Horse riding holiday villas and apartments Province of Siena | Holiday Lettings

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  • Asciano (33)
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1,075 Holiday homes

Filters applied: Horse riding (1,075)

(30) Excellent 

1 / 25

Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool

San Gimignano / Castel San Gimignano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
The apartment is located in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the oliv  …see more

from £84 / night

£459 - £709 / week

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from £84 / night

(18) Excellent 

1 / 49

3 bedroom holiday apartment near Tuscan cities, staffed property with outdoor pool

San Gimignano / Castel San Gimignano

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
The apartment is placed in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the olive  …see more

from £84 / night

£459 - £709 / week

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from £84 / night

(2) Excellent 

1 / 18

Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 27 nights min stay

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Pets welcome;
 …see more

from £75 / night

£525 - £800 / week

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from £75 / night

(1) Excellent 

1 / 14

New Casa Titta apt 3 bedrooms , amazing view

San Gimignano / Castel San Gimignano

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 55 km; Great for children of all ages ; Car advised;
C asa Titta is our third apartment ,completely new ,really comfortable, placed on the first floor with three bedrooms for 5 people and a large open space living . A new kitchen equipped with dishwasher , fridge/freezer, microwave and electrical hoven. The bathroom has  …see more

from £84 / night

£459 - £709 / week

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from £84 / night

1 / 24

Province of Siena / Pienza

1 bedroomSleeps 35 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 5 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
 …see more

from £105 / night

£0 / week

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from £105 / night

(11) Excellent 

1 / 21

charming cottage in peaceful country setting

Montepulciano / Gracciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 90 km; Swimming pool; Great for children of all ages ;
The cottage is opposite the owner's house and consists of two double bedrooms, two bathrooms and a large living room with cooking area. The living area opens onto a patio and pergola and the downstairs bedroom also opens onto a small patio. There is access for the disa  …see more

from £67 / night

£384 - £1717 / week

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from £67 / night

1 / 28

Holiday lodging near Pienza P5 - Torrita di Siena apartment sleeps 5

Province of Siena / Torrita di Siena

1 bedroomSleeps 57 nights min stay

  • 1 bedroom
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £44 / night

£305 - £575 / week

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from £44 / night

(9) Very Good 

1 / 31

Le Fontanelle - rustic farm buildings with pool

Province of Siena / San Gimignano

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
Nestled in a centuries-old complex of farm-house buildings, just 10 minutes drive from the medieval "skyscraper" fortress town of San Gimignano...Le Fontanelle is the perfect place to soak in Tuscany's sunshine, culture, food and fun.An easy drive from Pi  …see more

from £96 / night

£596 - £788 / week

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from £96 / night

1 / 22

Holiday Apartments near Pienza - Torrita di Siena farmhouse sleeps 3

Province of Siena / Torrita di Siena

1 bedroomSleeps 37 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £34 / night

£234 - £492 / week

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from £34 / night

1 / 36

Villa Le Crete - Castelmuzio villa sleeps 6

Province of Siena / Castelmuzio

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
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 £150 / night

£875 - £1250 / week

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from £150 / night

1 / 20

Villa Olmo - Radicofani villa sleeps 14

Province of Siena / Radicofani

7 bedroomsSleeps 147 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
The villa lies in a hilly location with stunning panoramic views of the surrounding hills and mountains, about 8 km from the village of Radicofani. It is an ideal starting point for enjoying the tranquility of the surrounding mountainous landscape and on the other to ma  …see more

from £417 / night

£1667 - £2917 / week

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from £417 / night

(21) Excellent 

1 / 29

San Gimignano / Pancole

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 90 km; Great for children of all ages ; Car essential;
 …see more

from £46 / night

£280 - £405 / week

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from £46 / night

1 / 12

Province of Siena / San Quirico d'Orcia

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £66 / night

£421 - £607 / week

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from £66 / night

(3) Excellent 

1 / 33

Province of Siena / Murlo

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
 …see more

from £67 / night

£459 - £542 / week

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from £67 / night

(32) Excellent 

1 / 24

1 bedroom luxury apartment with Private Garden, Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Car advised;
Surrounded by the famous rolling hills covered with vineyards and olive groves, which give the name to some of the most prestigious Chianti wine is Borgo di Gaiole. The apartment is on the ground floor as you enter the Borgo, private and self contained around 60sq meter  …see more

from £90 / night

£630 - £770 / week

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from £90 / night

(7) Excellent 

1 / 18

3 bedroom farmhouse in the picturesque Tuscan hills boasting private pool, terrace and garden, sleeps 6

Province of Siena / San Gimignano

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Great for children of all ages ;
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £82 / night

£550 - £1042 / week

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from £82 / night

1 / 11

Torrita di Siena flats O - Torrita di Siena apartment sleeps 3

Province of Siena / Torrita di Siena

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Great for children of all ages ; Car advised; No pets allowed;
This beautiful holiday home is located at 200 mt from the pretty medieval village of Torrita di Siena, only 15 km from Pienza and Montepulciano, in the heart of Val di Chiana, an attractive valley in the south-east of the region. The farmhouse faces on a side the villag  …see more

from £60 / night

£200 - £388 / week

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from £60 / night

(28) Excellent 

1 / 20

Amazing Tuscan holiday apartment in the historical Town centre of Colle di Val d'Elsa, sleeps 4

Province of Siena / Colle di Val d'Elsa

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 50 km; Great for children of all ages ; Car advised;
The Dietro Le Mura holiday home has been completely renovated and is located in the historical town centre of Colle di Val d'Elsa, a characteristically medieval town steeped in history. The apartment is on the first floor, has its own entrance and possible parking  …see more

from £67 / night

£450 - £559 / week

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from £67 / night

1 / 48

La Grancia Country Resort Apt4 - Montisi fort sleeps 3

Province of Siena / Montisi

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
La Grancia Country Resort is a romantic and charming 14th century fortress used as a "Grancia", a granary for the storage of the produce grown on the property. Perched next to the delightful hilltop village of Montisi, it overlooks the surrounding Tuscany coun  …see more

from £104 / night

£715 - £794 / week

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from £104 / night

(3) Excellent 

1 / 35

Province of Siena / San Gimignano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Great for children of all ages ;
 …see more

from £84 / night

£525 - £875 / week

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from £84 / night

(6) Very Good 

1 / 18

Holiday apartment in restored Tuscan farmhouse, sleeps 4, features private garden and shared pool

Province of Siena / San Gimignano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
'Podere Torricchi' is a small collection of renovated 16th Century farm buildings converted into luxury houses and apartments. 'Torricchi 6' is a beautiful spacious ground floor house and is located on a hill with stunning views of the Tuscan hills. The renovation has r  …see more

from £75 / night

£525 - £800 / week

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from £75 / night

(6) Excellent 

1 / 10

Province of Siena / Sovicille

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Nearest beach 72 km; Swimming pool; Great for children of all ages ;
 …see more

from £38 / night

£467 - £2100 / week

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from £38 / night

(40) Excellent 

1 / 25

Lovingly restored stone-built Tuscan barn

Province of Siena / San Gimignano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
Podere Torricchi is a small collection of beautifully renovated 16th Century farm buildings converted into houses and apartments. Set on a hill the entire site has stunning views of the rolling Tuscan countryside. I'l Granario' is a house set on two floors, tastefully r  …see more

from £90 / night

£625 - £925 / week

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from £90 / night

(5) Very Good 

1 / 49

La Grancia Country Resort Apt1 - Montisi fort sleeps 3

Province of Siena / Montisi

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
La Grancia Country Resort is a romantic and charming 14th century fortress used as a "Grancia", a granary for the storage of the produce grown on the property. Perched next to the delightful hilltop village of Montisi, it overlooks the surrounding Tuscany coun  …see more

from £104 / night

£715 - £794 / week

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from £104 / night

(3) Excellent 

1 / 25

Province of Siena / Vivo d'Orcia

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 70 km; Ski; Great for children of all ages ;
 …see more

from £59 / night

£375 / week

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from £59 / night

(3) Excellent 

1 / 44

I MELOGRANI I:5 BDR Tuscan villa,view,pool ,WiFi

Province of Siena / San Giovanni d'Asso

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
You could not ask for a more special place in which to celebrate an important anniversary or simply spend a vacation with your family and friends ! I Melograni is a beautiful antique,indipendent, "casale" with large swimming pool (5x12 sqm), 1km away (walking distance!  …see more

from £452 / night

£3167 - £4084 / week

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from £452 / night

1 / 10

STALLINA - Siena apartment sleeps 2

1 bedroomSleeps 22 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Great for children of all ages ; Pets welcome; Private garden;
The apartment is named STALLINA (small barn) and it is a cosy studio apartment forming part of the building of the "SCUDERIA" (stable) with a separate entrance and direct access from the garden. The studio has a living room with sofa bed, kitchenette and bathroom with s  …see more

from £43 / night

£269 / week

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from £43 / night

1 / 13

Province of Siena / Asciano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £110 / night

£631 - £774 / week

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from £110 / night

(7) Very Good 

1 / 24

Delightful holiday house at the edge of Tuscan village of Casciano di Murlo, features private garden, terrace and pool

Murlo / Casciano di Murlo

1 bedroomSleeps 5Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 50 km; Swimming pool; Great for children of all ages ;
Situated at the edge of the village of Casciano di Murlo, about 20 km away from Siena, in the heart of the gorgeous Tuscan countryside. Lovely views over the hills, private veranda with garden furniture and barbecue. Very tranquil location.The house (about 55 square met  …see more

from £55 / night

£359 - £542 / week

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from £55 / night

(4) Excellent 

1 / 23

Pure 5 star Luxury in Tuscany-Jacuzzi-AC-wifi-S

Province of Siena / Pienza

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Great for children of all ages ; Air conditioning; No pets allowed;
New lower price - one of the nicest flat in Tuscany 5 star standard !!The apartment has its own entrance and occupies the whole 1st and top floors of this classical building next to the ancient city wall. Private parking, large roof terrace (55m2) with great views over  …see more

from £117 / night

£0 / week

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from £117 / night

1 / 19

Suite Artista: Cannavacciuolo - Montalcino apartment sleeps 3

Province of Siena / Montalcino

1 bedroomSleeps 32 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Suite d'Artista is a perfect place to enjoy a relaxing holiday combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. Nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming p  …see more

from £121 / night

£0 / week

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from £121 / night

(3) Excellent 

1 / 32

Rustic home Il Torrione, private garden and pool

Province of Siena / Radicondoli

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 50 km; Swimming pool; Great for children of all ages ;
In our rustic house Il Torrione you will find all the peacefulness that only Tuscany can offer the visitor. Our customers will find this large apartment in Radicondoli, town in the green of Tuscany hills, composed by three bedrooms, bathrooms, a kitchen, a living room a  …see more

from £120 / night

£834 - £1042 / week

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from £120 / night

1 / 17

Holiday Resort in Montepulciano M - Montepulciano apartment sleeps 2

Province of Siena / Montepulciano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearest village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists  …see more

from £46 / night

£321 - £671 / week

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from £46 / night

(3) Excellent 

1 / 20

Granaio 7 - San Gimignano apartment sleeps 6

Province of Siena / San Gimignano

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Great for children of all ages ;
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 6 people (4+2) in total. The apartment is next to Granaio nr 6 (nr 277512) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San Gimignan  …see more

from £58 / night

£400 - £875 / week

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from £58 / night

1 / 17

Appartamento Ginestra - Castelnuovo Berardenga apartment sleeps 2

Province of Siena / Castelnuovo Berardenga

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Le Rocche di Valiano is an ancient village situated in the heart of Chianti region near Siena.The structure, completely surrounded by olives groves, enjoys a spectacular view of the typical Tuscany landscape made by sweet hills and of the vast vineyards.The apartment Gi  …see more

from £35 / night

£240 - £490 / week

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from £35 / night

(41) Excellent 

1 / 21

La Casina Toscana, central with parking and wi-fi

Province of Siena / Montepulciano

3 bedroomsSleeps 53 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 158 km; Great for children of all ages ; Car advised;
Placed in the countryside of Montepulciano, near the most important historical towns such as Pienza, Montalcino and Bagno Vignoni, the Casina Toscana is a historical residence of the nineteenth century, which allows guests to enjoy the tranquility and relaxation that th  …see more

from £59 / night

£334 - £584 / week

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from £59 / night

1 / 26

Podere Capanne Rigomagno - Rigomagno house sleeps 6

Sinalunga / Rigomagno

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Part of an old farmhouse set on a hill overlooking the charming medieval village of Rigomagno and a large part of the Chiana Valley. In this area the hills are mostly covered with the silver-green foliage of olive trees, interspersed now and then with a small vineyard o  …see more

from £79 / night

£547 - £1253 / week

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from £79 / night

(2) Excellent 

1 / 22

Balz Tuscan farmholiday Chianti - Radda in Chianti farmhouse sleeps 3

Province of Siena / Radda in Chianti

2 bedroomsSleeps 35 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 120 km; Great for children of all ages ;
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 £57 / night

£350 - £392 / week

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from £57 / night

1 / 25

Appartamento Glicine - Castelnuovo Berardenga apartment sleeps 7

Province of Siena / Castelnuovo Berardenga

2 bedroomsSleeps 7Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Le Rocche di Valiano is an ancient village situated in the heart of Chianti area near Siena. The structure, completely surrounded by olives groves, enjoys a spectacular view of the typical Tuscany landscape made by sweet hills and of the vast vineyards. The apartment  …see more

from £53 / night

£368 - £741 / week

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from £53 / night

(1) Excellent 

1 / 47

Casa Lorenzo: Charming Tuscan house,pool, AC,WiFi

Province of Siena / San Giovanni d'Asso

3 bedroomsSleeps 53 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
Casa Lorenzo is a small indipendent antique house suitable for 5 +1. "what a beautiful charming house you have;we expecially enjoyed the view from the pool ;unparalleded beauty! San Giovanni is a wonderful little town..although we enjoyed all of our day excursion to Mon  …see more

from £200 / night

£1400 - £1950 / week

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from £200 / night

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Casa Degli Olivi Cetona , Siena Tuscany
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What a fantastic experience in the Italian countryside. Two weeks tucked away from tourist mayhem. Even prior to our departure from the Middle East to start our holiday, the owners answered all our enquiries quickly,efficiently with sound advice. The … see more
Tuscan apartment with pool in Cetona
Excellent, centrally located apartment in a charming village

We thoroughly enjoyed our stay in Cetona and, given half a chance, would go back tomorrow! We booked the apartment for two weeks with my husband and I spending the first week on our own, and our two sons and one girlfriend joined us for the second w … see more
Villa Galardini
Great location in heart of Tuscany; wonderful property and very friendly owners

Property is peaceful, clean and ideally located for daytrips to the many nearby villages and Sienna. Grocery stores and restaurants conveniently located in nearby Buonconvento . This was a 50th Birthday celebration vacation to Tuscany with spouse a … see more
I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi
Perfect.

The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arrive on a S … see more

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