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

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Province of Siena

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723 Holiday homes

Filters applied: Private pool

(10) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £40 / night

£553 - £2303 / week

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from £40 / 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 £799 / night

£5593 - £7128 / week

Enquire View

from £799 / night

100

Cetona holiday villa rental

Province of Siena / Cetona

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly

from £395 / night

£2632 - £4913 / week

Enquire View

from £395 / night

23

Holiday villa with swimming pool in Monticiano

Province of Siena / Monticiano

9 9 Min stay varies

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

Pricing unknown

Enquire View

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 £101 / night

£693 - £1500 / week

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from £101 / night

29

Holiday villa with swimming pool in Radicondoli

Province of Siena / Radicondoli

5 10 7 nights min

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

from £439 / night

£3071 / week

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from £439 / night

(1) Excellent 

46

Holiday castle rental

Province of Siena / Poggibonsi

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £527 / night

£3685 - £5036 / week

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from £527 / night

(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
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from £132 / night

£878 - £2018 / week

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Responds fast!
avg. 49 minutes

from £132 / night

100

Holiday villa with swimming pool in Monticiano

Province of Siena / Monticiano

9 18 2 nights min

  • 9 bedrooms
  • Sleeps 18
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £965 / night

£6579 / week

Enquire View

from £965 / night

(6) Very Good 

39

Holiday villa rental

Province of Siena / Chianciano Terme

4 10 Min stay varies

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

from £176 / night

£1316 - £2369 / week

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Responds fast!
avg. 3 hours 47 minutes

from £176 / night

100

Gaiole in Chianti holiday villa rental

Province of Siena / Gaiole in Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

from £404 / night

£2808 - £4123 / week

Enquire View

from £404 / 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 £106 / night

£737 / week

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from £106 / 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 £106 / night

£737 / week

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from £106 / night

25

Holiday villa with swimming pool in Sinalunga

Province of Siena / Sinalunga

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £251 / night

£1755 - £3422 / week

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from £251 / night

(1) Excellent 

54

Cetona holiday farmhouse rental

Province of Siena / Cetona

8 12 Min stay varies

  • 8 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 29 km
  • Swimming pool

from £308 / night

£2106 - £4685 / week

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from £308 / night

(6) Very Good 

Certificate of Excellence

43

Montefienali 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

Certificate of Excellence

from £48 / night

£274 - £615 / week

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Responds fast!
avg. 1 hour 43 minutes

from £48 / night

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 £303 / night

£2115 - £2983 / week

Enquire View

from £303 / 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
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from £66 / night

£461 / week

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Responds fast!
avg. 1 hour 41 minutes

from £66 / night

4

Chiusi holiday b&b rental

Province of Siena / Chiusi

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

Pricing unknown

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Pricing unknown

18

Pienza holiday villa rental

Province of Siena / Pienza

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly

from £527 / night

£2808 - £4036 / week

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from £527 / 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 £313 / night

£2185 - £3272 / week

Enquire View

from £313 / 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 £360 / night

£2513 - £3440 / week

Enquire View

from £360 / night

(4) 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 £79 / night

£422 - £834 / week

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Responds fast!
avg. 2 hours 19 minutes

from £79 / 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
…see more

from £250 / night

£2000 - £2750 / week

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from £250 / night

37

Sinalunga holiday villa rental

Province of Siena / Sinalunga

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Pet friendly
  • Private garden

from £229 / night

£1579 - £2062 / week

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from £229 / night

18

Siena holiday villa rental

Province of Siena / Siena

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £865 / night

£3509 - £6053 / week

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from £865 / night

18

Villa rental in Gaiole in Chianti with swimming pool

Province of Siena / Gaiole in Chianti

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

from £170 / night

£1404 - £2461 / week

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Responds fast!
avg. 2 hours 52 minutes

from £170 / night

31

Asciano holiday villa let

Province of Siena / Asciano

5 9 5 nights min

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

from £308 / night

£1711 - £3685 / week

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Responds fast!
avg. 2 hours 45 minutes

from £308 / night

18

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £399 / night

£2790 - £3939 / week

Enquire View

from £399 / night

27

Radicondoli holiday home rental

Province of Siena / Radicondoli

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £84 / night

£571 - £1316 / week

Enquire View

from £84 / night

22

Holiday villa rental

Colle di Val d'Elsa / Campiglia dei Foci

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £141 / night

£1404 - £2632 / week

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from £141 / night

35

Holiday villa rental

Province of Siena / Ville di Corsano

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly

from £596 / night

£4167 - £6360 / week

Enquire View

from £596 / night

(6) Excellent 

46

Holiday farmhouse rental

San Gimignano / Montauto

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £214 / night

£1492 / week

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Responds fast!
avg. 1 hour 27 minutes

from £214 / night

(7) Excellent 

128

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £658 / night

£2799 - £4358 / week

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from £658 / night

(43) Excellent 

39

Holiday villa in Siena

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Perfect villa in perfect location” I need to start to say thank you to Jacopo and Fabio that made our holiday and stay absolutely perfect. They were both so helpful and such a pleasure to liaise with, even if we arrived later than expected! The
…see more

from £281 / night

£1711 - £4650 / week

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from £281 / 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 £150 / night

£878 - £1799 / week

Enquire View

from £150 / night

11

Holiday villa in Montefollonico

Torrita di Siena / Montefollonico

3 6 1 night min

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

from £53 / night

£369 / week

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Responds fast!
avg. 3 hours 20 minutes

from £53 / night

23

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £538 / night

£3764 - £5150 / week

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from £538 / night

(6) Very Good 

25

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £63 / night

£439 - £1755 / week

Enquire View

from £63 / 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 £290 / night

£2018 / week

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from £290 / night