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

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Province of Siena

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3,967 Holiday homes

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

(4) Very Good 

24

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £61 / night

£423 / week

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from £61 / night

25

Pienza holiday lodge rental

Province of Siena / Pienza

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Air conditioning

from £74 / night

£513 - £815 / week

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from £74 / night

22

Villa rental in San Giovanni d'Asso with swimming pool

Province of Siena / San Giovanni d'Asso

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £686 / night

£4800 - £5850 / week

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from £686 / night

100

Villa rental in San Gimignano with swimming pool

Province of Siena / San Gimignano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £456 / night

£3190 - £4138 / week

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from £456 / night

9

Rapolano Terme / Serre di Rapolano

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly

from £61 / night

£388 / week

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from £61 / night

(1) Excellent 

21

Province of Siena / Sarteano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £259 / night

£1380 - £1725 / week

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from £259 / night

100

Holiday apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly

from £96 / night

£670 - £1256 / week

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from £96 / night

100

Holiday villa with swimming pool, tennis court in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly

from £1232 / night

£8618 / week

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from £1232 / 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 £345 / night

£1552 - £2759 / week

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from £345 / night

100

Holiday villa in Montepulciano

Province of Siena / Montepulciano

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 140 km
  • Child friendly

from £161 / night

£1121 - £1811 / week

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from £161 / night

(5) Excellent 

20

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

Pricing unknown

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Pricing unknown

15

Holiday farmhouse with swimming pool in Cetona

Province of Siena / Cetona

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £297 / night

£2078 - £2932 / week

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from £297 / night

(7) Very Good 

45

Holiday villa with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
“Our Dream Villa in Tuscany” We traveled to Tuscany because it was my daughter's dream vacation to celebrate her 50th birthday. Her family of 2 boys and husband, myself and we were later joined by her brother and spouse. We spent two weeks at La Casa i  …see more

from £173 / night

£949 - £2225 / week

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from £173 / 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

(9) Very Good 

6

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Pet friendly

from £44 / night

£302 / week

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from £44 / night

23

Holiday villa in Volpaia

Radda in Chianti / Volpaia

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden

from £311 / night

£2173 - £3432 / week

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from £311 / 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

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from £259 / night

20

Chiusi holiday villa rental

Province of Siena / Chiusi

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £146 / night

£1018 - £2578 / week

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from £146 / night

5

Province of Siena / Rapolano Terme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £78 / night

£544 - £604 / week

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from £78 / night

6

Province of Siena / Montepulciano

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Private garden

from £147 / night

£863 / week

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from £147 / night

(22) 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

£289 - £419 / week

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from £48 / night

(30) Excellent 

26

Holiday farmhouse with swimming pool in Val d'Orcia

Montalcino / Val d'Orcia

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
“Great Location” We can only reiterate the excellent reviews that have gone before. Fonte Aulente is in a great location, quiet and secluded with amazing views of the Tuscan countryside and close to the beautiful town of Montalcino. The accommodation,  …see more

from £104 / night

£725 / week

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from £104 / night

100

Holiday villa with swimming pool, tennis court in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £1632 / night

£11418 - £16492 / week

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from £1632 / night

21

Villa rental in Pienza

Province of Siena / Pienza

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 95 km
  • Child friendly
  • Private garden

from £87 / night

£608 - £884 / week

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from £87 / 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

from £48 / night

£311 - £371 / week

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from £48 / night

20

Holiday home in Asciano

Province of Siena / Asciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

from £89 / night

£621 - £1009 / week

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from £89 / night

30

San Gusme holiday villa rental

Castelnuovo Berardenga / San Gusme

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly

from £144 / night

£1003 - £1401 / week

Enquire View

from £144 / night

55

Province of Siena / Cetona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from £104 / night

£604 - £733 / week

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from £104 / night

19

Crete Senesi holiday apartment rental

Asciano / Crete Senesi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £95 / night

£357 - £690 / week

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from £95 / night

(1) Excellent 

18

Sinalunga holiday apartment rental

Province of Siena / Sinalunga

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly

from £88 / night

£613 - £1078 / week

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from £88 / night

(6) Very Good 

24

Farmhouse rental in Caprera

Siena / Caprera

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning

from £164 / night

£1078 / week

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from £164 / 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

Enquire View

from £55 / night

19

Holiday villa with swimming pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £499 / night

£1996 / week

Enquire View

from £499 / night

(7) Very Good 

22

Province of Siena / Montepulciano

2 6 3 nights min

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

from £78 / night

£457 / week

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from £78 / night

(9) Excellent 

16

Holiday farmhouse in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £63 / night

£432 - £785 / week

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from £63 / night

(6) Excellent 

23

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
“Absolutely wonderful and picturesque!” We rented this beautiful house with two other couples for two weeks and absolutely loved our stay. Barbara and her family are gracious and kind hosts, always going our of their way to make our stay comfortable a  …see more

from £302 / night

£1337 - £2156 / week

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from £302 / night

(6) Very Good 

24

Holiday apartment rental

Siena / Val di Merse

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly

from £173 / night

£949 - £1207 / week

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from £173 / night

100

Holiday apartment in Guazzino

Sinalunga / Guazzino

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 90 km
  • Child friendly

from £48 / night

£302 - £483 / week

Enquire View

from £48 / night

(6) Very Good 

56

Torrita di Siena / Montefollonico

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £164 / night

£1147 / week

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from £164 / night

(3) Excellent 

22

Holiday villa rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £255 / night

£1078 - £2285 / week

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from £255 / night

1