Apartments in Province of Siena and Villas – Holiday Lettings - Holiday Rentals Province of Siena

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Province of Siena

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5,510 Holiday homes

(2) Very Good 

23

Holiday villa with swimming pool in Sinalunga

Province of Siena / Sinalunga

9 31 3 nights min

  • 9 bedrooms
  • Sleeps 31
  • 3 nights min
  • Nearest beach 98 km
  • Swimming pool
  • Child friendly

from £1,062 / night

£7,434 / week

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from £1,062 / night

(1) Excellent 

99

Holiday villa with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

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

from £111 / night

£700 - £1,045 / week

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from £111 / night

(2) Excellent 

16

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Suitable for children age 5+

from £67 / night

£399 / week

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Responds fast!
avg. 41 minutes

from £67 / night

(1) Very Good 

12

Holiday apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly

from £146 / night

£1,208 / week

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from £146 / night

6

Holiday apartment in Pienza

Province of Siena / Pienza

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min

from £62 / night

£266 / week

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from £62 / night

(1) Excellent 

17

Holiday apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 Min stay varies

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

from £53 / night

£359 - £713 / week

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Responds fast!
avg. 1 hour 31 minutes

from £53 / night

(2) Excellent 

18

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 £60 / night

£469 - £735 / week

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from £60 / night

(12) Excellent 

40

Holiday villa with swimming pool in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £220 / night

£1,540 - £2,230 / week

Book View

Responds fast!
avg. 3 hours 9 minutes

from £220 / night

(50) Excellent 

Certificate of Excellence

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
…see more

Certificate of Excellence

from £90 / night

£625 - £900 / week

Book View

from £90 / night

(2) Very Good 

41

Holiday barn with shared pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £100 / night

£700 - £1,230 / week

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from £100 / night

(31) 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
“Perfect cottage for two” Loved everything about our stay here. Alexandra was so helpful, with directions, shopping, restaurants and her love of the wine industry. She met us on the road when we got lost. Lives next door but the property is so big
…see more

from £107 / night

£744 / week

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from £107 / night

(10) Very Good 

12

Holiday apartment in Monteriggioni

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 £80 / night

£558 / week

Book View

from £80 / night

(9) Excellent 

16

Holiday apartment with swimming pool in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

from £80 / night

£425 - £1,000 / week

Book View

Responds fast!
avg. 2 hours 34 minutes

from £80 / night

(1) Excellent 

30

San Gimignano holiday home rental

Province of Siena / San Gimignano

2 4 Min stay varies

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

from £71 / night

£469 - £850 / week

Book View

Responds fast!
avg. 2 hours 47 minutes

from £71 / night

(19) Very Good 

Certificate of Excellence

46

Holiday cottage in Siena

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 65 km
  • Air conditioning

Certificate of Excellence

from £84 / night

£589 / week

Book View

Responds fast!
avg. 2 hours 43 minutes

from £84 / night

(19) Excellent 

19

Apartment rental in San Gimignano

Province of Siena / San Gimignano

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 72 km
  • Child friendly
  • Private garden
“An all round fantastic experience...we have great memories...” My partner and I stayed here for a week in July, and count ourselves lucky to have discovered this place. About 8kms from San Gimignano (an easy jaunt in a car, the latter being vital)
…see more

from £55 / night

£319 - £394 / week

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from £55 / night

6

Holiday home in Vescovado di Murlo

Murlo / Vescovado di Murlo

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Private garden

from £53 / night

£354 - £461 / week

Book View

from £53 / night

(4) Excellent 

19

Torrita di Siena holiday apartment rental

Province of Siena / Torrita di Siena

2 4 2 nights min

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

from £80 / night

£514 / week

Book View

from £80 / night

22

San Rocco a Pilli holiday apartment rental

Sovicille / San Rocco a Pilli

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £62 / night

£354 - £837 / week

Book View

from £62 / night

(6) Excellent 

28

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £80 / night

£558 / week

Book View

from £80 / night

24

Holiday apartment with shared pool in Buonconvento

Province of Siena / Buonconvento

3 14 3 nights min

  • 3 bedrooms
  • Sleeps 14
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £266 / night

£1,328 / week

Book View

from £266 / night

19

San Gimignano holiday farmhouse rental

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £70 / night

£495 - £753 / week

Enquire View

from £70 / night

(1) Excellent 

29

Holiday farmhouse in Montepulciano

Province of Siena / Montepulciano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 116 km
  • Child friendly
  • Pet friendly

from £124 / night

£531 - £620 / week

Book View

from £124 / night

(2) Very Good 

12

Holiday apartment accommodation

Province of Siena / Radicofani

3 6 1 night min

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

from £107 / night

£744 / week

Book View

from £107 / night

(6) Excellent 

26

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £88 / night

£611 - £969 / week

Book View

Responds fast!
avg. 1 hour 41 minutes

from £88 / night

18

Holiday apartment in Siena

Province of Siena / Siena

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 km
  • Child friendly
  • Car not necessary

from £58 / night

£403 / week

Book View

from £58 / night

38

Holiday apartment in Casole d'Elsa

Province of Siena / Casole d'Elsa

1 4 3 nights min

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

from £93 / night

£651 / week

Book View

from £93 / night

(1) Excellent 

23

Farmhouse rental in Chiusdino with shared pool

Province of Siena / Chiusdino

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Nearest beach 38 km
  • Swimming pool
  • Child friendly

from £111 / night

£770 / week

Book View

from £111 / night

(12) Excellent 

19

Holiday apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Pet friendly
“Wonderful, Wonderful, Highly Recommended.” My wife and I stayed 23rd. June - 5th. July 2013, and had a wonderful holiday. So relaxing and no hassle whatsoever. The farmhouse has three one bedroomed apartments available and a fourth which Elena (the
…see more

from £71 / night

£434 - £496 / week

Book View

Responds fast!
avg. 1 hour 44 minutes

from £71 / night

(19) Very Good 

Certificate of Excellence

27

Holiday apartment in Sant Andrea a Montecchio

Siena / Sant Andrea a Montecchio

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Car not necessary
“Reality of a dream!” I was looking for a quiet week with a beautiful panorama not far from Siena, to enjoy after the Palio and before participating in an intensive celebration later in July within Siena. I studied the information on Sant'Andrea a Mon
…see more

Certificate of Excellence

from £53 / night

£310 - £531 / week

Book View

from £53 / night

(11) Excellent 

Certificate of Excellence

52

Apartment rental in Montepulciano

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

Certificate of Excellence

from £124 / night

£753 - £938 / week

Book View

Responds fast!
avg. 3 hours 0 minutes

from £124 / night

(2) Very Good 

10

Apartment rental in Colle di Val d'Elsa with shared pool

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

from £53 / night

£425 / week

Book View

Responds fast!
avg. 1 hour 26 minutes

from £53 / night

11

Holiday apartment with swimming pool in Sinalunga

Province of Siena / Sinalunga

1 2 2 nights min

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

from £89 / night

£602 / week

Book View

from £89 / night

(17) Excellent 

50

Castelnuovo Berardenga holiday apartment rental

Province of Siena / Castelnuovo Berardenga

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“We enjoyed our holidays in this beautiful agriturismo” We have spent two weeks in Fernando Mattii's agriturismo. The site is very clean and very well maintained. Fernando Mattii was always helpful when we needed anything and he even brought us some wo
…see more

from £133 / night

£930 / week

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Responds fast!
avg. 2 hours 57 minutes

from £133 / night

(2) Excellent 

26

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 3 nights min

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

from £107 / night

£620 / week

Book View

from £107 / night

19

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £622 / night

£4,349 / week

Book View

Responds fast!
avg. 2 hours 25 minutes

from £622 / night

(3) Excellent 

22

Villa rental in Siena with swimming pool

Province of Siena / Siena

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly

from £354 / night

£2,036 - £3,540 / week

Book View

from £354 / night

12

Casole d'Elsa holiday apartment rental

Province of Siena / Casole d'Elsa

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £124 / night

£797 / week

Book View

from £124 / night

(2) Very Good 

12

Holiday farmhouse letting

Province of Siena / San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

from £80 / night

£531 / week

Book View

from £80 / night

12

Holiday home with shared pool in Poggibonsi

Province of Siena / Poggibonsi

2 4 Min stay varies

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

from £53 / night

£372 / week

Book View

from £53 / night