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Province of Siena

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1,226 Holiday homes

Filters applied: Private garden

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

(5) Excellent 

21

Holiday villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“An awesome villa in the Tuscan hills” A wonderfully restored church with plenty of character. Privacy with trees and hedges. Fab and accessible pool. Well equipped kitchen. An amazing welcome pack. We cycled from here to San Gimignano and to Monterigg  …see more

from £130 / night

£863 - £1983 / week

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from £130 / night

52

Holiday villa rental

Poggibonsi / Staggia Senese

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £518 / night

£3621 - £4828 / week

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from £518 / night

(4) Excellent 

14

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 55 km
  • Child friendly
  • Ask about pets

from £87 / night

£475 - £733 / week

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from £87 / night

(1) Excellent 

15

Province of Siena / Monteroni d'Arbia

2 4 3 nights min

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

from £57 / night

£363 - £664 / week

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from £57 / night

(11) Excellent 

21

Gracciano holiday cottage rental

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Really worth staying!” My partner and I spent a glorious week this spring at agriturismo Il Salarco surrounded by vineyards and idyllic rolling countryside. The owner, an English lady called Laura, made us both feel really welcome, was fabulously know  …see more

from £69 / night

£380 - £1776 / week

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from £69 / night

12

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

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

from £68 / night

£462 - £669 / week

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from £68 / night

(48) Excellent 

21

Holiday cottage in Montepulciano

Province of Siena / Montepulciano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 158 km
  • Child friendly
  • Air conditioning
“Clean, comfortable and cozy house with privacy and convenience to Montepuciano” We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close  …see more

from £61 / night

£345 - £604 / week

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from £61 / night

(34) Excellent 

24

Apartment rental in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 £52 / night

£337 - £453 / week

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from £52 / night

(18) Excellent 

43

Holiday apartment in Monticchiello

Pienza / Monticchiello

2 6 2 nights min

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

from £65 / night

£319 - £778 / week

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from £65 / night

(9) Excellent 

42

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Air conditioning

from £75 / night

£525 - £785 / week

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from £75 / night

15

Province of Siena / Castellina In Chianti

1 2 3 nights min

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

from £48 / night

£332 / week

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from £48 / night

(12) Excellent 

69

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“A hidden gem.” We stayed at Villa LisiDor at the end of May with family. We made the trip to Tuscany by train to Florence from the UK and hired a car from there. We arrived during an unseasonably chilly spell and in torrential rain after a very l  …see more

from £409 / night

£2858 - £4397 / week

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from £409 / night

22

Holiday villa in Siena

Province of Siena / Siena

5 13 2 nights min

  • 5 bedrooms
  • Sleeps 13
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £2703 / night

£9009 - £11379 / week

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from £2703 / night

(1) Excellent 

27

Holiday barn with swimming pool in Quercegrossa

Monteriggioni / Quercegrossa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £74 / night

£449 - £871 / week

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from £74 / night

13

Province of Siena / Pievescola

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £52 / night

£345 / week

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from £52 / night

(64) Excellent 

52

Holiday villa letting

Province of Siena / Sinalunga

12 26 Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
  • Nearest beach 170 km
  • Swimming pool
  • Child friendly

from £518 / night

£3621 - £7759 / week

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from £518 / night

10

Province of Siena / Siena

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Private garden

from £78 / night

£544 / week

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from £78 / 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

31

San Gimignano / Castel San Gimignano

1 2 3 nights min

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

from £78 / night

£561 / week

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from £78 / night

4

Holiday farmhouse in Radicondoli

Province of Siena / Radicondoli

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 50 km
  • Child friendly
  • Private garden

Pricing unknown

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Pricing unknown

(15) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Very comfortable home away from home” Casacorvo Minore is a very comfortable apartment well located in the heart of Chianti. It has great views from its veranda which fostered perfect starts for each day as we had breakfast sitting in the morning sun.  …see more

from £100 / night

£560 - £760 / week

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from £100 / night

(3) Excellent 

36

Holiday farmhouse in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly

from £95 / night

£561 - £604 / week

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from £95 / night

(4) Excellent 

19

Holiday farmhouse with swimming pool in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Farm estate living in Tuscany is pretty special, truly a unforgettable place to stay with fantastic owners” Great place to stay to truly get away and enjoy the relaxing Tuscany life. The chef at home was fantastic and the local shopping 5-10 minutes a  …see more

from £207 / night

£776 - £2173 / week

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from £207 / night

(1) Excellent 

26

Holiday home in Rigomagno

Sinalunga / Rigomagno

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £81 / night

£561 - £1285 / week

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from £81 / 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  …see more

from £90 / night

£625 - £900 / week

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from £90 / night

(10) Excellent 

26

Province of Siena / Montepulciano

2 4 Min stay varies

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

from £74 / night

£535 - £742 / week

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from £74 / night

(1) Excellent 

45

Province of Siena / Montalcino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £225 / night

£1569 / week

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from £225 / 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

from £155 / night

£1078 - £1682 / week

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from £155 / night

(1) Excellent 

24

Holiday villa with swimming pool in Montalcinello

Chiusdino / Montalcinello

8 18 7 nights min

  • 8 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly

from £339 / night

£2371 - £3880 / week

Enquire View

from £339 / night

(7) Excellent 

35

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £87 / night

£544 - £906 / week

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from £87 / 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

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

(3) Excellent 

28

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 7 nights min

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

from £35 / night

£242 - £828 / week

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from £35 / night

(4) Excellent 

18

Farmhouse rental in Radicofani with shared pool

Province of Siena / Radicofani

2 4 Min stay varies

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

from £104 / night

£518 - £733 / week

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from £104 / night

(3) Excellent 

24

Radicondoli / Belforte

4 9 Min stay varies

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

 …see more

from £186 / night

£1294 - £1897 / week

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from £186 / night

48

Fort letting in Montisi with shared pool

Province of Siena / Montisi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £107 / night

£739 - £821 / week

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from £107 / night

41

Holiday villa rental

Province of Siena / Montepulciano

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly

from £539 / night

£3772 - £5927 / week

Enquire View

from £539 / night

(1) Excellent 

7

Farmhouse rental in Montepulciano with shared pool

Province of Siena / Montepulciano

4 4 Min stay varies

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

from £61 / night

£259 - £449 / week

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from £61 / night

(4) Excellent 

16

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 £78 / night

£414 - £966 / week

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from £78 / 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