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

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Province of Siena

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3,758 Holiday homes

(5) Very Good 

21

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 77 km
  • Swimming pool
  • Child friendly

from £106 / night

£614 - £933 / week

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from £106 / night

34

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £59 / night

£353 - £681 / week

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from £59 / night

(2) Excellent 

24

Castellina In Chianti holiday apartment rental

Province of Siena / Castellina In Chianti

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Private garden

from £97 / night

£736 / week

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from £97 / night

21

Valiano holiday farmhouse rental

Montepulciano / Valiano

5 13 7 nights min

  • 5 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £140 / night

£975 - £2162 / week

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from £140 / night

24

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about pets
  • Private garden

from £181 / night

£1110 - £1942 / week

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from £181 / night

39

Province of Siena / Siena

2 4 2 nights min

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

from £72 / night

£337 / week

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from £72 / night

(4) Excellent 

31

Province of Siena / Murlo

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £68 / night

£407 - £483 / week

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from £68 / night

(8) Excellent 

31

Province of Siena / Siena

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Pet friendly

from £101 / night

£706 / week

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from £101 / night

(46) Excellent 

25

Holiday home with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Perfection in rural Tuscany” From the outset we knew that this place would be special. From reviewing the property on TripAdvisor, looking at the pictures, reading other travellers reviews right through to the wonderful prompt and attentive service r
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from £90 / night

£625 - £900 / week

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from £90 / night

24

Farmhouse rental in Montalcino with swimming pool

Province of Siena / Montalcino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden

from £702 / night

£4908 - £8085 / week

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from £702 / night

(1) Excellent 

12

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 109 km
  • Swimming pool
  • Child friendly

from £93 / night

£631 / week

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from £93 / night

12

Province of Siena / Monteriggioni

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

from £77 / night

£534 / week

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from £77 / night

(3) Excellent 

31

Holiday farmhouse with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Beautiful apartment in glorious country setting in easy reach of Florence, Sienna and other picturesque Tuscan towns” Our host, Grazia, was spot on, really lovely. We were able to communicate in a hilarious mixture of English and Italian. She was fri
…see more

from £64 / night

£442 / week

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from £64 / night

(4) Very Good 

13

Poggibonsi / Staggia Senese

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 74 km
  • Child friendly
  • Pet friendly

from £59 / night

£395 / week

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from £59 / night

(2) Excellent 

12

Province of Siena / Monteriggioni

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Air conditioning

Pricing unknown

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Pricing unknown

20

Holiday farmhouse with shared pool in Larniano

San Gimignano / Larniano

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £111 / night

£619 - £789 / week

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from £111 / night

(4) Excellent 

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 - £1865 / week

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from £255 / night

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

from £47 / night

£328 - £690 / week

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from £47 / 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 £244 / night

£1345 - £1933 / week

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from £244 / night

(4) Excellent 

42

Province of Siena / Siena

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

from £84 / night

£417 / week

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from £84 / night

(11) Excellent 

22

Villa rental in Chiusi

Province of Siena / Chiusi

5 9 1 night min

  • 5 bedrooms
  • Sleeps 9
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“All around fabulous vacation !” We were a group of six and there was plenty of room for everyone. when we arrived, Flaminia our host arranged a lovely welcoming snack and wine, explained everything we needed to know. The location of the villa w
…see more

from £211 / night

£1429 / week

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from £211 / night

10

Province of Siena / Siena

3 6 2 nights min

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

from £84 / night

£582 / week

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from £84 / night

19

Holiday farmhouse with shared pool in Rigomagno

Sinalunga / Rigomagno

2 4 Min stay varies

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

from £143 / night

£832 - £1211 / week

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from £143 / night

10

Macciano holiday farmhouse rental

Chiusi / Macciano

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

from £84 / night

£417 - £592 / week

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from £84 / 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 £73 / night

£505 - £801 / week

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from £73 / night

(2) Excellent 

16

Province of Siena / Sinalunga

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

from £169 / night

£1127 / week

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from £169 / night

(4) Excellent 

23

Holiday apartment in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly

from £101 / night

£673 - £841 / week

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from £101 / night

6

Sovicille / San Rocco a Pilli

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Suitable for children age 5+
  • Pet friendly

from £38 / night

£295 / week

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from £38 / night

(5) Excellent 

14

Holiday home in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Ask about pets

from £80 / night

£547 / week

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from £80 / night

(1) Excellent 

19

San Gimignano holiday farmhouse rental

Province of Siena / San Gimignano

2 4 Min stay varies

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

from £56 / night

£384 - £692 / week

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from £56 / night

27

Province of Siena / Murlo

3 6 Min stay varies

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

from £100 / night

£504 - £925 / week

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from £100 / night

15

Province of Siena / Castellina In Chianti

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 90 km
  • Child friendly
  • Private garden

from £47 / night

£324 / week

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from £47 / night

16

Contignano holiday villa rental

Radicofani / Contignano

9 18 Min stay varies

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

Pricing unknown

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Pricing unknown

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

from £113 / night

£789 - £1174 / week

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from £113 / night

(5) Excellent 

22

Apartment rental in Monteriggioni with swimming pool

Province of Siena / Monteriggioni

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £59 / night

£379 - £467 / week

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from £59 / night

(7) Excellent 

56

Holiday guest house in Siena

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning

from £379 / night

£2311 / week

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from £379 / night

8

Castelnuovo Berardenga / San Gusme

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

from £50 / night

£348 / week

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from £50 / night

23

Holiday apartment with swimming pool in Poggibonsi

Province of Siena / Poggibonsi

3 4 Min stay varies

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

from £131 / night

£765 - £1345 / week

Enquire View

from £131 / night

13

Holiday farmhouse with shared pool in Larniano

San Gimignano / Larniano

1 2 4 nights min

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

from £76 / night

£450 - £619 / week

Enquire View

from £76 / night

(33) Excellent 

32

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Great apartment. Fantastic Tuscan hospitality.” My wife and I chose Casa Gelsomino because we were travelling with our 18-month old daughter and wanted to be in a location with amenities within walking distance. The hamlet of Castel San Gimignano itse
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from £101 / night

£547 - £715 / week

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from £101 / night

1