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

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Province of Siena

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4,340 Holiday homes

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

40

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
The watermill “Il Molinaccio”, near the renaissance town of Montepulciano, was already present in the old maps of the Granduchy of Tuscany . The original building, duly and let me say passionately restored, now reopens as a luxury country house where the gue  …see more

from £96 / night

£522 / week

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from £96 / night

(1) Very Good 

16

Province of Siena / Siena

1 4 2 nights min

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

 …see more

from £61 / night

£305 / week

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from £61 / night

(1) Excellent 

16

Apartment rental in Casole d'Elsa with shared pool

Province of Siena / Casole d'Elsa

1 7 3 nights min

  • 1 bedroom
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Apt with terrace and large shared pool in an ancient borgo nestled in the countryside between Siena, San Gimignano and Volterra. It hosts 4 people comfortably, has 7 beds. Large living room with kitchen corner and a loft, master bedroom and bathroom with shower. It ha  …see more

from £60 / night

£366 - £518 / week

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from £60 / night

Featured properties

(3) Very Good 

24

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 £261 / night

£1827 / week

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from £261 / night

(3) Very Good 

24

Casole d'Elsa holiday cottage rental

Province of Siena / Casole d'Elsa

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Typical Tuscan barn transformed into a cozy holiday home with private pool located on a panoramic hill with commanding views over the rolling Tuscan hills and the close small hilltop town of Casole d' Elsa. Laying at the edge of a small olive grove and in a superb  …see more

from £66 / night

£439 - £1229 / week

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from £66 / night

(8) Excellent 

24

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • 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 £140 / night

£957 / week

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from £140 / night

(1) Excellent 

18

Province of Siena / Montepulciano

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £57 / night

£374 - £679 / week

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from £57 / night

25

Holiday apartment with shared pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This 65sqm apartment is on one floor only and consists of a sitting room with dining area, fireplace and double divan bed, a small fully equipped kitchen, a double bedroom with a bathroom fitted with shower, a twin bedroom and a bathroom with both bathtub and shower.  …see more

from £122 / night

£766 - £1418 / week

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from £122 / night

(7) Excellent 

24

Val d'Orcia holiday villa rental

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
One of three unique and charming apartments in a XVI century villa situated in the wonderful senese countryside a few km's from Montalcino, in the natural park of the Val d' Orcia, a precious architectural and natural context.Here you will feel embraced by  …see more

from £237 / night

£1653 - £2092 / week

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from £237 / night

(2) Excellent 

24

Farmhouse letting in Radda in Chianti

Province of Siena / Radda in Chianti

2 3 5 nights min

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min
  • 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 work  …see more

from £66 / night

£395 / week

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from £66 / night

(3) Very Good 

21

Sovicille / Torri

1 3 Min stay varies

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

 …see more

from £79 / night

£479 / week

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from £79 / night

(3) Very Good 

26

Holiday apartment rental

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Just as expected!” From our first enquiry, the owners were always so helpful and our stay at the Muricce was everything we wanted it to be. This is a wonderful place to stay, and to tour from. There is something to see or to visit in all directions.  …see more

from £84 / night

£457 - £948 / week

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from £84 / night

55

Holiday villa in Quercegrossa

Monteriggioni / Quercegrossa

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Basciano. The house 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.  …see more

from £258 / night

£1800 - £4453 / week

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from £258 / night

(1) Average 

10

Colle di Val d'Elsa / Campiglia dei Foci

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 68 km
  • Swimming pool
  • Child friendly

 …see more

from £62 / night

£334 - £693 / week

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from £62 / night

44

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £117 / night

£816 - £1215 / week

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from £117 / 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 £71 / night

£457 - £865 / week

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from £71 / night

(1) Average 

28

San Gimignano / Castel San Gimignano

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

 …see more

from £79 / night

£571 / week

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from £79 / night

18

Holiday apartment in Sant'Albino

Montepulciano / Sant'Albino

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Macine (60 m2) for 4 people : Lovely downfloor apartment composed of Sitting/dining room with kitchen all furnished , double bedroom, twin bedroom, bathroom with bath. .A small swimming pool (5x10 m) has been installed in the garden , all over the trees. Around t  …see more

from £66 / night

£461 / week

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from £66 / night

(2) Excellent 

63

Villa rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town. A small church with an enchanting bell tower is preserved in its original for  …see more

from £522 / night

£3392 - £3740 / week

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from £522 / night

(14) Excellent 

24

Holiday villa in San Gimignano

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“If only we could live here!” We spent the 1st 2 weeks of June here with 7 of us in total, 6 adults 1 child. The property is fantastic, it has all the facilities you want with huge rooms. We didn't realise that 2 of the rooms were adjoining which was a  …see more

from £174 / night

£1566 - £2783 / week

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from £174 / night

47

Fort rental in Montisi with shared pool

Province of Siena / Montisi

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Romantic and charming 14th century fortress. Very authentic medieval atmosphere. Strategically located between Val d'Orcia and Crete Senesi, close to Montalcino, Montepulciano, Pienza and Siena. Shops at walking distance. Organic wine and extra virgin olive oil.  …see more

from £158 / night

£1077 - £1176 / week

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from £158 / night

(34) Excellent 

24

Apartment rental in Val di Merse

Siena / Val di Merse

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly
“What you imagine when you think "Tuscany"!” We stayed in La Verbena, and it was amazing. Podere Sortoiano is about 15 minutes out of Siena, but it is so worth it to stay out of the city! It's incredibly quiet and relaxing, and the stars are unlike any  …see more

from £48 / night

£340 - £431 / week

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from £48 / 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 £44 / night

£305 / week

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from £44 / night

17

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Small farmhouse with swimming pool which can be covered.  …see more

from £125 / night

£870 - £1496 / week

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from £125 / night

(21) Excellent 

60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

 …see more

from £48 / night

£292 - £422 / week

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from £48 / 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 £122 / night

£482 - £728 / week

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from £122 / night

29

Holiday apartment with shared pool in Torrita di Siena

Province of Siena / Torrita di Siena

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £53 / night

£366 - £696 / week

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from £53 / night

60

Holiday villa with swimming pool in Bettolle

Sinalunga / Bettolle

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Originally a country estate dating back to 1795, this superb Leopoldine villa blends outstanding elegance and comfort with traditional rustic features which reflect its long history. It retains the typical rooftop pigeon-loft, now romantically transformed into an extra-  …see more

from £1067 / night

£5979 - £7066 / week

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from £1067 / 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 £170 / night

£696 / week

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from £170 / night

(1) Excellent 

12

Province of Siena / Radicofani

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £105 / night

£731 / week

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from £105 / night

(4) Excellent 

19

Province of Siena / San Gimignano

2 4 Min stay varies

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

 …see more

from £62 / night

£369 - £492 / week

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from £62 / 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 £156 / night

£1087 - £1696 / week

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from £156 / night

(2) Very Good 

18

Holiday apartment in Sarteano

Province of Siena / Sarteano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 120 km
  • Child friendly
“good location & helpful landlord” Sarteano is a great location for seeing the rest of Tuscany and for experiencing "la dolce vita" in a small town. The people of Sarteano are very nice and helpful. The owner, Leonardo was especially helpful wit the a  …see more

from £53 / night

£253 / week

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from £53 / night

4

Holiday apartment in San Fabiano

Monteroni d'Arbia / San Fabiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The villa Podernovo offers a nice apartment called Il Forno, with stunning view on the sunflowers fields, with all comforts such air conditioning and heated swimming pool. The apartment Il Forno is at first floor of the villa, with a master bedroom with king size bed,  …see more

from £114 / night

£653 - £870 / week

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from £114 / night

33

Murlo / Casciano di Murlo

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning

 …see more

from £53 / night

£314 / week

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from £53 / night

(3) Very Good 

20

Province of Siena / Siena

1 2 1 night min

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

 …see more

from £87 / night

£566 - £687 / week

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from £87 / night

7

Province of Siena / Montepulciano

2 4 1 night min

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

 …see more

from £66 / night

£386 / week

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from £66 / night

(3) Excellent 

24

Poggibonsi / Staggia Senese

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from £28 / night

£174 - £209 / week

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from £28 / 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 £261 / night

£1827 - £3131 / week

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from £261 / night

100

Holiday apartment rental

Province of Siena / Asciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
These accommodations offer a swimming pool, a living room with dining area, fully equipped kitchen and one or two bathrooms with shower or bathtub. Guests are accommodated in double, twin or single bedrooms.  …see more

from £114 / night

£566 - £887 / week

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from £114 / night