Province of Siena apartment or villa with a private pool area

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Province of Siena

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826 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.

24

Holiday villa letting

Province of Siena / Castellina In Chianti

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Everything about this property is classically Tuscan. If you dream of typical Tuscany as breathtaking panoramas, misty hills covered in precision lines of vineyards, olive groves, gravel roads and driveways shadily lined with pointy cypress trees, and grand villas with  …see more

from £563 / night

£3941 / week

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from £563 / night

32

Farnetella holiday villa rental

Sinalunga / Farnetella

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Beautiful and characteristic villa made of stone and bricks and completely restored to be a welcoming holiday home, situated on the green hills of the Siena countryside, 6 km far from the village of Sinalunga endowed with every kind of shops and services.  …see more

from £170 / night

£1187 - £2204 / week

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from £170 / night

(5) Excellent 

22

Apartment rental in Monteriggioni with swimming pool

Province of Siena / Monteriggioni

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Casa Laura is an independent apartment in a restored farmhouse Agriturismo la Magione that is situated on an agricultural estate on a hilltop at about 300 meters above sea level. It offers a wonderful panorama of the surrounding countryside with fields, olive groves, vi  …see more

from £60 / night

£382 - £471 / week

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from £60 / night

Featured properties

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

(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!  …see more

from £97 / night

£678 - £1060 / week

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from £97 / 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 £60 / night

£636 - £890 / week

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from £60 / night

(7) Very Good 

24

Villa letting in Poggibonsi with swimming pool

Province of Siena / Poggibonsi

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“On top of the mountain...” When driving on the driveway of the property domain we were astonished by the fantastic viewpoint on tuscan hills and vineyard on the domain. The house was clean and offered all the facilities as expected...swimming pool...B  …see more

from £204 / night

£1399 - £2331 / week

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from £204 / night

(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 £567 / night

£3967 - £5170 / week

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from £567 / 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 £77 / night

£407 - £950 / week

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from £77 / night

23

Province of Siena / Gallina

2 6 Min stay varies

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

 …see more

from £136 / night

£950 / week

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from £136 / 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 £467 / night

£2543 - £4238 / week

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from £467 / night

(4) Very Good 

33

Holiday apartment with swimming pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Just 1800 mt from the historical centre of San Gimignano, along the Francigena road, you will find a place where you can spend beautiful Tuscany holidays. The apartment is located in the countryside of the medieval town, in the centre of Tuscany. The house is surround  …see more

from £45 / night

£339 - £721 / week

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from £45 / 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 £382 / night

£2670 / week

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from £382 / 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 £2697 / night

£18878 - £25170 / week

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from £2697 / 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 £231 / night

£1611 - £3389 / week

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from £231 / 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 £111 / night

£746 - £2204 / week

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from £111 / night

(1) Excellent 

19

Holiday farmhouse in San Gimignano

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“Very good appartment, with great views” We stayed in Podere Le Monache 4 for one week in August. It was more then we expected from the pictures and the description. The appartment was very clean and spacious, with two large bedrooms and enough furnitu  …see more

from £64 / night

£424 - £933 / week

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from £64 / 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 £102 / night

£712 / week

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from £102 / night

100

Holiday villa with swimming pool in Montalcino

Province of Siena / Montalcino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
This villa provides guests with a panoramic pool, a living room, a fully equipped kitchen, a study room, four double bedrooms and three bathrooms.  …see more

from £509 / night

£3560 - £4831 / week

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from £509 / night

(7) Excellent 

24

Val d'Orcia holiday villa rental

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
One of three unique and charming apartments in a XVI century villa situated in the wonderful senese countryside a few km's from Montalcino, in the natural park of the Val d' Orcia, a precious architectural and natural context.Here you will feel embraced by  …see more

from £231 / night

£1611 - £2039 / week

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from £231 / night

17

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Small farmhouse with swimming pool which can be covered.  …see more

from £122 / night

£848 - £1458 / week

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from £122 / night

100

Holiday villa rental

Province of Siena / Montepulciano

5 13 7 nights min

  • 5 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
charming accommodation sleeps 13 people, so it is perfect for large families and is located in Tuscany Italy. This property is ideal if you seek a unique experience. The villa offers: a swimming Pool, a pet friendly space .  …see more

from £141 / night

£984 - £2183 / week

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from £141 / night

20

Holiday manor house rental

Province of Siena / Chiusi

8 21 7 nights min

  • 8 bedrooms
  • Sleeps 21
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool
This large country house, located in the hills between Lake Chiusi and Lake Trasimeno is an ideal property for a large family or a group of friends that which to spend their holidays together in the beautiful Tuscan countryside.This property is particular suitab  …see more

from £302 / night

£2111 - £3162 / week

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from £302 / 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

(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 £509 / night

£2967 - £7034 / week

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from £509 / 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 £250 / night

£1060 - £2246 / week

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from £250 / 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 £243 / night

£1695 - £3306 / week

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from £243 / night

(14) Excellent 

24

Holiday villa in San Gimignano

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“If only we could live here!” We spent the 1st 2 weeks of June here with 7 of us in total, 6 adults 1 child. The property is fantastic, it has all the facilities you want with huge rooms. We didn't realise that 2 of the rooms were adjoining which was a  …see more

from £170 / night

£1526 - £2712 / week

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from £170 / night

20

Holiday home in Buonconvento

Province of Siena / Buonconvento

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully restored 14th century farmhouse sits within a farming estate on a hilltop with magnificent views over the soft hills of the Arbia river valley.  …see more

from £938 / night

£3751 - £6057 / week

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from £938 / night

(1) Excellent 

13

Monteriggioni holiday villa rental

Province of Siena / Monteriggioni

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Private garden
Is the perfect mix of luxury and rustic Italian, with a relaxed feel perfect for a holiday with friends and family or for a special celebration! Stomennano's got so much character and charm and you'll be amazed by the beauty of the Villa and the gardens.  …see more

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22

Holiday villa rental

Colle di Val d'Elsa / Campiglia dei Foci

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Villa Nr. San Gimignano, Siena Province, Tuscany, Italy Typical Tuscan Style Villa with Private Pool and Large Private garden. 12.000 Square Metres Of Gardens, With Pine Trees, Monumental Oaks And Olive Grove Wonderful stone building situated in a peaceful position wit  …see more

from £136 / night

£1484 - £2543 / week

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from £136 / night

41

Pienza / Monticchiello

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £149 / night

£1017 - £1187 / week

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from £149 / night

(16) Excellent 

22

Casole d'Elsa holiday cottage rental

Province of Siena / Casole d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly
“Everything we wanted: excellent villa with lovely pool, beautiful countryside views and welcoming owners.” La Casa Dei Nonni was above and beyond our expectations. The location within the Tuscan hillside village of Monteguidi was easy to find from the  …see more

from £128 / night

£763 - £1145 / week

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from £128 / 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 £551 / night

£2373 - £3465 / week

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from £551 / night

15

Province of Siena / Radicofani

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £68 / night

£382 / week

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from £68 / night

100

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in Tuscany Italy, this charming villa is the ideal place for your holidays. The villa offers: a swimming Pool, air Conditioning, an internet Connection .  …see more

from £364 / night

£2543 - £6611 / week

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from £364 / night

(12) Very Good 

28

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Villa PetrAlexa - excellent leisure facility” This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfec  …see more

from £175 / night

£1221 - £2034 / week

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from £175 / night

(2) Very Good 

29

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
.This charming accommodation lies in the countryside enjoying the most marvellous views of the undulating landscape and the towers of the city of San Gimignano only 3km away. It is a lovely location for enjoying country walks and relaxing<br />The pool and the gar  …see more

from £170 / night

£1187 - £1780 / week

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from £170 / night

(30) Excellent 

26

Holiday farmhouse with swimming pool in Val d'Orcia

Montalcino / Val d'Orcia

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
“Great Location” We can only reiterate the excellent reviews that have gone before. Fonte Aulente is in a great location, quiet and secluded with amazing views of the Tuscan countryside and close to the beautiful town of Montalcino. The accommodation,  …see more

from £102 / night

£712 / week

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from £102 / night

(14) Excellent 

24

San Gimignano holiday villa rental

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
“Beautiful!” Four of us stayed here in October 2012, the house is beautiful and immaculately maintained as are the gardens. Unfortunately the weather wasn't on our side so we didn't spend as much time in the garden as we'd have liked but you could spe  …see more

from £68 / night

£467 - £1526 / week

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from £68 / night