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142 Holiday homes

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

(22) Excellent 

18

Elegant 2 bedroom apt. in historic Siena residence - Siena apartment sleeps 5

Province of Siena / Siena

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
Historic Residence Palazzo Bichi Ruspoli is situated on the main street, in the heart of Siena. The entrance is from the ancient tower, one of the three buildings wich the palace is composed. The house is on the third floor with elevator and has a stunning view on the c  …see more

from £134 / night

£871 - £1962 / week

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from £134 / night

(8) Very Good 

5

TuscanFlat - Siena apartment sleeps 4

Province of Siena / Siena

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Nearest beach 105 km
  • Car not necessary
  • Air conditioning
This very stylish 430-square-foot apartment a few minutes walk from Piazza del Campo.You will need to walk up 66 steps to access this apartment, but the effort is amply rewarded by two amazing terraces and their spectacular views. The main living space here is a large,  …see more

from £87 / night

£664 - £966 / week

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from £87 / night

(2) Very Good 

20

Luxury apartment in Siena, Tuscany - Siena apartment sleeps 4

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Luxury apartment which has been carefully restored, frescoed ceilings and walls, equipped with every comfort, set a short walk from Piazza del Campo, the square of the worldwide Palio of Siena. The apartment is located on the third floor of historical palace in the live  …see more

from £130 / night

£776 / week

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from £130 / night

(33) Excellent 

24

SORTOIANO apartaments in historic Tuscan property - Val di Merse apartment sleeps 5

Siena / Val di Merse

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly
LAST MINUTE OFFER IN SEPTEMBER !! OFFERTE LAST MINUTE A SETTEMBRE !! FURTHER AVAILABILITY DESPITE THE BOOKING CALENDAR, PLEASE, LET'S CONTACT US! The property dates back to the 14th century and for generations has been part of the property Santini, once farmers. The  …see more

from £39 / night

£259 - £302 / week

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from £39 / night

(4) Excellent 

14

Apartment in the historic city center of Siena - Siena house sleeps 4

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Ask about pets
This bright and modern apartment totally renovated by just one year, is situated in the charming historic centre of Siena.The apartment is part of a palace complex with other apartments and is located on the ground floor and consists of two floors.The apartment is so co  …see more

from £82 / night

£561 / week

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from £82 / 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 £69 / night

£500 - £509 / week

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from £69 / night

(5) Excellent 

36

Sharing Cozy Rooms in Tuscany 20km from Siena - Siena guest house sleeps 4

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Child friendly
  • Private garden
My Cottage is situated on top of a hill in a forest where peace and quiet of the Tuscan countryside are the characteristics. If you love the nature you will definitely love my place. The area is perfect for biking and hiking. Explore the surroundings with a castle, a ro  …see more

from £44 / night

£302 / week

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from £44 / night

(6) Very Good 

24

Villa Caprera. Casa Borgianni - Caprera farmhouse sleeps 6

Siena / Caprera

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning
A stylish apartment close to Siena ancient city walls, still surrounded by olive groves and fields; ideal for visitors looking for a quite lodge. The farmhouse is part of a unique Liberty village built by Garibaldi's doctor in 1880. Local shops are at walking dista  …see more

from £130 / night

£845 - £1078 / week

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from £130 / night

(6) Excellent 

56

Villa di Geggiano - Siena guest house sleeps 4

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning
One of the original, charming and elegant garden pavilions, situated within the garden of Villa di Geggiano, has recently been renovated into two luxury suites which have now been opened to guests for reservation. The Pavilion has a total capacity of 4 persons but it  …see more

from £388 / night

£2371 / week

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from £388 / night

(1) Excellent 

39

Bright, spacious villa with pool near Siena - Siena villa sleeps 7

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Key points: large apartment (140 m2) in a farmhouse renovated with taste and attention to details. Terrace and independent entrance into the courtyard of the property, large pool with view and garden-park with olive grove. Fully equipped kitchen, comfortable living room  …see more

from £156 / night

£845 - £1302 / week

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from £156 / 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) Excellent 

16

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from £250 / night

£1716 - £9052 / week

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from £250 / night

(1) Excellent 

18

Province of Siena / Siena

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Air conditioning

 …see more

from £78 / night

£475 - £656 / week

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from £78 / night

36

Beautiful Tuscan Villa not far from Siena 22 pax - Siena villa sleeps 22

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • 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) you will  …see more

from £475 / night

£2587 - £4311 / week

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from £475 / night

30

Cozy Cottage in Tuscany 20km from Siena sleeps 4 - Siena house sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 100 km
  • Child friendly
  • Private garden
Only 20km outside the charming city of Siena, my cottage is emerging in a beautiful forest on top of a hill. Ideal for biking and hiking. Perfect for relaxing holidays or for a working context. WiFi-connection. A picturesque mosaic of fields and vineyards are breath-t  …see more

from £50 / night

£388 - £509 / week

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from £50 / night

(3) Excellent 

22

Beautiful tuscan Villa not far from Siena 18 pax - Siena villa sleeps 18

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) you will  …see more

from £345 / night

£1983 - £3449 / week

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from £345 / night

(2) Excellent 

12

LA VERBENA self-catering country house in Tuscany - Val di Merse farmhouse sleeps 4

Siena / Val di Merse

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
OFFER IN JULY !!! The property PODERE SORTOIANO dates back to the 14th century and for generations has been part of the property Santini, once farmers. The apartments, as well as the "hut" were once stables for livestock. It has now been restored by the Santini family  …see more

from £40 / night

£250 - £370 / week

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from £40 / night

(42) Excellent 

35

Beautiful Private Villa, pool, hot tub,wi-fi,Siena - Siena villa sleeps 12

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
JUST RELAX...... YOUR VACATION IN TUSCANY BEGINS NOW!!!! What we want is to make this holiday as pleasant and relaxing as possible, so we want to make available to you our Villa, that for a time, long or short it might be, will be YOUR HOME in Tuscany. A HOLIDAY WITHOUT  …see more

from £241 / night

£1682 - £4311 / week

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from £241 / night

(3) Excellent 

22

SIENA,villa,pool,tennis,relax,near Piazza IL CAMPO - Siena villa sleeps 5

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
La villa (5 posti letto ) è situata nella campagna di Siena a circa 15 minuti a piedi dalla famosa 'Piazza del Campo' di Siena. Si trova in cima ad una collina, corredata di piscina e campo da tennis, offre splendidi panorami sulla città e sulla campagna cir  …see more

from £255 / night

£992 - £1725 / week

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from £255 / night

(3) Excellent 

18

Apartment Camilla, countryside, not far from Siena - Siena apartment sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • 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) you will  …see more

from £78 / night

£518 - £949 / week

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from £78 / night

24

23916-Holiday house San Gimign - Badia A Elmi villa sleeps 8

Siena / Badia A Elmi

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The property is a beautiful detached villa converted from a lovely, old hay store situated in the Chianti hills half way (35 km) between Florence and Siena. In the well kept garden there is an inviting swimming pool (8 x 5 m) available from May to October opening onto  …see more

from £94 / night

£652 - £1410 / week

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from £94 / night

8

Province of Siena / Siena

3 2 1 night min

  • 3 bedrooms
  • Sleeps 2
  • 1 night min

 …see more

from £69 / night

£345 / week

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from £69 / night

4

Magica Toscana immersed in nature in Chianti - Siena b&b sleeps 4

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Private garden
In the heart of Tuscany, in the silence of nature among woods and vineyards of the Chianti region, in a dominant position and sunny, sunsets and beautiful landscapes, possibility 'of trekking on foot and horseback tours.The rooms are equipped with a double bed or  …see more

from £65 / night

£453 / week

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from £65 / night

22

Villa Gaiole - Siena villa sleeps 13

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. Set around an expansive central courtyard with barbeque area, this luxury villa rental provides visito  …see more

from £2560 / night

£8534 - £11378 / week

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from £2560 / night

29

Siena holiday apartment rental - Siena apartment sleeps 2

Province of Siena / Siena

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Located just outside the walls of the historical center, with a 900 square meters private garden and a 30000 square meters private park, 7 minutes walk from Piazza del Campo, 3 minutes walk from Piazza San Francesco, this charming holiday accommodation has been totally  …see more

from £91 / night

£453 / week

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from £91 / night

(2) Excellent 

19

PALAZZO GIORGI Suite in Piazza del Campo, Siena - Siena apartment sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Child friendly
  • Air conditioning
The apartment overlooks the beautiful Piazza del Campo , with a light coming from the three main windows and invades the entire house is unique about every hour of the day . The apartment has just been renovated and furnished with designer pieces and equipped with every  …see more

from £250 / night

£1638 - £2156 / week

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from £250 / night

(2) Excellent 

35

Province of Siena / Siena

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from £70 / night

£483 - £1087 / week

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from £70 / night

18

BELLAVALLE - Siena villa sleeps 10

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 – this is Bellavalle, just 3.5 kilometres from  …see more

from £850 / night

£3535 - £5949 / week

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from £850 / night

12

10319 - Villa Dan - Gracciano di Colle Val d'Elsa villa sleeps 10

Siena / Gracciano di Colle Val d'Elsa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Pet friendly
Villa Dan is located between the cities of Arezzo, Florence and Siena, at the quaint old town of Figline Valdarno with its ancient piazza and historical buildings. The Villa Dan has 5 bedrooms and 3bathrooms, situated in Figline Valdarno, with a magnicificient view. On  …see more

from £358 / night

£2500 / week

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from £358 / night

24

Tenuta Val d'Elsa - Siena villa sleeps 35

Province of Siena / Siena

18 35 7 nights min

  • 18 bedrooms
  • Sleeps 35
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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's hilltop position offers wonderful 360 degree views of the surrounding countryside  …see more

from £4526 / night

£31680 - £45500 / week

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from £4526 / night

25

Apartment GAIA, countryside, not far from Siena - Siena apartment sleeps 10

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • 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) you will  …see more

from £207 / night

£1207 - £1983 / week

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from £207 / night

23

Province of Siena / Siena

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Pet friendly

 …see more

from £285 / night

£544 / week

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from £285 / night

24

23891-Holiday house San Gimign - Badia A Elmi villa sleeps 5

Siena / Badia A Elmi

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
Charming stone-built house located in a peaceful and panoramic position on the green, rolling hills near San Gimignano. The villa is the result of a recent renovation which has transformed this ancient barn into a beautiful and comfortable detached villa, ideal for spe  …see more

from £84 / night

£587 - £1586 / week

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from £84 / night

30

Beautiful Private Villa,Pool,Hot tub, Wi-Fi, Siena - Siena villa sleeps 13

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 en  …see more

from £259 / night

£1811 - £4526 / week

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from £259 / night

27

Charming private Villa,Pool,Hot tub,Wi-Fi, Siena - Siena villa sleeps 10

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 en  …see more

from £242 / night

£1682 - £4311 / week

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from £242 / night

20

Casa Felice - Siena farmhouse sleeps 22

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.The villa is filled w  …see more

from £1352 / night

£5406 - £5822 / week

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from £1352 / night

45

Province of Siena / Siena

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £122 / night

£854 - £863 / week

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from £122 / night

9

Villa Siena 2-4 persons - Siena apartment sleeps 4

Province of Siena / Siena

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
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 £156 / night

£845 - £949 / week

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from £156 / night

26

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Ask about pets

 …see more

from £173 / night

£690 - £1121 / week

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from £173 / night

(1) Excellent 

17

Province of Siena / Siena

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £104 / night

£725 / week

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from £104 / night

Top Destination reviews

La Stalla di San Lazzero, adorable house in Siena
What a wonderful stay! We highly recommend this house!

We instinctively felt in love with Leonardo's house the moment we arrived! The description we received from Leonardo how to get to the house was perfect and we immediately found the correct way (thank you!). Leonardo greeted us warmly and showed u … see more
Private, elegant zen cottage, 10 min. from Siena
Peaceful cottage in isolated location

Property although in an isolated location was fairly central for accessing all of the Tuscany region. All points requiring access were never any more than 1 hours drive away. Great base for touring. Property has no air conditioning therefore reli … see more

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