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

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Province of Siena

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3,989 Holiday homes

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

19

Holiday villa in Pienza

Province of Siena / Pienza

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £158 / night

£1104 - £2069 / week

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from £158 / night

(8) Excellent 

31

Holiday farmhouse with shared pool in Radicondoli

Radicondoli / Belforte

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Authentic Tuscan Getaway!” This was the perfect getaway destination in the middle of the beautiful tuscan countryside. Although set right up in the hills we found the place first time thanks to the directions from the owners who greeted us with a big  …see more

from £104 / night

£725 / week

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from £104 / night

(1) Excellent 

32

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect.” The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arri  …see more

from £281 / night

£1966 - £2535 / week

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from £281 / night

(1) Excellent 

20

Caprera holiday apartment rental

Siena / Caprera

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning

from £69 / night

£432 - £475 / week

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from £69 / night

(2) Very Good 

27

San Gusme holiday villa rental

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Private garden
“wonderful and peaceful place” San Donato is very quiet, a very beautiful place, the garden and all the Villa Arceno aera are amazing, the house is simple but comfortable, and with a soul, as if you ever know this place, I will return one day, for sure  …see more

from £184 / night

£1285 - £1716 / week

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from £184 / night

7

Montepulciano holiday apartment rental

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Private garden

from £61 / night

£259 - £449 / week

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from £61 / night

100

Holiday apartment with shared pool in Chiusdino

Province of Siena / Chiusdino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £87 / night

£561 - £949 / week

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from £87 / 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

from £62 / night

£432 - £1725 / week

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from £62 / night

100

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £272 / night

£1897 - £3621 / week

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from £272 / night

(2) Excellent 

22

Holiday farmhouse with shared pool in Buonconvento

Province of Siena / Buonconvento

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Great place for family and friends” We rented all three cottages for a group of 17 including small children and adults. We couldn't have asked for a better vacation. The area is beautiful, serene and relaxing. Having the pool there took the pressur  …see more

from £143 / night

£1121 / week

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from £143 / night

(32) Excellent 

24

Gaiole in Chianti holiday apartment accommodation

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
“A Little Corner of Heaven” This was our fourth visit to Gaiole in Chianti and our third stay in this apartment. The apartment is modern, well furnished and equipped and spotlessly clean. The garden is beautiful and a real bonus. It is a wonderful  …see more

from £60 / night

£420 - £665 / week

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from £60 / night

5

Province of Siena / Pienza

2 5 1 night min

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

from £113 / night

£604 / week

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from £113 / night

100

Siena holiday apartment rental

Province of Siena / Siena

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly

from £86 / night

£598 - £1020 / week

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from £86 / night

24

Holiday villa rental

Province of Siena / Cetona

10 20 2 nights min

  • 10 bedrooms
  • Sleeps 20
  • 2 nights min
  • Ask owner if suitable for children

from £1054 / night

£3011 - £4192 / week

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from £1054 / 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 £74 / night

£449 - £932 / week

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from £74 / night

34

Holiday villa in Pienza

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £202 / night

£1414 - £2311 / week

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from £202 / night

(11) Excellent 

33

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
“Great stay!” Luca was wonderful to work with. He gave us directions on how to meet him and took us to the apartment to unload the car then helped us find a parking spot. Apartment was very nice, comfortable and close to the city center. Luca was alwa  …see more

from £78 / night

£449 - £545 / week

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from £78 / night

24

Poggibonsi holiday villa rental

Province of Siena / Poggibonsi

1 2 7 nights min

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

from £55 / night

£380 - £613 / week

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from £55 / night

12

Siena holiday apartment rental

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly

from £69 / night

£483 / week

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from £69 / night

(1) Excellent 

29

Province of Siena / Montepulciano

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £250 / night

£1380 - £1983 / week

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from £250 / night

31

Asciano holiday villa let

Province of Siena / Asciano

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £302 / night

£1682 - £3621 / week

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from £302 / night

(2) Very Good 

16

Province of Siena / Chiusi

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly

from £57 / night

£302 / week

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from £57 / 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

from £143 / night

£1001 - £2220 / week

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from £143 / 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

from £124 / night

£863 - £1483 / week

Enquire View

from £124 / night

20

Holiday farmhouse rental

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Nearest beach 44 km
  • Swimming pool
  • Child friendly

from £355 / night

£2483 - £6397 / week

Enquire View

from £355 / night

24

San Casciano dei Bagni / Celle sul Rigo

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning
  • Pet friendly

from £69 / night

£302 / week

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from £69 / night

100

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly

from £259 / night

£1811 - £3104 / week

Enquire View

from £259 / night

(6) Excellent 

36

Holiday guest house in Siena

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden

from £48 / night

£432 - £649 / week

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from £48 / night

(2) Excellent 

43

Siena / Val di Merse

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £108 / night

£768 - £1595 / week

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from £108 / 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 £130 / night

£1018 - £2242 / week

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from £130 / night

25

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning

from £89 / night

£694 / week

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from £89 / night

(3) Excellent 

36

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

from £192 / night

£1272 - £4232 / week

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from £192 / night

(1) Excellent 

23

Holiday villa with shared pool in Montepulciano

Province of Siena / Montepulciano

4 2 Min stay varies

  • 4 bedrooms
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Ask owner if suitable for children
“Old-world Italian charm in a beautiful Tuscan setting” It's a job to find it it, but once you do, you'll want to stay longer than you've booked for. The house has been in the family since 1812 - they produce their own wine - and Olimpia is a charming  …see more

from £44 / night

£302 / week

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from £44 / night

24

Province of Siena / Palazzone

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

Pricing unknown

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Pricing unknown

(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

from £173 / night

£1207 - £1811 / week

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from £173 / night

(1) Excellent 

9

Province of Siena / Pienza

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 98 km
  • Swimming pool
  • Child friendly

from £182 / night

£613 - £992 / week

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from £182 / night

(1) Excellent 

25

Murlo / Casciano di Murlo

5 11 3 nights min

  • 5 bedrooms
  • Sleeps 11
  • 3 nights min
  • Nearest beach 70 km
  • Child friendly
  • Private garden

from £76 / night

£535 - £699 / week

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from £76 / night

(1) Excellent 

33

Chiusi holiday b&b accommodation

Province of Siena / Chiusi

1 4 1 night min

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

from £57 / night

£302 / week

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from £57 / night

(13) Excellent 

41

Asciano / Crete Senesi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £61 / night

£423 - £733 / week

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from £61 / 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

from £69 / night

£345 / week

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from £69 / night

1