

from £60 / night

£416 / week

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from £60 / 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 £120 / night

£839 - £1628 / week

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from £120 / night

14

Holiday villa with swimming pool in Monteroni d'Arbia

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 £315 / night

£2204 - £3178 / week

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from £315 / night

4

Province of Siena / Orgia

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Nearest beach 80 km
  • Private garden

 …see more

from £15 / night

£99 / week

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from £15 / night

(2) Excellent 

17

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful holiday resort near Montepulciano and Pienza  …see more

from £94 / night

£534 - £979 / week

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from £94 / 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 £77 / night

£467 - £492 / week

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from £77 / night

100

Villa rental in Province of Siena with swimming pool

Tuscany / Province of Siena

10 19 7 nights min

  • 10 bedrooms
  • Sleeps 19
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Ideal to accommodate couples and larger groups of people and located amidst a large garden with some splendid views of the surroundings and a very tranquil atmosphere.  …see more

from £339 / night

£2373 - £2967 / week

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from £339 / night

25

Siena holiday villa rental

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies in the hills of southern Tuscany (with a beautiful panorama) around 3 Kms from Radicofani. It forms an ideal starting point for enjoying the peace of the surrounding hills and on the other hand making trips by car (the highway A1 Florence-Rome is 25 Kms f  …see more

from £424 / night

£2034 - £2967 / week

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from £424 / night

(9) Excellent 

5

Province of Siena / Rapolano Terme

4 4 1 night min

  • 4 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £111 / night

£772 / week

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from £111 / night

(4) Excellent 

18

Province of Siena / Radda in Chianti

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £102 / night

£712 / week

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from £102 / night

20

Sarteano holiday manor house rental

Province of Siena / Sarteano

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful stone manor house with heated swimming pool and outdoor heated jacuzzi.  …see more

from £947 / night

£6628 - £15890 / week

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from £947 / 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

£365 - £662 / week

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from £53 / night