Province of Siena apartment or villa with a private pool area | Holiday Lettings

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Province of Siena

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926 Holiday homes

Filters applied: Private pool

(9) Excellent 

57

Holiday lodge in Pienza

Province of Siena / Pienza

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £220 / night

£1539 - £2807 / week

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from £220 / 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 £61 / night

£388 - £479 / week

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from £61 / 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 £720 / night

£5035 - £8294 / week

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from £720 / night

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

60

Holiday villa with swimming pool in Bettolle

Sinalunga / Bettolle

11 22 7 nights min

  • 11 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £786 / night

£5496 - £7005 / week

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from £786 / night

(6) Excellent 

32

Holiday home with swimming pool in Radicondoli

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Fabulous house in glorious location” Lovely welcome from Elsa - an fantastic traditional meal mid week. The house was beautiful and spacious with everything you could need. Children - 8, 10, 12, 13 loved house and garden - especially the tortoise!
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from £99 / night

£690 - £1078 / week

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from £99 / night

(10) Excellent 

10

Holiday townhouse with swimming pool in Sovicille

Province of Siena / Sovicille

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

from £39 / night

£544 - £2263 / week

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from £39 / night

(1) Excellent 

45

Montalcino holiday farmhouse accommodation

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

(15) Excellent 

34

Holiday apartment in Poggibonsi

Province of Siena / Poggibonsi

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
“Trust the reviews .... You won't be disappointed” We were a family group of 5 with children ages of 12, 16 and 18. The hosts Francesco and Eleanor make you feel at home from the minute you arrive to the time you sadly have to leave. They are around if
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from £113 / night

£785 - £1630 / week

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from £113 / night

(4) 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

(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,
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from £104 / night

£725 / week

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from £104 / night

(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

20

Montepulciano holiday farmhouse rental

Province of Siena / Montepulciano

3 6 Min stay varies

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

from £147 / night

£863 - £1768 / week

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from £147 / night

(1) Very Good 

35

Villa accommodation in San Gimignano with swimming pool

Province of Siena / San Gimignano

7 10 Min stay varies

  • 7 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £186 / night

£1294 - £2069 / week

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from £186 / night

24

Palazzone holiday farmhouse rental

Province of Siena / Palazzone

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly

Pricing unknown

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Pricing unknown

9

Colle di Val d'Elsa holiday farmhouse rental

Province of Siena / Colle di Val d'Elsa

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £100 / night

£682 - £1475 / week

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from £100 / night

100

Gaiole in Chianti holiday villa rental

Province of Siena / Gaiole in Chianti

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

from £397 / night

£2759 - £3880 / week

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from £397 / night

(6) Very Good 

24

Cottage rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Peace and tranquility” My wife and I stayed here in June 2012. On arrival we were stuned by how beautiful the house, the grounds and the surrounding valleys were. The gardens are well maintained as with the house. There are numerous sitting areas outs
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from £74 / night

£518 - £1509 / week

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from £74 / night

(11) Excellent 

39

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £173 / night

£1207 - £1682 / week

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from £173 / night

(1) Excellent 

22

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £285 / night

£1983 / week

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from £285 / night

31

Montepulciano holiday villa let

Province of Siena / Montepulciano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Private garden

from £163 / night

£1138 - £2104 / week

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from £163 / night

16

Holiday villa rental

Province of Siena / Cetona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Pet friendly
  • Private garden

from £270 / night

£1890 - £3780 / week

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from £270 / night

(7) Excellent 

24

Val d'Orcia holiday villa rental

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £271 / night

£1897 - £2074 / week

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from £271 / night

(13) Excellent 

40

Holiday apartment with swimming pool in Crete Senesi

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 - £707 / week

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from £61 / night

24

Celle sul Rigo holiday villa rental

San Casciano dei Bagni / Celle sul Rigo

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £198 / night

£1380 - £2352 / week

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from £198 / night

(17) Excellent 

26

Casole d'Elsa holiday cottage rental

Province of Siena / Casole d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Everything we wanted: excellent villa with lovely pool, beautiful countryside views and welcoming owners.” La Casa Dei Nonni was above and beyond our expectations. The location within the Tuscan hillside village of Monteguidi was easy to find from the
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from £130 / night

£776 - £1164 / week

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from £130 / night

(4) Excellent 

17

Holiday villa rental

Province of Siena / Gaiole in Chianti

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
“Authentic unspoiled Italian charm!” My family and I stayed at this beautiful property and had a relaxed and wonderful holiday. Gaiole in Chianti is a small village totally unspoilt by tourism and the location of this property is ideal if you hire a ca
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from £104 / night

£518 / week

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from £104 / night

(4) Excellent 

20

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £138 / night

£587 - £923 / week

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from £138 / night

(6) Very Good 

43

Gaiole in Chianti holiday home accommodation

Gaiole in Chianti / Montefienali

3 6 Min stay varies

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

from £47 / night

£269 - £604 / week

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from £47 / night

20

Holiday manor house rental

Province of Siena / Chiusi

8 21 7 nights min

  • 8 bedrooms
  • Sleeps 21
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool

from £307 / night

£2147 - £3216 / week

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from £307 / night

22

Holiday apartment with swimming pool in Crete Senesi

Asciano / Crete Senesi

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £104 / night

£725 / week

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from £104 / night

32

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £130 / night

£906 - £1630 / week

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from £130 / night

15

Siena holiday farmhouse rental

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

from £74 / night

£345 - £819 / week

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from £74 / night

(3) Excellent 

24

Holiday b&b with swimming pool in Palazzone

Province of Siena / Palazzone

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Private garden

Pricing unknown

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Pricing unknown

(7) Very Good 

34

Radicondoli holiday villa rental

Province of Siena / Radicondoli

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly

from £302 / night

£1026 - £2371 / week

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from £302 / night

(21) Excellent 

20

Holiday farmhouse with swimming pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
“Fabulous Tuscan villa experience!” Casa Bassa is a beautiful old Tuscan farmhouse and was the perfect central point for our stay in Tuscany. We were a party of 7, ranging in age from 16 to 63, and found the villa gave us ample space to gather togethe
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from £250 / night

£2000 - £2750 / week

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from £250 / night

24

Holiday farmhouse with swimming pool in Pienza

Province of Siena / Pienza

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £354 / night

£2469 - £3381 / week

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from £354 / night

14

Holiday villa with swimming pool in Montaperti

Castelnuovo Berardenga / Montaperti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £190 / night

£845 - £1897 / week

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from £190 / night

15

Holiday cottage rental

Province of Siena / Radicofani

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £69 / night

£388 / week

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from £69 / night

(13) Excellent 

43

Holiday villa in Staggia

Poggibonsi / Staggia

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“Best vacation ever!” Our entire experience at Villa Vianci was beyond expectations. We travelled with 4 generations, ages 3 1/2 to 85! The villa was spectacular, spacious & immaculate. The pictures on line don't do it justice. Tommasso & Chiara we
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from £302 / night

£3621 / week

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from £302 / night

1