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Province of Siena

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804 Holiday homes

(1) Excellent 

16

Holiday home letting

Province of Siena / Monteriggioni

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Il Casale è parte della proprietà denominata Molino Bianco, un antico mulino in pietra documentato fin dall’XI secolo come possedimento della famiglia Lambardi, signori di Staggia. Come annesso del fortilizio di Castiglionalto, il Molino fu abitato da una comunità  …see more

from £112 / night

£701 - £898 / week

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from £112 / 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 £169 / night

£1180 - £2783 / week

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from £169 / night

13

Province of Siena / San Gimignano

5 10 Min stay varies

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

 …see more

from £171 / night

£983 - £2821 / week

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from £171 / night

(3) Very Good 

24

Holiday farmhouse with shared pool in Buonconvento

Province of Siena / Buonconvento

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A unique and enchanting place” We have been going to Tuscany every summer for a while, and are used to renting houses in beautiful properties… We were not expecting to be surprised and overwelmed again by the beauty of a new place. However, Casanova (  …see more

from £257 / night

£1795 / week

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from £257 / night

4

Holiday apartment in San Fabiano

Monteroni d'Arbia / San Fabiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The villa Podernovo offers a nice apartment called Il Forno, with stunning view on the sunflowers fields, with all comforts such air conditioning and heated swimming pool. The apartment Il Forno is at first floor of the villa, with a master bedroom with king size bed,  …see more

from £112 / night

£642 - £855 / week

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from £112 / night

31

Siena / Val di Merse

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 50 km
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £52 / night

£342 - £350 / week

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from £52 / 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 £916 / night

£6411 - £8975 / week

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from £916 / 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 £239 / night

£1253 - £4274 / week

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from £239 / night

(1) Excellent 

16

Villa rental in Chiusi with swimming pool

Province of Siena / Chiusi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Casa Baiocco is a typical Tuscan home, newly built in the traditional farmhouse style, perfectly blending with the Italian countryside. Surrounded by a well kept park, for your private use only, it offers all the peace and tranquility that you look for during your holid  …see more

from £62 / night

£428 - £1325 / week

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from £62 / night

(1) Excellent 

27

Holiday barn with swimming pool in Quercegrossa

Monteriggioni / Quercegrossa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Restored Barn, description: this ground floor flat has an entrance with three large glass doors. The main living area has an open fireplace and is divided into a sitting room and a large kitchen. Dining table, wicker armchairs. Sofa bed for one person. From this room th  …see more

from £82 / night

£445 - £864 / week

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from £82 / night

18

Villa rental in Gaiole in Chianti with swimming pool

Gaiole in Chianti / Montegrossi

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximi  …see more

from £110 / night

£770 - £1966 / week

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from £110 / night

(4) Excellent 

20

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is characterised by good taste and warmth, equipped with a fireplace and elegantly furnished with furniture from the era. Park, scenic swimming pool.  …see more

from £129 / night

£539 - £915 / week

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from £129 / night

(7) Very Good 

22

Province of Siena / Montepulciano

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly

 …see more

from £77 / night

£453 / week

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from £77 / night

(5) Very Good 

15

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

 …see more

from £51 / night

£342 - £558 / week

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from £51 / night

(5) Excellent 

24

Province of Siena / Montepulciano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly

 …see more

from £67 / night

£394 / week

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from £67 / 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 £171 / night

£1539 - £2736 / week

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from £171 / night

(7) Excellent 

25

Province of Siena / Siena

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Child friendly

 …see more

from £81 / night

£496 - £505 / week

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from £81 / night

(1) Average 

4

Province of Siena / Sinalunga

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 25 km
  • Swimming pool

 …see more

from £120 / night

£770 / week

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from £120 / night

(4) Very Good 

24

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Tenuta di Argiano a Montepulciano Please ask always AVAILABILITY , we will find in one of our structures the ideal place for your holiday. CAR IS NECESSARY WE ARE IN THE MIDDLE OF COUNTRYSIDE, SURROUNDED BY NATURE. The beautiful apartment FIASCO (60square Mt) , FOR  …see more

from £60 / night

£419 / week

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from £60 / night

(2) Excellent 

22

Pienza / Monticchiello

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £43 / night

£291 - £375 / week

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from £43 / night

(1) Excellent 

13

Province of Siena / Asciano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £95 / night

£642 - £906 / week

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from £95 / night

20

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £65 / night

£449 / week

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from £65 / night

(34) Excellent 

24

Apartment rental in Val di Merse

Siena / Val di Merse

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly
“What you imagine when you think "Tuscany"!” We stayed in La Verbena, and it was amazing. Podere Sortoiano is about 15 minutes out of Siena, but it is so worth it to stay out of the city! It's incredibly quiet and relaxing, and the stars are unlike any  …see more

from £34 / night

£223 - £366 / week

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from £34 / 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

(2) Excellent 

24

Farmhouse letting in Radda in Chianti

Province of Siena / Radda in Chianti

2 3 5 nights min

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £65 / night

£385 / week

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from £65 / night

(1) Excellent 

12

Province of Siena / Pievescola

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 74 km
  • Child friendly
  • Pet friendly

 …see more

from £77 / night

£539 / week

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from £77 / night

(1) Excellent 

20

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Offers a unique view of the surrounding valley typical of the Sienese hills (olives and grapes) and is located a short distance (3 km) from the town of San Gimignano famous for its medieval towers.  …see more

from £159 / night

£1112 / week

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from £159 / night

(6) Very Good 

34

Radicondoli holiday villa rental

Province of Siena / Radicondoli

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly
Charming independent villa in the heart of Tuscany with panoramic pool, FREE WI FI, garden, parking, wonderful panorama, near Siena, San Gimignano, Florence.Enjoy the real tuscan experience: city tour,food & wine tasting, massage, cooking lesson,horse riding...  …see more

from £300 / night

£1018 - £2265 / week

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from £300 / night

36

Holiday villa in Castelmuzio

Province of Siena / Castelmuzio

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
This little, two-storey, converted Tuscany farmhouse has been meticulously restored in a simple, rustic style, employing high-quality traditional materials. Set on a gentle elevation in a remote spot, it is entirely surrounded by the clay hills called “Crete Senesi”  …see more

from £154 / night

£898 - £1283 / week

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from £154 / night

40

Holiday farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
The watermill “Il Molinaccio”, near the renaissance town of Montepulciano, was already present in the old maps of the Granduchy of Tuscany . The original building, duly and let me say passionately restored, now reopens as a luxury country house where the guests may  …see more

from £95 / night

£513 / week

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from £95 / night

(4) Excellent 

18

Farmhouse rental in Radicofani with shared pool

Province of Siena / Radicofani

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is furnished tastefully and with exclusive period furniture, fireplace, Sky TV, independent heating, external private space. Park, scenic swimming pool.  …see more

from £103 / night

£471 - £727 / week

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from £103 / night

10

Macciano holiday farmhouse rental

Chiusi / Macciano

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Excursions in the nature, the taste, the cities of art and the well-being.The Lands of the province of Sienaoffer one series of distances between art, nature, well-being and gastronomy like perhaps no other place to the world:leaving from Siena, with its ducky beauWiFi  …see more

from £86 / night

£428 - £607 / week

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from £86 / night

(2) Excellent 

63

Villa rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town. A small church with an enchanting bell tower is preserved in its original for  …see more

from £513 / night

£3334 - £3676 / week

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from £513 / night

(3) Excellent 

18

Apartment rental in Siena with shared pool

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Beautiful Tuscan apartment with shared swimming pool, not far from Siena. It sleeps up to 4 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 Se  …see more

from £77 / night

£513 - £941 / week

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from £77 / night

(4) Excellent 

16

Holiday apartment in Radda in Chianti

Province of Siena / Radda in Chianti

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Child friendly
  • Ask about pets
“Very well equipped, comfortable, cosy, beautiful location, lovely owners” My boyfriend and I went to Pornano to stay in June 2013 and had a lovely time. What we wanted We had come to Tuscany as a young couple (23 & 24) with the aim of having a re  …see more

from £50 / night

£350 / week

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from £50 / night

(4) Very Good 

14

Poggibonsi holiday apartment rental

Province of Siena / Poggibonsi

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
While staying in this peaceful property you may enjoy wine tasting from the producers or cooking lessons.  …see more

from £52 / night

£359 - £530 / week

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from £52 / 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 £232 / night

£1624 - £3418 / week

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from £232 / night

(2) Excellent 

34

Radda in Chianti holiday farmhouse rental

Province of Siena / Radda in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Pet friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce organic Chianti Classico wine and extra virgin olive oil.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £52 / night

£274 - £394 / week

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from £52 / night

(11) Excellent 

19

Holiday apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Pet friendly
“Wonderful, Wonderful, Highly Recommended.” My wife and I stayed 23rd. June - 5th. July 2013, and had a wonderful holiday. So relaxing and no hassle whatsoever. The farmhouse has three one bedroomed apartments available and a fourth which Elena (the  …see more

from £73 / night

£449 - £479 / week

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from £73 / night

(6) Very Good 

20

Holiday villa rental

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies at 3 kms from the town of Chianciano Terme, one of the most popular thermal Spas in Italy. The villa is located among the hills dividing Val d'Orcia and Valdichiana. The whole property is for your private use and not shared with any other person. The vill  …see more

from £171 / night

£915 - £2308 / week

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from £171 / night

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