Province of Siena apartment or villa with a private pool area

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Province of Siena

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911 Holiday homes

Filters applied: Private pool (911)

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

(3) Excellent 

24

Farmhouse rental in Casole d'Elsa with swimming pool

Province of Siena / Casole d'Elsa

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Self-catering Tuscany farmhouse with private pool and garden for al fresco dining. Ideal for families and couples seeking relaxation.  …see more

from £87 / night

£604 - £1466 / week

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from £87 / night

32

Holiday villa rental

Province of Siena / Trequanda

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Villa Leccetino Tuscany Arriving at Leccetino, down a short tree covered road is like arriving at a very secret location. Tucked into the hillside surrounded by olive trees, this is a spectacular masonry villa, made with stones dug up from the ground on this terraced p  …see more

from £492 / night

£3440 / week

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from £492 / night

100

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
This marvelous villa is located in the heart of Tuscany, near the enchanting town of Pienza, and is the ideal villa for anyone looking for a relaxing and peaceful getaway in Tuscany.  …see more

from £370 / night

£2587 - £3449 / week

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from £370 / night

Featured properties

20

Holiday villa in Vagliagli

Castelnuovo Berardenga / Vagliagli

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Solara is a beautiful, modern villa, offering spectacular views of the surrounding countryside. Set within well-kept, private grounds and with easy access to local amenities, the villa is a perfect place for family or cultural holidays.  …see more

from £570 / night

£2280 - £2882 / week

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from £570 / night

24

Villa rental in Siena with swimming pool

Province of Siena / Siena

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This is a stunning eighteenth century villa situated on a hill just 2 kilometres from Siena and enjoying stunning views of the city. With a lovely terrace and informal private outdoor pool overlooking Siena, it's a great setting to enjoy a holiday with family and f  …see more

from £370 / night

£2587 - £3880 / week

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from £370 / night

100

Holiday villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in Tuscany Italy, this gorgeous accommodation is the perfect place for your holidays. The accommodation features: a swimming Pool, air Conditioning .  …see more

from £417 / night

£2919 - £4244 / week

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from £417 / night

(4) Very Good 

14

Province of Siena / Siena

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

 …see more

from £91 / night

£483 - £1061 / week

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from £91 / night

24

Province of Siena / Murlo

4 10 Min stay varies

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

 …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

12

Province of Siena / Cetona

5 6 Min stay varies

  • 5 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 28 km
  • Swimming pool
  • Child friendly

 …see more

from £302 / night

£2113 / week

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from £302 / night

(4) Very Good 

28

Province of Siena / Castellina In Chianti

5 15 Min stay varies

  • 5 bedrooms
  • Sleeps 15
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £186 / night

£1293 - £3431 / week

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from £186 / night

17

Province of Siena / Sarteano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool

 …see more

Pricing unknown

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Pricing unknown

14

Holiday villa with swimming pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This detached house with private garden and pool inside an agricultural business cultivated with olive trees, features also a park and views of Siena and is set in the beautiful Sienese countryside, just 3 km from Vescovado and 5 km from Monteroni away. It consists of t  …see more

from £321 / night

£2242 - £3233 / week

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from £321 / 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
This beautiful, detached stone farmhouse, situated near Castellina in Chianti, was restored in 1995. Surrounded by ample private grounds, it sits in a panoramic position and is reached by its own driveway  …see more

from £561 / night

£2242 - £3446 / week

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from £561 / night

100

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Villa Fiordaliso is perfect for those looking to spend their holiday in a home away from home with stunning views of the Tuscan landscape. Perfect for families and large groups of friends.  …see more

from £432 / night

£3018 - £4095 / week

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from £432 / night

10

Holiday farmhouse in San Fabiano

Monteroni d'Arbia / San Fabiano

4 16 Min stay varies

  • 4 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The Podere Podernovo offers accommodation up to 16 people ,with all comforts,as heating, air conditioning, Internet,wi-fi, Tv with Sky.The Count Fiorentini will welcome you in his farmhouse just 12 km south of Siena in the Arbia valley. You can rent the whole Podere the  …see more

from £466 / night

£2587 - £3449 / week

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from £466 / night

(15) Very Good 

97

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

7 16 1 night min

  • 7 bedrooms
  • Sleeps 16
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
“Wonderful place, we'll come back!” Everything was first class: the rooms, the pool, breakfast, the countryside. We enjoyed a walk in the countryside and had an archery session with a very patient instructor. Staff is very friendly and helpful.  …see more

from £518 / night

£3018 / week

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from £518 / night

(1) Excellent 

12

Holiday farmhouse rental

Province of Siena / Gaiole in Chianti

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
This is a traditional 5 bedroom villa situated between the towns of Gaiole in Chianti and Radda in Chianti. Accommodating up to 18 guests in total as additional apartments are available within the grounds, it's an ideal base for a stay with family or friends. The w  …see more

from £432 / night

£3018 - £4656 / week

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from £432 / night

18

Sarteano holiday villa rental

Province of Siena / Sarteano

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
A quiet country house,(XVIth century), full of atmosphere immersed in the classic Sienese landscape. The swimming pool is beautifully set in a garden and enables you to completely unwind and relax. The interior is well furnished and elegant.  …see more

from £270 / night

£1888 - £4535 / week

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from £270 / night

26

Holiday villa with swimming pool in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The independent holiday villa is located just outside the hamlet and is a recently converted farmhouse.It has a private swimming pool  …see more

from £372 / night

£4557 / week

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from £372 / night

37

Province of Siena / Sinalunga

3 7 Min stay varies

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

 …see more

from £216 / night

£1509 - £2026 / week

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from £216 / night

24

Province of Siena / San Casciano dei Bagni

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

Pricing unknown

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Pricing unknown

52

Holiday villa with swimming pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
The Piaggione of Serravalle, at a first glance, appears as a gem naturally cast on the highest ridges of the Chianti hills of Central Tuscany, and as a jewel it shines with its authentic flavors, ancient traditions and silent stillness. Shaded and enclosed by oak woods  …see more

from £358 / night

£2500 - £4828 / week

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from £358 / 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 £180 / night

£1259 - £1949 / week

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from £180 / night

84

Villa rental in Monticiano with swimming pool

Monticiano / Tocchi

14 27 7 nights min

  • 14 bedrooms
  • Sleeps 27
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
This exclusive luxury villa nestled in the hills of the Tuscan countryside in the south of the province of Siena offers top-quality accommodation completed by first-class services and panoramic views in a natural biogenetic reserve in the Val di Merse.Villa Osse  …see more

from £2744 / night

£19203 - £25604 / week

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from £2744 / night

20

Holiday villa in San Gusme

Castelnuovo Berardenga / San Gusme

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Private viila and swimming pool deeped in nature and quiet.We rent out the whole house,so you could enjoy your holiday without any disturb.  …see more

from £107 / night

£746 - £1194 / week

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from £107 / 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 £475 / night

£1811 - £3595 / week

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from £475 / night

22

Chiusi holiday villa accommodation

Province of Siena / Chiusi

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Villa Baiocco is a typical Tuscan, historic farm house from 1700, recently converted to a prestigious holiday home - without losing its unique character and charm. Surrounded by 20'000m2 of well kept gardens, for your private use only, it offers all the peace and t  …see more

from £246 / night

£1725 - £3880 / week

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from £246 / night

43

Villa letting in Sarteano with swimming pool

Province of Siena / Sarteano

10 17 1 night min

  • 10 bedrooms
  • Sleeps 17
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Tenuta Le Querce is a large estate of about 70 hectares, where biological cultivations are carried out. The houses are surrounded by a vineyard, orchard and an olive grove. We have 2 large houses (450 sqm and 100 sqm) made up in total of : 8 bedrooms with 8 en-suite bat  …see more

from £345 / night

£2414 / week

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from £345 / 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 £338 / night

£2363 - £3328 / week

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from £338 / night

20

Holiday manor house with swimming pool in Pienza

Province of Siena / Pienza

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Tenth century posting house which has kept its charm. Large garden with swimming pool.  …see more

from £646 / night

£4518 - £5647 / week

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from £646 / night

(4) Excellent 

96

Holiday villa in Monticiano

Province of Siena / Monticiano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Ideal family and wedding Tuscan villa with private pool very close to San Galgano Abbey, Siena, Tuscany. Suitable for groups, families and children. Tucked away from the main vuillage, not isolated. All amenities in the village, just 3 minutes' walk away. Siena 25  …see more

from £949 / night

£6466 - £10504 / week

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from £949 / night

12

Apartment rental in Valiano with swimming pool

Montepulciano / Valiano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
It's composed from a stay- kitchen with read couch and fire place, two double bedrooms and a big bath with double console and Jacuzzi. In the stay-kitchen: tv sat.<br />Guests can purchase Vino Nobile di Montepulciano and Extra Virgin Olive Oil from the farm  …see more

from £130 / night

£647 - £819 / week

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from £130 / night

(1) Very Good 

16

Holiday villa with swimming pool, golf nearby in Larniano

San Gimignano / Larniano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Not far from Siena, for 5 minutes along the road from San Gimignano goes towards Gambassi, we find the gates of Villa Panorama.It is an old building of more than 5 centuries and tastefully decorated and with quality furniture and style typical of the villas in Tuscany  …see more

from £216 / night

£1509 - £2156 / week

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from £216 / night

23

Villa rental in Asciano with swimming pool

Province of Siena / Asciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This superb villa with pool in Tuscany is located at 8 km from the pretty medieval village of Asciano, 30 km east of Siena. Surrounded by a private garden full of olive trees, this holiday home has been renovated to an extremely high standard  …see more

from £228 / night

£1595 - £3621 / week

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from £228 / 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 £185 / night

£1121 - £2069 / week

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from £185 / night

(12) Excellent 

70

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 71 km
  • Swimming pool
  • Child friendly
“Wonderful vacation villa!” Our family had a wonderful vacation. Gabrielle and Lucia are so nice and the best hosts. They are always available for anything you might need and willing to provide help in getting to local places. The villa is absolutely  …see more

from £518 / night

£3018 - £7156 / week

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from £518 / night

100

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
This property is a lovely house set in Tuscany Italy. It has 3 bedrooms and 1 bathroom, and it is perfect for those who are looking for a charming holiday. This property features: a swimming Pool .  …see more

from £108 / night

£755 - £1508 / week

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from £108 / night

(5) Excellent 

26

Holiday cottage with swimming pool in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
Charming cottage with private pool and pet-friendly near Siena  …see more

from £62 / night

£432 - £1294 / week

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from £62 / night

(3) Very Good 

21

Sovicille / Torri

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £78 / night

£475 / week

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from £78 / 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
t is a really relaxing apartment: the hall and the kitchen are characterized by green decorations and floral ornaments, whilst a gilt canopy-bed furnishes the big bedroom, where the ceiling is made of stones and beams. Also here the bathroom with shower is made of trave  …see more

from £104 / night

£725 / week

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from £104 / night