Villas with a pool Province of Siena | Apartments to rent with swimming facilities | Holiday Lettings

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Province of Siena

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2,260 Holiday homes

Filters applied: Swimming pool

(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
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from £319 / night

£2229 - £4286 / week

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from £319 / night

(6) Excellent 

36

Holiday villa with indoor pool in Radicondoli

Province of Siena / Radicondoli

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 79 km
  • Swimming pool
  • Child friendly

from £253 / night

£1765 / week

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Responds fast!
avg. 28 minutes

from £253 / night

17

Holiday farmhouse in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

1 4 Min stay varies

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

from £94 / night

£411 - £644 / week

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Responds fast!
avg. 42 minutes

from £94 / 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
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from £68 / night

£370 - £1732 / week

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Responds fast!
avg. 2 hours 13 minutes

from £68 / night

(2) Excellent 

21

Holiday apartment with shared pool, golf nearby in Buonconvento

Province of Siena / Buonconvento

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £72 / night

£505 - £925 / week

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Responds fast!
avg. 3 hours 39 minutes

from £72 / night

(1) Excellent 

20

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

from £47 / night

£328 - £619 / week

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from £47 / night

(3) Excellent 

28

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 7 7 nights min

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

from £35 / night

£244 - £832 / week

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Responds fast!
avg. 1 hour 26 minutes

from £35 / 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 £85 / night

£530 - £883 / week

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from £85 / night

19

Holiday farmhouse in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

1 4 Min stay varies

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

from £94 / night

£411 - £644 / week

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Responds fast!
avg. 42 minutes

from £94 / night

(8) Excellent 

24

Rapolano Terme / Serre di Rapolano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £80 / night

£547 / week

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from £80 / night

(7) Very Good 

27

Radicondoli holiday cottage rental

Province of Siena / Radicondoli

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £51 / night

£337 - £1471 / week

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from £51 / night

(2) Very Good 

20

Apartment rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

2 4 Min stay varies

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

from £65 / night

£379 - £631 / week

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Responds fast!
avg. 42 minutes

from £65 / night

12

Holiday farmhouse in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

1 4 Min stay varies

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

from £95 / night

£441 - £687 / week

Enquire View

Responds fast!
avg. 42 minutes

from £95 / night

18

Holiday farmhouse accommodation

Province of Siena / San Casciano dei Bagni

3 6 Min stay varies

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

from £178 / night

£619 - £1026 / week

Enquire View

Responds fast!
avg. 42 minutes

from £178 / night

(7) 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 £169 / night

£900 - £2269 / week

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from £169 / night

(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.
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from £100 / night

£560 - £760 / week

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from £100 / night

(1) Excellent 

24

Villa rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £384 / night

£2299 - £3969 / week

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Responds fast!
avg. 3 hours 28 minutes

from £384 / 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 £80 / night

£547 - £1261 / week

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from £80 / night

(13) Excellent 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect and plaisant location to explore Tuscany” We were 4 people staying in this very nice apartment : comfortable, clean, modern, well equipped. We loved the location. I never heard of Gaiole before, but it was a nice discovery. Quiet village, but
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from £175 / night

£1100 - £1600 / week

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from £175 / night

(3) Very Good 

24

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
“Well-located and roomy house” We were 10 adults and two children (three generations) spending one week at the house in May of 2014. We found the house very suitable (for five couples) since it had five large bedrooms. It was very convenient that each
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from £229 / night

£1597 - £2858 / week

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from £229 / night

20

Holiday farmhouse with swimming pool in Ponte d'Arbia

Monteroni d'Arbia / Ponte d'Arbia

7 13 7 nights min

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

from £303 / night

£2119 - £3899 / week

Enquire View

Responds fast!
avg. 42 minutes

from £303 / night

21

Holiday farmhouse rental

Province of Siena / San Casciano dei Bagni

2 7 7 nights min

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

from £94 / night

£655 - £925 / week

Enquire View

Responds fast!
avg. 42 minutes

from £94 / night

(11) 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
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from £77 / night

£475 - £534 / week

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Responds fast!
avg. 1 hour 20 minutes

from £77 / night

(1) Very Good 

18

B&b letting in Montepulciano with shared pool

Province of Siena / Montepulciano

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“nice place, nice people” Living for a bit in an old fashioned atmosphere. It is a confortable and friendly place to stay with your family , friends or alone both relaxing in a wonderful Tuscany landscape and travelling around to explore Reinassance
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from £30 / night

£208 / week

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Responds fast!
avg. 1 hour 50 minutes

from £30 / night

22

Castellina In Chianti holiday farmhouse rental

Province of Siena / Castellina In Chianti

2 4 Min stay varies

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

from £112 / night

£659 - £1105 / week

Enquire View

Responds fast!
avg. 42 minutes

from £112 / night

(11) Very Good 

32

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Excellent value Tuscan villa in a lovely setting” We stayed in the Agrifolo apartment at Le Fontanelle in May 2015. I was visited with my partner and my parents as we treated them to a Tuscan trip to start the summer. The villa was lovely - simple
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from £59 / night

£446 - £795 / week

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Responds fast!
avg. 2 hours 24 minutes

from £59 / night

23

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £53 / night

£339 - £763 / week

Enquire View

Responds fast!
avg. 42 minutes

from £53 / 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 £194 / night

£1356 - £2434 / week

Enquire View

Responds fast!
avg. 27 minutes

from £194 / night

(10) Excellent 

10

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 £38 / night

£530 - £2206 / week

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from £38 / 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 £66 / night

£450 - £652 / week

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from £66 / night

(8) Excellent 

24

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic Villa and location shame about the weather” The villa was fantastic with extremely hospitable hosts. Grandma provided us with her fantastic home made cake and olive oil. Grandad provided us with home grown beans and lettuce. The Villa is sit
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from £93 / night

£589 - £925 / week

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from £93 / night

(4) Excellent 

21

Holiday apartment in Val d'Orcia

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
“Fantastic experience in a gorgeous setting that exceeded all expectations.” My wife and I spent a week here with our three teenage boys and all of us loved the place. The reality of the home is even better than the photos and we hated to leave. Hosts
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from £229 / night

£1597 - £2017 / week

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from £229 / 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 £34 / night

£236 - £807 / week

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Responds fast!
avg. 1 hour 26 minutes

from £34 / night

(8) Very Good 

14

Apartment rental in Siena

Province of Siena / Siena

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Car not necessary

from £110 / night

£942 / week

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from £110 / night

23

Torre A Castello holiday farmhouse rental

Province of Siena / Torre A Castello

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden

from £170 / night

£1187 - £1441 / week

Enquire View

Responds fast!
avg. 42 minutes

from £170 / night

16

Castellina In Chianti holiday villa rental

Province of Siena / Castellina In Chianti

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £561 / night

£2242 - £3446 / week

Enquire View

from £561 / night

(8) Excellent 

33

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“Excellent with children or groups” We had very enjoyable stay in a peaceful location with stunning views around. Olimpia was very helpful and everything worked as foreseen. We were trying to find a place with a scent of a history and what would suit b
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from £59 / night

£412 / week

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Responds fast!
avg. 1 hour 50 minutes

from £59 / night

14

Holiday farmhouse rental

Province of Siena / San Casciano dei Bagni

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £86 / night

£597 - £841 / week

Enquire View

Responds fast!
avg. 42 minutes

from £86 / 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 £97 / night

£673 - £1051 / week

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from £97 / night

40

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £93 / night

£505 / week

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from £93 / night

1