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

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Siena

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106 Holiday homes

Filters applied: Private pool (106)

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

17

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

 …see more

from £82 / night

£423 - £983 / week

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from £82 / night

(3) Excellent 

22

Villa rental in Siena with swimming pool

Province of Siena / Siena

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level)  …see more

from £345 / night

£1983 - £3449 / week

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from £345 / night

(8) Very Good 

9

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
Best views of Siena.The apartment being only a few minutes from the Campo. The terrace is magnificent with 360°panoramic views of the centre of town, Duomo,the bell tower.It's very quite and you can relax on the roof deck taking a sunbath on the long chair.&  …see more

from £113 / night

£966 / week

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from £113 / night

(3) Very Good 

26

Holiday apartment rental

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Just as expected!” From our first enquiry, the owners were always so helpful and our stay at the Muricce was everything we wanted it to be. This is a wonderful place to stay, and to tour from. There is something to see or to visit in all directions.  …see more

from £82 / night

£449 - £932 / week

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from £82 / night

(2) Excellent 

39

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A charming Tuscan farmhouse villa” We stayed here for a most enjoyable week in September 2016. It is all that the owner Giada describes and she is a charming and helpful host. The villa, a converted stone farmhouse, is located on the outskirts of Sien  …see more

from £113 / night

£759 - £2134 / week

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from £113 / night

19

Siena / Gracciano di Colle Val d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £61 / night

£647 - £906 / week

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from £61 / night

(2) Excellent 

40

Siena / Val di Merse

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £108 / night

£768 - £1897 / week

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from £108 / 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 £432 / night

£2069 - £3018 / week

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from £432 / night

24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
A cypress tree lined road will lead you to Villino Siena and it represents a perfect introduction to this amazing Tuscany villa located just 15 minutes walking from Piazza del Campo, the very heart of Siena. From its privileged hilltop position it enjoys spectacular vie  …see more

from £136 / night

£949 - £2156 / week

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from £136 / night

(2) Excellent 

24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa in Siena with SPA room and swimming pool at exclusive use.  …see more

from £234 / night

£1638 - £3447 / week

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from £234 / night

(3) Excellent 

22

Holiday villa rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Centrum of city only 15 minutes by foot ! The villa was perfectly clean when we arrived. The kitchen is well equipped and fun to cook in.We highly recommend this property for those who are looking for a peaceful setting near all that Siena has to offer.  …see more

from £255 / night

£1078 - £2285 / week

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from £255 / night

100

Holiday villa with swimming pool in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
This lovely cottage has room to accommodate up to 4 people. It boasts a private garden and swimming pool, and it is the perfect house for a family or small group of friends planning a holiday in the countryside.  …see more

from £135 / night

£940 - £1423 / week

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from £135 / night

100

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
This villa is the ideal holiday accommodation for a family or large group with its five bedrooms and bathrooms, lovely gardens and swimming pool, and best of all, its fabulous location just 3km from Siena. Also ideal for weddings and special events.  …see more

from £272 / night

£1897 - £3621 / week

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from £272 / night

34

Province of Siena / Siena

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £173 / night

£1035 / week

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from £173 / night

(6) Very Good 

19

Holiday villa with swimming pool in Siena

Province of Siena / Siena

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
Villa Le Tolfe is so close to Siena you can almost touch it (only 3 kilometres away). With stunning views and beautiful antique gardens this villa is perfect for relaxed stress free holidays. The house is built on top of a hill covered with olive groves and vineyards.  …see more

from £154 / night

£1078 - £2147 / week

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from £154 / night

20

Holiday farmhouse with swimming pool in Iesa

Siena / Iesa

14 27 Min stay varies

  • 14 bedrooms
  • Sleeps 27
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa in Iesa with 14 bedrooms sleeps 27  …see more

from £3291 / night

£19202 - £25604 / week

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from £3291 / night

(4) 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 £78 / night

£414 - £966 / week

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from £78 / 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

20

Siena holiday villa accommodation

Province of Siena / Siena

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Villa Le Cantine di Cerreto is one of our best villas in Italy for rent. Immersed in the heart of the countryside with beautiful swimming pool, this spectacular villa can comfortably sleep up to 14 people and is ideal for your vacation rental in Italy.  …see more

from £2014 / night

£14098 / week

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from £2014 / 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 £259 / night

£1811 - £4526 / week

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from £259 / 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 £242 / night

£1682 - £4311 / week

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from £242 / 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

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 £370 / night

£2587 - £3406 / week

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from £370 / 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

(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 £241 / night

£1682 - £4311 / week

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from £241 / 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 £2681 / night

£8934 - £11285 / week

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from £2681 / 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.<br />A heaven of peace in the heart of the Montagnola  …see more

from £475 / night

£2587 - £4311 / week

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from £475 / 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
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 £850 / night

£3449 - £5949 / week

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from £850 / night

100

Iesa holiday villa accommodation

Siena / Iesa

14 30 7 nights min

  • 14 bedrooms
  • Sleeps 30
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
Perfect for weddings, business meetings or a quiet getaway, Villa Tolomei is on top of a hill with a spectacular view of the verdant Tuscan landscape. Exercise as well as relax while being transported to forgotten places of exquisite taste.  …see more

from £2744 / night

£19203 - £25604 / week

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from £2744 / night

18

Holiday apartment with swimming pool in Caprera

Siena / Caprera

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Recently renovated apartment over two floors, situated on top of the old riding stables, comfortably equipped and elegantly furnished with antique pieces of furniture.  …see more

from £233 / night

£807 - £897 / week

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from £233 / night

10

Province of Siena / Siena

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

 …see more

from £493 / night

£3449 / week

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from £493 / night

(1) Very Good 

12

Holiday villa letting

Province of Siena / Siena

7 14 3 nights min

  • 7 bedrooms
  • Sleeps 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa with swimming-pool just five kilometers from Siena in the middle of Tuscany. Originally a 17th century chapel, Villa del Cielo has been tastefully converted into a charming and unique villa rental in Tuscany.  …see more

from £458 / night

£2785 - £5359 / week

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from £458 / night

24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a spectacular villa set in wonderful Pianella, Pievasciata which is only 14 kms from Siena. Just a short drive from the picturesque town Siena and sitting at the top of one of the rolling hills that are typical of the Tuscan landscape, this magnific  …see more

from £679 / night

£4750 - £5795 / week

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from £679 / night

24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

18 35 7 nights min

  • 18 bedrooms
  • Sleeps 35
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p><span class="x_style25"><span class="x_style25">Total Luxury - Italy special occasion villa with services - this magnificent 14th century estate is situated in the heart of rural Tuscany between San Gimignano and Siena. The villa  …see more

from £6069 / night

£42480 - £53850 / week

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from £6069 / night

49

Province of Siena / Siena

6 10 Min stay varies

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

 …see more

from £302 / night

£1871 - £7792 / week

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from £302 / night

32

Holiday villa with swimming pool in Siena

Province of Siena / Siena

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • 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 en  …see more

from £272 / night

£1897 - £4742 / week

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from £272 / night

46

Province of Siena / Siena

3 7 Min stay varies

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

 …see more

from £216 / night

£1552 - £2026 / week

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from £216 / night

(4) Excellent 

40

Province of Siena / Siena

2 4 7 nights min

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

 …see more

from £109 / night

£763 - £1246 / week

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from £109 / night

(1) Excellent 

31

Province of Siena / Siena

3 7 Min stay varies

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

 …see more

from £190 / night

£1328 - £2113 / week

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from £190 / night

8

Province of Siena / Siena

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly

 …see more

from £81 / night

£561 - £1164 / week

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from £81 / night