Province of Siena apartment or villa with a private pool area

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Province of Siena

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790 Holiday homes

Filters applied: Private pool

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

(10) Excellent 

58

Holiday villa rental

Province of Siena / San Giovanni d'Asso

8 16 3 nights min

  • 8 bedrooms
  • Sleeps 16
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“unforgettable tuscan paradise” Wonderful historic house, charming atmosphere, you feel at home. We were a group of 16 friends, the house was perfect, nothing was missing. Nice accommodations very clean, housekeeping every day. Unforgettable breakfa  …see more

from £571 / night

£4000 - £5214 / week

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from £571 / night

(1) Very Good 

35

Province of Siena / San Gimignano

7 10 Min stay varies

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

 …see more

from £184 / night

£1283 - £2052 / week

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from £184 / 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
it is the ideal place if you are looking to relax, private pool and beautiful view.  …see more

from £245 / night

£1710 - £3334 / week

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from £245 / night

Featured properties

15

Casole d'Elsa holiday home rental

Province of Siena / Casole d'Elsa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 64 km
  • Swimming pool
  • Child friendly
Situated between San Gimignano and Siena, Villa San Giovanni is a beautiful renovated villa for an extended family or group of friends. The ancient medieval village of Casole d’Elsa is only 3 kilometres away and there are several interesting places within 35 Km. (  …see more

from £117 / night

£812 - £2180 / week

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from £117 / 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
Located between Florence and Siena in Chianti, Villa Gaiole's private hilltop position provides 360 degree panoramic views of the breathtaking Tuscan countryside.  …see more

from £2667 / night

£8890 - £11230 / week

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from £2667 / 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
An ancient farmhouse dating back to 1846 that lies in an agricultural farm that extends over a surface of 150 hectares. Every year our olive grove produces a tasty oil that can be tasted and purchased during your stay.  …see more

from £524 / night

£3667 - £5018 / week

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from £524 / night

34

Sant'Albino holiday villa rental

Montepulciano / Sant'Albino

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves. It has been turned into a residence of refined charm that retains an atmosphere of informal welcome. The landscape and environment of Montepulciano ar  …see more

from £391 / night

£2736 - £5300 / week

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from £391 / night

43

Villa accommodation in Sinalunga with swimming pool, golf nearby

Province of Siena / Sinalunga

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Pet friendly
Description:Old 18th century stone farmhouse restored following the conservation policy that has left the beauty and charm of the past intact. Located between the Val d'Orcia and the hills of the Sienese Chianti, the farmhouse is on two floors: the first floor  …see more

from £223 / night

£1539 - £2009 / week

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from £223 / night

20

Holiday villa rental

Province of Siena / Radicofani

1 12 7 nights min

  • 1 bedroom
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This was an old monastery during the first half of the sixteenth century and went on to become a summer residence for the friars of Monte Oliveto Maggiore. It enjoys beautiful views across a valley. Old farmhouse, well restored, divided into three apartments.  …see more

from £179 / night

£1248 - £1932 / week

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from £179 / 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
The stone farmhouse, probably an old fortified farm, has been completely restored in recent months, using original architectural features and materials. The swimming pool has a waterfall feature and is in a panoramic position.  …see more

from £295 / night

£2060 - £2906 / week

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from £295 / night

37

Province of Siena / Sinalunga

3 7 Min stay varies

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

 …see more

from £223 / night

£1539 - £2009 / week

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from £223 / night

(4) Excellent 

17

Province of Siena / Gaiole in Chianti

2 6 1 night min

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

 …see more

from £103 / night

£513 / week

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from £103 / night

(15) Excellent 

23

Casole d'Elsa holiday villa rental

Province of Siena / Casole d'Elsa

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Villa Podere Scopicciolo is located about 30 miles from Florence. It is 900 ft above sea level in the heart of Tuscany surruonded by cultivated farm land and well preserved forests. It is fully immersed in the countryside enjoying peace and tranquillity, yet convenientl  …see more

from £847 / night

£5924 - £8975 / week

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from £847 / night

29

Villa rental in Siena with swimming pool

Province of Siena / Siena

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
JUST RELAX....YOUR VACATION IN TUSCANY BEGINS NOW!!! Our Villa will be YOUR HOME in Tuscany........... A HOLIDAY WITHOUT THOUGHTS!!! Charming old Villa with 500 years of history, only for your exclusive use, expertly restored offers all modern amenities and comfort enj  …see more

from £240 / night

£1667 - £4274 / week

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from £240 / night

13

Holiday villa with swimming pool in Montalcino

Province of Siena / Montalcino

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Private garden
La Giocosa is located in the most desirable region south of Siena, in the Val d'Orcia, an enchanting and miraculously unspoilt valley in southern Tuscany, listed as UNESCO world heritage in 2004.  …see more

from £611 / night

£4274 / week

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from £611 / night

(1) Excellent 

54

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

 …see more

from £300 / night

£2052 - £4565 / week

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from £300 / night

20

Villa rental in Pienza with swimming pool

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below.  …see more

from £484 / night

£3385 - £4488 / week

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from £484 / night

28

Holiday villa in Pienza

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury Villa near Pienza, ideal for large families or friend's group.  …see more

from £245 / night

£1710 - £5855 / week

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from £245 / night

7

Holiday apartment rental

San Gimignano / Casaglia

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Mimosa is a very nice and cozy apartment on the ground floor of the main villa, with a private entrance.<br />Enfant bed  …see more

from £89 / night

£548 - £812 / week

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from £89 / night

23

Holiday villa accommodation

Province of Siena / Casole d'Elsa

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Lovely farmahouse with private garden & pool in Siena  …see more

from £153 / night

£1069 - £2265 / week

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from £153 / night

59

Province of Siena / Chianciano Terme

6 21 7 nights min

  • 6 bedrooms
  • Sleeps 21
  • 7 nights min
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

 …see more

from £385 / night

£2693 / week

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from £385 / night

27

Province of Siena / Sarteano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £1030 / night

£7210 / week

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from £1030 / night

24

Holiday villa with swimming pool in Castiglione D'Orcia

Province of Siena / Castiglione D'Orcia

8 21 Min stay varies

  • 8 bedrooms
  • Sleeps 21
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful holiday home in the Val d'Orcia, surrounded by gently rolling hills, is near Castiglione d'Orcia (12km), just a few kilometres from the famous spa waters at Bagno Vignoni (10km) and Bagni San Filippo (7km). Surrounded by peace and quiet  …see more

from £471 / night

£1795 - £3565 / week

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from £471 / night

(10) Excellent 

122

Cetona holiday villa rental

Province of Siena / Cetona

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
We can organize typical lunchs or dinners, parties, weddings, cooking lessons, visit to wineries and olive mills taste, babysitting, personal chef etc. We are at your disposal for any request you can have.<br />Free WIFI, Satellite TV, DVD and CD player, dishwash  …see more

from £556 / night

£2394 - £3495 / week

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from £556 / night

16

Province of Siena / Castellina In Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £197 / night

£1197 / week

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from £197 / night

(9) Excellent 

20

San Gimignano holiday villa rental

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about pets
  • Private garden
Naturally cool stone villa for 11 persons with large private pool & gardens in San Gimignano area. Divided into two apartments for 6 and 5 people.  …see more

from £183 / night

£1112 - £2052 / week

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from £183 / 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
The Casale is a very nice private villa, reachable through a dirt road easy to go also with a city car! The villa has a private swimming pool, outdoor BBQ and Jacuzzi, 5 bedrooms and 5 bathrooms (at least 10 people), it also has a big kitchen a big living room with fire  …see more

from £283 / night

£1966 / week

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from £283 / night

20

Farmhouse rental in Siena with swimming pool

Province of Siena / Siena

11 22 2 nights min

  • 11 bedrooms
  • Sleeps 22
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Casa Felice is an outstanding Tuscan farmhouse with 11 bedrooms and 11 bathrooms. It was recently renovated and brought back to its original splendour. Casa Felice is situated on a small road that leads to a wonderful medieval hamlet of Montebenichi.  …see more

from £1352 / night

£5406 / week

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from £1352 / night

18

Holiday villa with swimming pool in Chiusi

Province of Siena / Chiusi

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Monica is a typical Tuscan, farm house from 1700, recently converted to a prestigious holiday home,is surrounded by woods, cultivated fields, olive groves and vineyards  …see more

from £293 / night

£1795 - £2650 / week

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from £293 / night

39

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
JUST RELAX....YOUR VACATION IN TUSCANY BEGINS NOW!!! Our Villa will be YOUR HOME in Tuscany........... A HOLIDAY WITHOUT THOUGHTS!!! Charming old Villa with 500 years of history, only for your exclusive use, expertly restored offers all modern amenities and comfort enj  …see more

from £257 / night

£1795 - £4488 / week

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from £257 / night

24

Holiday villa in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This is a large 10 bedroom villa set over three floors and located at the end of a cypress lined avenue within secluded parkland in the hills of Tuscany. Built in the eighteenth century, the villa is furnished in a style in keeping with the era and has many original his  …see more

from £916 / night

£6411 / week

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from £916 / night

25

Siena holiday villa rental

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies in the hills of southern Tuscany (with a beautiful panorama) around 3 Kms from Radicofani. It forms an ideal starting point for enjoying the peace of the surrounding hills and on the other hand making trips by car (the highway A1 Florence-Rome is 25 Kms f  …see more

from £428 / night

£2052 - £2992 / week

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from £428 / 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
Self-catering Tuscany villa with stunning views, just five minutes walk to the village. Private pool and terrace for al fresco dining. Ideal for families and couples seeking relaxation.  …see more

from £62 / night

£428 - £1710 / week

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from £62 / night

15

Holiday farmhouse rental

Province of Siena / Radicofani

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
We offer hospitality in two delightful double rooms, each with private bath, elegantly furnished exclusively with antique furniture. Each room is accessed directly from the garden with a separate entrance to ensure complete privacy.From the private garden and decora  …see more

from £60 / night

£334 - £445 / week

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from £60 / night

(2) Excellent 

16

Province of Siena / Sinalunga

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

 …see more

from £154 / night

£1018 - £1146 / week

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from £154 / night

19

Holiday cottage with swimming pool in Cetona

Province of Siena / Cetona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Pretty, restored cottage with swimming pool and bowling alley.  …see more

from £335 / night

£2342 - £3300 / week

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from £335 / night

(1) Excellent 

32

Sinalunga / Rigaiolo

4 8 Min stay varies

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

 …see more

from £180 / night

£1257 - £2902 / week

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from £180 / night

(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
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are bea  …see more

from £218 / night

£1526 - £2783 / week

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from £218 / 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  …see more

from £74 / night

£513 - £1496 / week

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from £74 / night

20

Province of Siena / Castellina In Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

 …see more

from £107 / night

£748 / week

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from £107 / night