Cycling holiday villas and apartments Province of Siena | Holiday Lettings

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1,012 Holiday homes

Filters applied: Cycling holidays (1,012)

(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 £85 / night

£463 - £715 / week

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from £85 / 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

(6) Excellent 

1 / 24

Province of Siena / San Gimignano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 70 km; Great for children of all ages ; Car advised;
 …see more

from £93 / night

£589 - £706 / week

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from £93 / 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 £152 / night

£883 - £1261 / week

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from £152 / night

(40) Excellent 

1 / 19

Stunning farmhouse apartment located between Tuscan cities of San Gimignano and Volterra, shared pool, private garden, sleeps 6

Province of Siena / San Gimignano

3 bedroomsSleeps 64 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Car essential;
Azzurra is an apartment in Poderra Torrichi, a gated community of three farm buildings, which is located between the medieval cities of San Gimignano and Volterra. Podera Torrichi is newly renovated and has retained the charm of the traditional Tuscan farm buildings, wi  …see more

from £184 / night

£993 - £1451 / week

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from £184 / 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

(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 £85 / night

£463 - £715 / week

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from £85 / 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 £68 / night

£387 - £1732 / week

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from £68 / 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 £83 / night

£555 - £1051 / week

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from £83 / night

1 / 19

Casa Oliveto - Monteguidi apartment sleeps 4

Casole d'Elsa / Monteguidi

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 72 km; Swimming pool; Great for children of all ages ;
The tastefully decorated and comfortably furnished measures about 62 square metres, is located on the ground floor with independent entrance and private garden, and it is composed of 2 large double bedrooms, 2 bathrooms with shower, a full kitchen and a living room.It  …see more

from £86 / night

£597 - £975 / week

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from £86 / 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

£379 / week

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from £59 / 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

1 / 18

Fattoria il Musarone - La Tramontana. Sinalunga

Province of Siena / Sinalunga

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
In the heart of the countryside only 40 minutes from Siena five beautiful apartments have been made by restoring an old Tuscan country house set on a hillside with views all around. Each apartment retains its fascinating original characteristics. A courtyard around the  …see more

from £86 / night

£597 - £1051 / week

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from £86 / night

(1) Excellent 

1 / 12

Sienahomeandsailing-Green apartment - Siena apartment sleeps 4

Province of Siena / Siena

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
Green apartment is located at ground floor and easily accessible, perfect for a family. It consists of a fully equipped kitchen where a folding sofa bed for two guests is provided, a bedroom with a double bed, a bathroom with shower, toilet, hairdryer, washing machin  …see more

from £37 / night

£0 / week

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from £37 / night

(1) Excellent 

1 / 17

Tuscan hillside farmhouse with private pool, terrace and garden, great for family holidays

Province of Siena / San Gimignano

2 bedroomsSleeps 6Min stay varies

  • 2 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 £62 / night

£416 - £925 / week

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from £62 / 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 £68 / night

£454 - £564 / week

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from £68 / 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 £106 / night

£0 / week

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from £106 / 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

£471 - £2118 / week

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from £38 / 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 £47 / night

£282 - £408 / week

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from £47 / night

(54) Excellent 

1 / 52

Incredible, large Tuscan villa boasts jacuzzi, private outdoor pool, billiard room, tennis court, tripadvisor Certificate of Excellence

Province of Siena / Sinalunga

12 bedroomsSleeps 26Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
Key info: Nearest beach 170 km; Swimming pool; Great for children of all ages ;
Villa Scopetello is the perfect holiday home for large groups and families who wish to spend their holidays together. (Between September and May it is also possible to rent just a portion of the Villa or even one bedroom) The 1000 square meter large Villa with 12 bedro  …see more

from £334 / night

£2337 - £7564 / week

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from £334 / 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 £85 / night

£463 - £715 / week

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from £85 / 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 £421 / night

£1681 - £2942 / week

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from £421 / 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

£362 - £547 / week

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from £55 / 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 £105 / night

£721 - £800 / week

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from £105 / 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 £48 / night

£295 - £379 / week

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from £48 / night

1 / 17

Province of Siena / Siena

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 83 km; Swimming pool; Great for children of all ages ;
 …see more

from £80 / night

£412 - £723 / week

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from £80 / 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

(4) Excellent 

1 / 16

Pornano - Radda in Chianti apartment sleeps 3

Province of Siena / Radda in Chianti

1 bedroomSleeps 34 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 4 nights min stay
Key info: Great for children of all ages ; Car essential; Some pets are welcome - please contact the owner;
The accommodation comprises of one double bedded bedroom with en suite bathroom and very well equipped living room/kitchen area looking out onto a pleasant flowery courtyard. Ideal for a couple seeking peace and solitude and it is centrally located to visit Florence, Si  …see more

from £50 / night

£350 - £400 / week

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from £50 / 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 £105 / night

£721 - £800 / week

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from £105 / night

(4) Very Good 

1 / 43

Chianti house, Florence, Siena, Jacuzzi, Tuscany

Gaiole in Chianti / Montefienali

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and na  …see more

from £46 / night

£263 - £505 / week

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from £46 / 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 £118 / night

£0 / week

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from £118 / night

1 / 13

Piccolo Cottage San Gimignano - San Gimignano cottage sleeps 4

Province of Siena / San Gimignano

1 bedroomSleeps 44 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay
Key info: Great for children of all ages ; Pets welcome; Private garden;
Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in modern-style using and bright terracotta floors, the airy home contains 1 double bedroom.  …see more

from £40 / night

£0 / week

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from £40 / 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

(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

£337 - £589 / week

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from £59 / night

(6) Excellent 

1 / 26

Just 5 minutes from the centre of the Gaiolie, wonderful apartment with pool and breathtaking terrace, sleeps 6

Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
The apartment is just 5 minutes walk from the center of Gaiole, where you will find all the services you need. Like restaurants, bars, wineshops, banks, food shop, hairdressers etc.Gaiole is one of several traditional Chianti villages in the region. Others worth visitin  …see more

from £83 / night

£580 - £921 / week

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from £83 / 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 £97 / night

£601 - £795 / week

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from £97 / night

(1) Excellent 

1 / 22

Granaio 6 - San Gimignano apartment sleeps 7

Province of Siena / San Gimignano

2 bedroomsSleeps 7Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
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 7 (5+2) people in total. The apartment is next to Granaio nr 7 (advert nr 277234 ) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San  …see more

from £84 / night

£412 - £908 / week

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from £84 / night

(5) Excellent 

1 / 26

Impressive stone-built cottage with private grounds and pool close to medieval Tuscan town of Colle Val d'Elsa

Province of Siena / Colle di Val d'Elsa

3 bedroomsSleeps 57 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Nearest beach 65 km; Swimming pool; Great for children of all ages ;
This interesting and beautiful stone-built house is peacefully located in the country side just 1 km way from the mediaeval town of Colle Val d'Elsa. Casavico is the result of a recent renovation which has transformed this ancient barn (once belonging to the nearby  …see more

from £73 / night

£505 - £1345 / week

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from £73 / night

(1) Excellent 

1 / 16

Classic Tuscan farmhouse on a hilltop with brilliant views of the countryside, outdoor pool

Province of Siena / San Gimignano

7 bedroomsSleeps 131 night min stay

  • 7 bedrooms
  • Sleeps 13
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
Torreprima holidays house is 3 Km away from the historical center of San Gimignano, and is situated on top of a hill from where it is possible to delight the beautiful view over the surrounding valleys of olive groves and vineyards. It has availability of 5 apartments.  …see more

from £118 / night

£522 / week

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from £118 / night

1 / 20

Province of Siena / Siena

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Suitable for children age 5+; Car advised; Some pets are welcome - please contact the owner;
 …see more

from £64 / night

£442 / week

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from £64 / night

Top Destination reviews

Villa PetrAlexa, Tuscany cottage in Chianti area
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 perfectly prepared. The house was heated up and foo … see more
The Beautiful Sun Apartment
Well maintained apartment and very helpful owner

Elias iwas most helpful meeting us on arrival and going through everything with us and all places to visit in the area even giving us a map with this all marked on The apartment is beautifully kept and everything we needed was there. All to a good s … see more
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
Il Giardino
lovely and peaceful

Il Giardino is a wonderful, intimate place. The house is not huge - but it is perfect for a family.The outside space is so beautiful and serene - the pool and gardens and hammocks and olive groves and flowers and herbs.... We loved, too, that it is … see more
Villa Vianci
Best vacation ever!

Our entire experience at Villa Vianci was beyond expectations. We travelled with 4 generations, ages 3 1/2 to 85! The villa was spectacular, spacious & immaculate. The pictures on line don't do it justice. Tommasso & Chiara were the best, any que … see more
Farm holidays in Chianti
A Christams dream

This year my husband and I decided to spend Christmas on our own, in the Chianti countryside. La Capanna delle Cozzole is just the perfect location: very quiet, romantic and private location. In the village you can find top quality food, wine and d … see more

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