Province of Siena apartment or villa with a private pool area

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Province of Siena

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900 Holiday homes

Filters applied: Private pool (900)

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
An eighteenth century Tuscan farmhouse in a delightful little valley along the historic Via Francigena, surrounded by 14 hectares of privately owned vines, olive trees and woods that ensure utter privacy and tranquillity.  …see more

from £836 / night

£3390 - £5848 / week

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from £836 / night

(2) Excellent 

16

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

 …see more

from £73 / night

£399 - £950 / week

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from £73 / 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 wonder  …see more

from £424 / night

£2967 - £4577 / week

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from £424 / night

36

Holiday villa in Siena

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Beautiful Tuscan Villa with swimming pool, not far from Siena. It sleeps up to 22 guests. It is an ideal place for families to spend a relaxing holiday far from town noises, among the peace of the countrside.A heaven of peace in the heart of the Montagnola Senese, at a  …see more

from £467 / night

£2543 - £4238 / week

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from £467 / night

(6) Excellent 

21

Villa rental in Montisi with swimming pool

Province of Siena / Montisi

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A beautifully restored fully air-conditioned 16th century village house, filled with antiques. There are 4 bedroom/5 bath with stunning views, a garden overlooking the stunning Tuscan countryside, and a pool. Groceries, gelato and the best coffee within yards - and a fu  …see more

from £260 / night

£1650 - £2720 / week

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from £260 / night

(5) Excellent 

16

Farmhouse rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
TUSCANY (Montepulciano) PODERE SAN PIETRO, ancient country house recently restored, with 3 bathrooms, 4 bedrooms (max 10 sleepers), provided of private swimmingpool, fenced garden 3000 sq.m. Medium and small size pets are allowed.  …see more

from £170 / night

£1187 / week

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from £170 / night

23

Province of Siena / Radicondoli

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 56 km
  • Swimming pool
  • Child friendly

 …see more

from £303 / night

£2119 / week

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from £303 / 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
Villa Gaiole features all the comforts and a wonderful panoramic Tuscan Villa in Chianti between Siena and Florence, with private pool, air conditioning, total privacy, and a lovely park.  …see more

from £390 / night

£2712 - £3814 / week

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from £390 / 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
The large 800 sqm villa is an ancient historical residence. Villa Siena, an 18th century villa, rises within a se cluded parkland in the hills of Tuscany. The theme of the outdoors continues in the elegant drawing room, formerly a ballroom, whose vaulted ceiling and wal  …see more

from £576 / night

£4026 - £6145 / week

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from £576 / night

21

Apartment rental in Casole d'Elsa with swimming pool

Province of Siena / Casole d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Apartment in a detached building consisting of two double bedrooms, bathroom, kitchen with fridge, microwave,stove, living room with sofa bed for two additional seats, furnished outdoor living room.By adding two more people to contact for price.The price is per apartmen  …see more

from £85 / night

£484 - £763 / week

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from £85 / night

(1) Excellent 

24

Holiday villa with swimming pool in Poggibonsi

Province of Siena / Poggibonsi

7 18 7 nights min

  • 7 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful villa with pool in Chianti is located near the town of Poggibonsi, surrounded by the gently rolling hills of this beautiful region. The accommodation is on two floors and can comfortably accommodate up to 18 people. Accommodation, 400 sqm : GROUND FLOOR  …see more

from £234 / night

£1636 - £3941 / week

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from £234 / 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 £424 / night

£2967 - £4026 / week

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from £424 / night

100

Holiday villa in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
This villa offers 8 bedrooms to accommodate up to two people each. They all have their own en-suite bathroom, and they share a beautiful dining room, two living areas, kitchen, covered patio and a fabulous garden with swimming pool.  …see more

from £462 / night

£3221 - £4662 / week

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from £462 / 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 £194 / night

£1356 - £2119 / week

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from £194 / night

(3) Excellent 

24

Radicondoli / Belforte

4 9 Min stay varies

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

 …see more

from £183 / night

£1272 - £1865 / week

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from £183 / night

24

Villa rental in San Giovanni d'Asso with swimming pool

Province of Siena / San Giovanni d'Asso

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p><span class="x_style25">Centred around a pretty garden, Casa Vittorio is a notable, historic residence set over several levels and elegantly furnished. It is in a village location, just a short stroll from a restaurant, the castle and the truffl  …see more

from £713 / night

£4990 - £6090 / week

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from £713 / night

100

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 £247 / night

£742 - £1483 / week

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from £247 / 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

£297 - £441 / week

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from £60 / night

22

Holiday tower with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
Stunning medieval tower near San Gimignano for holiday rentals  …see more

from £122 / night

£848 - £2077 / week

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from £122 / 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 £424 / night

£2034 - £2967 / week

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from £424 / night

11

Torrita di Siena / Montefollonico

3 6 1 night min

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

 …see more

from £51 / night

£356 / week

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from £51 / 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 £182 / night

£1102 - £2034 / week

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from £182 / night

25

Province of Siena / Gallina

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £136 / night

£950 / week

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from £136 / night

100

Holiday villa with swimming pool, tennis court in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in Tuscany Italy, this stunning accommodation is the perfect place for your holidays. The accommodation offers: a swimming Pool, air Conditioning, a pet friendly space .  …see more

from £1556 / night

£10897 - £15739 / week

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from £1556 / 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 £1022 / night

£7149 / week

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from £1022 / night

(2) Excellent 

24

Province of Siena / Palazzone

4 10 Min stay varies

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

 …see more

Pricing unknown

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Pricing unknown

(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  …see more

from £231 / night

£1611 / week

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from £231 / night

(1) Excellent 

36

Province of Siena / Gaiole in Chianti

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £364 / night

£2543 - £3814 / week

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from £364 / night

16

Contignano holiday villa rental

Radicofani / Contignano

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The exquisite villa is located in Contignano surrounded by spectacular views of rolling clay hills and countryside. The villa sleeps up to 19 in 8 very spacious bedrooms, 2 twins, 5 doubles and a lofted bedroom containing a sofa bed, a twin and a double bed  …see more

Pricing unknown

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Pricing unknown

100

Holiday villa in Castiglione D'Orcia

Province of Siena / Castiglione D'Orcia

8 19 7 nights min

  • 8 bedrooms
  • Sleeps 19
  • 7 nights min
  • Swimming pool
  • Child friendly
This property in Tuscany Italy is a stunning house that sleeps 19 people, so it is perfect for large families. The accommodation offers the following: a swimming Pool, an internet Connection, a pet friendly space, disabled access .  …see more

from £277 / night

£1936 - £3564 / week

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from £277 / night

30

Montepulciano holiday watermill rental

Province of Siena / Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 16 km
  • Swimming pool
  • Child friendly
Beutiful old structure located in one of the most unspoiled place in Tuscany. Peace and relax. Private garden with swimming pool , wifi, and inside parking. Villa for 6 people and another annex , for 4 people , is ideal for family or friends groups for a total of 10 p  …see more

from £145 / night

£950 - £3111 / week

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from £145 / night

24

Holiday villa in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
"Villa Palazzone" is a charming country house set in the heart of a large estate of 153 hectares. The property has been completely renovated and upgraded with all modern conveniences.  …see more

from £276 / night

£1687 - £2839 / week

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from £276 / night

22

Province of Siena / San Gimignano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Ask about pets

 …see more

from £184 / night

£1289 - £1530 / week

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from £184 / 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 £178 / night

£1246 - £2878 / week

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from £178 / 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 £212 / night

£1484 - £1992 / week

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from £212 / night

23

Murlo holiday villa rental

Murlo / Casciano di Murlo

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Villa San Donato gives you the unique chance to stay in a residence that was once an ancient church! It is completely refurnished and turned into a beautiful villa, which offers you an unforgettable time in Tuscany.  …see more

from £250 / night

£1746 / week

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from £250 / night

26

Villa rental in Sant'Albino with swimming pool

Montepulciano / Sant'Albino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano. The property is situated in the heart a working farm with breathtaking views over the valley where Vino Nobile di Montepulciano is produced. The villa ha  …see more

from £231 / night

£1611 - £3051 / week

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from £231 / night

28

Holiday apartment in Quercegrossa

Monteriggioni / Quercegrossa

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Villa is situated in a splendid 18th century mansion, with typical Sienese architecture. The property position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena (6 km away).The mansion is s  …see more

from £89 / night

£594 - £1602 / week

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from £89 / night

100

Holiday villa with swimming pool in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
This pleasant house, with 6 bedrooms and 6 bathrooms can host 12 people, so it is perfect for a large group of friends. Located in Lazio Italy, this house offers a swimming Pool, an internet Connection, a pet friendly space, disabled access .  …see more

from £356 / night

£1373 - £2975 / week

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from £356 / night

110

Siena holiday villa rental

Province of Siena / Siena

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Villa Nuti is an elegant XVII century manor only 3 km from the center of Siena, the bus stop to the centre is 400 meters from the villa. From its unique terrace it enjoys privileged magnificent views of the town with its famous bell towers. The villa has been completel  …see more

from £364 / night

£2543 - £3348 / week

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from £364 / night

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