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124 Holiday homes in Siena Province

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124 Results  |  
11 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £51 /night

£356 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Immerso nella meravigliosa campagna toscana LA DOLCE VITA è un affittacamere all'interno di un antico casolare ristrutturato, circondato dall'atmosfera magica della natura incontaminata.  …see more

20 Photos

House | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £41 /night

£281 - £456 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Sun in summer, snow in winter, hiking, culture and charm of nature nothing is missing for a wonderful holiday in the comfortable house Contignano. The price is guaranteed. There are no additional charges. Utilities are included in the price.  …see more

19 Photos

House | 15 Bedrooms | sleeps 30

Min stay varies

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
Poggiarello is a special place to spend a charming holiday in close contact with nature, where is possible to reach in few minutes Siena, San Gimignano, Firenze, Pisa, Lucca, Monteriggioni,Montalcino.  …see more

Featured properties

13 Photos

House | 5 Bedrooms | sleeps 14

Very Good 4/5 

Short stays welcome

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from £83 /night

£575 - £1236 / week

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Late Deal: save up to €372 (approx. £307)

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Located on a hill overlooking the Val D'Orcia Tuscany's only Unesco heritage site is truly beautiful. A stay here will relax body and mind. We now offer excellent home cooked food within your house in the traditional tuscan style and cater for large or small groups.  …see more

17 Photos

House | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £87 /night

£605 - £894 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Belsedere is located on the top of a hill, near Pienza, Montepulciano, Cortona, Monte Oliveto Maggiore, Siena. There are four apartments, which overlook the garden of the villa or the grove of oaks beside the pool. Breakfast included. During the high season we offer a Sunday evening dinner guests of the farm.  …see more

14 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £82 /night

£570 - £701 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Typical house in the heart of Siena's countryside,suitable for vacations from Spring to late October; come and discover the true pleasure of a vacation in Tuscany -150 euro damage deposit to be paid cash upon arrival -Internet conn. on request 6€ per 3GB or 20€ for 10GB  …see more

11 Photos

House | 2 Bedrooms | sleeps 7

3 Nights min stay

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from £62 /night

£430 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Extraordinary typical tuscan historic eighteenth-century residence, all restored, all high standard confort, located on a hilltop in the Siena countryside, in the charming medieval village Sinalunga. You will love your holidays there! Come and live the tuscan way of life : relaxing, friendly, refined.  …see more

8 Photos

House | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £296 /night

£2067 - £2728 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • May take pets – please enquire
If you are searching for something very special, with charm, history and love for details- thats the place to be. It it the perfect hub to discover the jewels of tuscany (if you want to stay in lovely apartments with your friends) or to celebrate a ferry tale wedding-  …see more

10 Photos

House | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £142 /night

£992 - £1323 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Make Stomemmano the destination, not just the base for your Tuscan holiday!  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £56 /night

£386 - £877 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
The accommodation is very comfortable and well equipped.There are several tables and chairs outside where one can enjoy a meal and glass of wine watching the stunning view until darkness falls then watching the fireflies float around as you appreciate the calm serenity  …see more

24 Photos

House | 13 Bedrooms | sleeps 36

Very Good 4/5 

2 Nights min stay

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from £472 /night

£3300 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
On the sweet hills of the Chianti shire between vineyardand and olive groves, stands the "Podere il Pino". It offers a spectacular view on the beautiful medieval village of San Gimignano and it is very close to art cities as Florence, Siena, Pisa, Volterra and the sea.  …see more

20 Photos

House | 6 Bedrooms | sleeps 16

Min stay varies

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from £551 /night

£3852 - £6439 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Elegant country décor. Airy and spacious rooms. Air conditioning in the first floor bedrooms. Optional guest house.  …see more

20 Photos

House | 6 Bedrooms | sleeps 12

Min stay varies

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from £390 /night

£2728 - £5372 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Peaceful position for a holiday of total relax in Chianti. Fenced pool. Very panoramic outdoor eating area. Tennis court on the estate.  …see more

20 Photos

House | 4 Bedrooms | sleeps 8

Min stay varies

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from £294 /night

£2058 - £3290 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Once a watermill. Original architecture and contemporary design. Close to San Gimignano.  …see more

15 Photos

House | 3 Bedrooms | sleeps 6

Min stay varies

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from £284 /night

£1984 - £3224 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Located in the Volpaia hamlet (Chianti region) with local restaurant. Private and panoramic position. Tennis court on the estate.  …see more

10 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £91 /night

£636 / week

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Key info:

  • Nearest beach 50 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This house is set in a very convenient location for touring the cities of Tuscany. Siena, Florence and Pisa are all easily accessible by car or public transport.  …see more

20 Photos

House | 4 Bedrooms | sleeps 5

Very Good 4/5 

7 Nights min stay

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from £89 /night

£622 - £1288 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
CASALTA di PESA: Beautiful stone Tuscan hamlet in the splendid Chianti Classico vineyards. This property still shows the blazon of the astronomer Galileo Galilei who stayed in this hamlet many years and drew inspiration from the beauties of the surrounding landscape. Casalta di Pesa is an Holiday Home surrounded by vineyards, just outside Castellina in Chianti  …see more

24 Photos

House | 1 Bedroom | sleeps 5

Very Good 4/5 

3 Nights min stay

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from £50 /night

£348 - £538 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Tuscany, near Siena. Lovely small villa in the beautiful countryside, with large garden, veranda and private pool. Ideal for a relaxing holiday in full nature as well as for interesting visits to the sites of art in the area. The house is really cosy, situated in a very central and tranquil location. Siena is only 20 min. drive.  …see more

9 Photos

House | 2 Bedrooms | sleeps 4

Min stay varies

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from £95 /night

£662 - £992 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
3-room house 90 m2, on the ground floor, very tasteful furnishings: 1 room with 2 beds. 1 double bedroom with with corner bath.  …see more

10 Photos

House | 1 Bedroom | sleeps 3

Short stays welcome

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from £53 /night

£371 - £446 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Tuscany, self catering, holiday let, Italy, romantic holiday, honey moon, casale  …see more

14 Photos

House | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £83 /night

£575 - £1153 / week

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Late Deal: save up to €372 (approx. £307)

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
This is a beautiful traditional stone house completely refurbished over two years ago. As a result the fit out is of a very high quality.Located on a hill overlooking a Unesco world heritage site with wonduferfu; views and sunsets to take home.  …see more

13 Photos

House | 3 Bedrooms | sleeps 8

Short stays welcome

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from £118 /night

£823 - £1484 / week

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Late Deal: save up to €750 (approx. £620)

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Beautiful Three bedroom stone house spread over three floors with the master bedroom on the top floor entered by a spiral staricase. Fully fitted kitchen with fridge freezr, dishwasher, oven and hob with all of the cooking equipment supplied.  …see more

15 Photos

House | 1 Bedroom | sleeps 3

1 night min stay

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from £44 /night

£307 - £587 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
The apartment is located just 5 minutes drive from the walls surrounding the old town (10 min by bus) and its location also allows you to quickly reach the surroundings of the Sienese countryside. Supermarket and shops nearby. Being a one bedroom apartment of about 45 square meters, is ideal for 2 people, maximum of 3.  …see more

20 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £141 /night

£982 - £1840 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Self-catering holiday house in the heart of Tuscany, private swimming pool, quiet place with stunning panoramic view . Holiday house is ideal for families, groups seeking relaxation, romantic gateway. No smoking vacation house, near Siena. Pet friendly rentals. Dream holiday with private swimming pool and garden, quiet area with beutiful views of the Tuscan country  …see more

16 Photos

House | 2 Bedrooms | sleeps 6

Short stays welcome

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from £83 /night

£575 - £1153 / week

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Late Deal: save up to €372 (approx. £307)

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Beautiful newly restored two bedroom house with large kitchen, living room, garden and a swimming pool. Incredible unbroken 360 views over the Val D'Orcia valley. Sun-baked stone walls hand made terracotta floors, chestnut beams, pergolas twisted with wisteria. Located in the Val d'Orcia region south of Siena.  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

5 Nights min stay

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from £83 /night

£575 - £880 / week

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Key info:

  • Nearest beach 55 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautifully restored 16th century Granary building; stunning views of the Tuscan hills. Perfect for a romantic holiday; explore the best Tuscany has to offer or a family getaway. Gorgeous pool area and large private garden. Easy access to Florence, Pisa and Siena. The house has been tastefully renovated and is equipped to a very high standard throughout.  …see more

19 Photos

House | 1 Bedroom | sleeps 4

Short stays welcome

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from £38 /night

£263 - £439 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The apartment is situated in a residence which rapresent the perfect tuscan style. Centuries ago it was a convent, then it was inhabitated by farmers. It's the perfect place where you can spend your holidays in tranquility and relax, inside the typical Tuscan country.  …see more

17 Photos

House | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £57 /night

£395 - £439 / week

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Key info:

  • Not suitable for children
  • Car advised
  • May take pets – please enquire
Opportunity awaits you to experience your Italian holiday in this unique home. The history and character of the home, neighborhood and Cetona will make you feel immersed in the lifestyle and truly feel like a local. A short stroll from the home will take you to the piazza where you find restaurants, cafes, and shops.  …see more

17 Photos

House | 2 Bedrooms | sleeps 3

Excellent 5/5 

7 Nights min stay

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from £69 /night

£482 / week

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Key info:

  • Nearest beach 95 km
  • Suitable for over 5s only
  • Car not necessary
  • Pets welcome
Il palio di Siena, Firenze, Lucca, Val d'Orcia, Montalcino, Pienza, Bagno Vignoni, Montepulciano Private parking and bus stop for the center right in front of the villa!  …see more

14 Photos

House | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £418 /night

£2920 - £3963 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Walk to the local restaurants & grocery store or drive a short distance to numerous historical towns, but still enjoy the privacy & beautiful scenery of Tuscany. Dine 'al-fresco' under the vine-draped pergola & swim in the pool that looks out upon a timeless landscape. If you desire privacy with convenience; scenic views without isolation, Casa Oliveto is for you!  …see more

21 Photos

House | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £120 /night

£840 - £1440 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Casa Sale is an independent stone house surrounded by a garden with olive trees, located in a small hamlet, just 4km outside Sovicille, about 10km from Siena.  …see more

24 Photos

House | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £83 /night

£579 - £1240 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Charming Tuscany villa with private pool & garden. Ideal for families  …see more

19 Photos

House | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £166 /night

£1157 - £1836 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjoy!  …see more

22 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £126 /night

£877 - £1315 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Podere campana is a small organic farm located on a delightful hill surrounded by olive groves and vineyards, iPodere campana is a small organic farm located on a delightful hill surrounded by olive groves and vineyards, in the heart of the Valdichiana senese.  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £84 /night

£587 - £877 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Podere campana (www.poderecampana.it) is a small organic farm located on a delightful hill surrounded by olive groves and vineyards, in the heart of the Valdichiana senese.  …see more

24 Photos

House | 5 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £188 /night

£1315 - £1972 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
- In Valdichiana senese only a few kilometres from: Pienza,Montepulciano,Montalcino,Cortona,Siena, Arezzo and Perugia. - holidays in unique countryside, ancient cities, exquisite works of art and delicious food! - swming pool only for your exclusive use  …see more

24 Photos

House | 1 Bedroom | sleeps 3

Min stay varies

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from £51 /night

£351 - £701 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to enjoy the calm, the beauty and all the pleasures our region has to offer. Our apartments have been renovated with respect for tradition.  …see more

13 Photos

House | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £101 /night

£701 - £1052 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Very confortable countryhouse, in the heart of Chianti hills, ideal for family or groups who wants to visit the best of Tuscany and relax in the country. Four large bedrooms, two bathrooms, large livingroom with fireplace, kitchen, big garden, internet wifi.  …see more

24 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £294 /night

£2058 - £3290 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
About our villas in italy This lovely property is located only 5 Kms from the centre of San Gimignano, famous for its beautiful towers. This is the place for those who look for piece and quiet, who like nature, gardens, birds.  …see more

22 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £284 /night

£1984 - £2397 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
La Commenda is located in a quiet and secluded position in the Volpaia hamlet. This small, rural hamlet with its fortified walls dating from Medieval times, is one of the best remaining examples of its kind in Tuscany. It is located, just north of Radda in Chianti  …see more

22 Photos

House | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £354 /night

£2472 - £4951 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
This property is located in the fortified medieval hamlet of Volpaia, in the Chianti Classico area, in a secluded position ensuring complete privacy. It is just a 300 metre walk to the centre of the hamlet, with two restaurants, one of which managed by the Castello  …see more

16 Photos

House | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £505 /night

£3529 - £5182 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Il Colombaio is a peaceful oasis in the heart of Chianti Classico, with expansive views on rolling hills and rows of vineyards. The location, near the village of Gaiole in Chianti, is perfect for visiting the several hilltop villages such as Radda, Castellina and Greve  …see more

14 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £354 /night

£2472 - £3554 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
This very special property is located on the edge of Castello di San Donato in Perano (Chianti), a beautiful hamlet which has recently been restored to such a high standard that it was awarded by the International Property Awards 2006.  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £122 /night

£850 - £1220 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villino Gelia is a splendid two-story age-old farm house surrounded by meadows and by green hills. It sleeps six people. From Villino Gelia you will enjoy a breathtaking view of the Senesi hills and of the greenery. Villino Gelia is 90 square meters (970 square feet)  …see more

20 Photos

House | 1 Bedroom | sleeps 4

1 night min stay

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from £56 /night

£389 - £629 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria B is a gracious 100-square-meter (about 1076 square feet) house on a hill which sleeps four people. It features a private hill and shared garden and swimming pool  …see more

20 Photos

House | 3 Bedrooms | sleeps 8

1 night min stay

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from £93 /night

£645 - £1009 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria E is a 100-square-meter (1076 square feet) house on a hill which sleeps eight people. It features a private patio and shared garden and swimming-pool. It is part of a small medieval hamlet consisting of stone houses restored as vacation homes  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £82 /night

£571 - £1116 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Giobatta I is a 120 square meter (approximately 1290 square feet) house in the countryside for four people, with a private garden, and shared swimming pool, tennis court and garden  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £129 /night

£900 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Diora C is a characteristic and welcoming apartment that is part of a villa surrounded by vineyards and olive groves. It sleeps four people. From Villa Diora C you will enjoy an enchanting view of the Tuscan hills and of the Chianti valley  …see more

16 Photos

House | 6 Bedrooms | sleeps 14

7 Nights min stay

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from £1169 /night

£8182 - £12810 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Located on a wine producing estate, this magnificent property has a 360 degree view on the surrounding countryside, close to the village of Casole d'Elsa. Decorated with exceptional taste and attention to detail, it has been completely restored in the last few years and  …see more

20 Photos

House | 1 Bedroom | sleeps 4

1 night min stay

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from £56 /night

£389 - £629 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria L is a gracious 40-square-meter (about 430.5 square feet) house on a hill which sleeps four people. It features a garden and a shared swimming-pool. It is part of a small medieval hamlet consisting of stone houses restored as vacation homes  …see more