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326 Results  |  
24 Photos

Villa | 5 Bedrooms | sleeps 8

7 Nights min stay

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from £457 /night

£3199 - £4653 / 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
Luxury holiday house for 8 persons, with swimming pool , in Chianti  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £49 /night

£343 - £658 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • May take pets – please enquire
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany. Gaiole is in the Chianti Classico area, ideal to taste and enjoy the best wine and food in Italy.  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £180 /night

£1258 - £2353 / 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
Attractive holiday house for 7 persons, with swimming pool , in Siena  …see more

Featured properties

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £353 /night

£2469 - £3379 / 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
Holiday house for 10 persons, with swimming pool , in Montepulciano  …see more

15 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £468 /night

£3270 - £5250 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
Vacation rental Tuscany : This is a large villa in the famous Brunello wine region, located in the midst of a wine estate with some twenty five hectares of surrounding vineyards producing these marvellous wines. In a haven of natural beauty and tranquillity.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £107 /night

£744 - £827 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Leopoldo D is a romantic 60-square-meter (about 646 square feet) apartment which sleeps two people. It features shared swimming pool and garden  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

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from £117 /night

£818 - £1137 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Appartamento Reginaldo A is a pleasant and spacious villa in the characteristic style of the Tuscan countryside. It sleeps six people. From Appartamento Reginaldo A you will enjoy a view of the surrounding countryside and of the towers of San Gimignano  …see more

20 Photos

House | 5 Bedrooms | sleeps 12

1 night min stay

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from £286 /night

£2000 - £2600 / 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
Villa Adalia is an elegant and welcoming apartment that covers the entire top floor of an ancient country manor built on a hillside, surrounded by meadows and woods. It sleeps 12 people. From Villa Adalia you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

Villa | 1 Bedroom | sleeps 2

1 night min stay

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from £75 /night

£521 - £579 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Beata E is a characteristic apartment made of stone. It sleeps two people. From Villa Beata E you will enjoy a pleasant view of the Tuscan countryside  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £633 /night

£4425 - £4950 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
This charming Italian property has been carefully restored by the owner as a fine example of Tuscan rural 18th century style.

 …see more

17 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £125 /night

£872 - £1572 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Apartment for 6 persons, with swimming pool , in San Gimignano  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

7 Nights min stay

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from £366 /night

£2559 - £6139 / 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
Luxury holiday house for 14 persons, with swimming pool , in Pienza - Montalcino  …see more

17 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £72 /night

£499 - £849 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Apartment for 2 persons, with swimming pool , in San Gimignano  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 13

7 Nights min stay

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from £1267 /night

£8868 - £11232 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Villa Margherita is a luxurious villa with infinity pool, set in the hills of Chianti near Siena and Florence. Set atop a hill on two hectares of private gardens with 360-degree views of the Tuscan countryside  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £182 /night

£1270 - £1550 / 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
Casa Emide D is a graceful apartment in a history-rich eighteenth-century estate. It sleeps four people. From Casa Emide D you will enjoy a marvelous view of the greenery. Casa Emide D is 80 square meters (860 square feet)  …see more

20 Photos

Cottage | 2 Bedrooms | sleeps 6

1 night min stay

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from £98 /night

£686 - £984 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Casa Porzia is a gracious cottage of 80 square meters (about 860 square feet) for six people, with garden and access to a pool of 7 X 14 meters (23 X 46 feet)  …see more

8 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £1375 /night

£9625 - £11109 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
villa la corte started as a monastery in the 12th century; until recently long abandoned it has undergone excellent restoration work lasting 4 years, transforming it into a high-quality villa, with modern facilities and services: swimming-pool (15x7 m.), tennis court, private gymnasium with sauna, football field, boules and billiard table. The villa lies in a large estate of over 30 hectacres, and is reached via a private road inside the estate which is partly untarred and partly paved with stones from the riverbed. It lies about 2 kms from ville di corsano, a small village with two restaurants, a bar and a post office. Siena is about 15 kms drive away along a scenic road. The whole of chianti is a leisuredly visit - san gimignano and monteriggioni are easy to reach, and further south, the val d'orcia, montalcino, montepulciano, pienza all make interesting cultural and gastronomic trips. Firenze is less than an hour and a half by car. The large garden surrounding the villa is beautifully looked after and in the summer months there is an explosion of colourful flowers with the centuries-old trees towering above. For the furnishings they have installed very high-quality antiques, and there is also the following equipment: an external kitchen with fridge close to the swimming-pool, central heating, telephone, fax, internet connection, private laundry. The staff can prepare meals for you, offering menus of excellent tuscan cuisine. The scenery around the villa is wonderful, and the beauty of the well-known "crete senesi" changes colour according to the season. Air-conditioning in the bedrooms (all with hastens beds).  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £71 /night

£492 - £703 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Monia D is a welcoming cottage made of stone. It sleeps four people. From Casa Monia D you will have a pleasant view of the Tuscan hills. Casa Monia D is 50 square meters (540 square feet)  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £353 /night

£2470 - £3250 / 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
Villa Calpurnia is a charming two-story historical villa situated in the heart of the Tuscan countryside. It sleeps eight people. From Villa Calpurnia you will enjoy a spellbinding view of the Chianti hills and of the vineyards  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

7 Nights min stay

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from £47 /night

£327 - £600 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany. Gaiole is in the Chianti Classico area, ideal to taste and enjoy the best wines and olive oil in Italy.  …see more

20 Photos

Villa | 18 Bedrooms | sleeps 35

7 Nights min stay

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from £5260 /night

£36815 - £47595 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
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

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £86 /night

£596 - £794 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Sole is an apartment of 50 square meters (about 538 square feet), for four people. It is part of an historic stone house, and has a patio, it also shares a pool and a 4000 square meter (about 1 acre) park  …see more

11 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £257 /night

£1795 - £2510 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
Italian village rental - This charming historical residence is part of a larger building, located in the village of San Giovanni d'Asso, just beyond the original castle walls and a short walk to the centre. 
 …see more

9 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £106 /night

£739 - £1683 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Holiday house for 4 persons, with swimming pool , in San Gimignano  …see more

24 Photos

Villa | 1 Bedroom | sleeps 2

7 Nights min stay

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from £82 /night

£568 - £803 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Holiday house for 2 persons, with swimming pool , in San Gimignano  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £97 /night

£677 - £1193 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Apartment for 4 persons, with swimming pool , in San Gimignano  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £68 /night

£476 - £934 / week

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Key info:

  • Nearest beach 72 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
This charming farmhouse complex is the result of a recent and elegant restoration of a typical Tuscan country complex, near the town of Casole d'Elsa, in the province of Siena.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 18

7 Nights min stay

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from £879 /night

£6149 - £7686 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Its independent location surveys a luminous valley in the heart of Tuscany, where you will have the chance to enjoy the beauty of a new discovered nature also through the taste of its cuisine.  …see more

16 Photos

Villa | 9 Bedrooms | sleeps 18

2 Nights min stay

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from £1179 /night

£8250 - £16250 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annex. It is surrounded by breathtaking views over the Italian countryside  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £533 /night

£3725 - £4967 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This villa is an elegant 18th century mansion near Siena in the Chianti wine region, perfect for visiting Tuscany and relaxing by the pool during your holidays in Italy. The villa has a vantage position on a hill above the old town of Staggia Senese. From the ...  …see more

8 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £274 /night

£1912 - £2813 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
fine villa situated in the hills of the chianti classico area just a short distance from poggibonsi, just 3 kms away, where guests can find shops of all kinds. All the most famous place in chianti are within easy reach of the villa, such as castellina in chianti, radda and greve, as well as san gimignano with its famous towers, and the art cities of florence and siena are just half an hour away by car. The villa is set in a splendid position, peaceful and panoramic. It is beautifully furnished with quality pieces, and equipped with dishwasher, washing machine and satellite tv, wifi internet connection and air-conditioning  in all the rooms. Guests also have at their disposal a spacious, fully-equipped garden, complete with a 5x10 m swimming pool and a barbecue. Private car park and garage within the property. There are numerous restaurants nearby where guests can savour the famous tuscan cuisine and wine.  …see more

20 Photos

House | 6 Bedrooms | sleeps 12

1 night min stay

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from £600 /night

£4200 - £5600 / 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
Villa Cherubina is a splendid sixteenth-century three-story villa located on top of a small hill. It sleeps 12 people. From Villa Cherubina you will enjoy a wonderful view of the Senesi hills. Villa Cherubina is 500 square meters (5380 square feet)  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 18

2 Nights min stay

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from £1179 /night

£8250 - £16250 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
The exquisite villa is located in Contignano surrounded by spectacular views of rolling clay hills and countryside. The villa sleeps up to 19 in 8 very spacious bedrooms, 2 twins, 5 doubles and a lofted bedroom containing a sofa bed, a twin and a double bed  …see more

16 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £48 /night

£336 - £475 / 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
Apartment for 4 persons, with swimming pool , in Siena  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £167 /night

£1165 - £1744 / 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
Holiday house for 6 persons, with swimming pool , in Chianti  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 6

1 night min stay

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from £65 /night

£455 - £868 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Villa Davide F is an elegant apartment surrounded by the vegetation. It sleeps six people. From Villa Davide F you will enjoy a pleasant view of the Tuscan countryside. Villa Davide F is 80 square meters (860 square feet)  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £355 /night

£2480 - £3720 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Eracle is a bright and elegant three-story villa surrounded by vineyards and olive groves. It sleeps eight people. From Villa Eracle you will enjoy a fascinating view of the Chianti hills and of the vineyards  …see more

13 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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from £322 /night

£2250 / 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
Villa on Private vineyard with swimming pool. Incredible views of the picturesque Tuscan countryside  …see more

8 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £2117 /night

£14814 - £16050 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
villa la corte started as a monastery in the 12th century; until recently long abandoned it has undergone excellent restoration work lasting 4 years, transforming it into a high-quality villa, with modern facilities and services: swimming-pool (15x7 m.), tennis court, private gymnasium with sauna, football field, boules and billiard table. The villa lies in a large estate of over 30 hectacres, and is reached via a private road inside the estate which is partly untarred and partly paved with stones from the riverbed. It lies about 2 kms from ville di corsano, a small village with two restaurants, a bar and a post office. Siena is about 15 kms drive away along a scenic road. The whole of chianti is a leisuredly visit - san gimignano and monteriggioni are easy to reach, and further south, the val d'orcia, montalcino, montepulciano, pienza all make interesting cultural and gastronomic trips. Firenze is less than an hour and a half by car. The large garden surrounding the villa is beautifully looked after and in the summer months there is an explosion of colourful flowers with the centuries-old trees towering above. For the furnishings they have installed very high-quality antiques, and there is also the following equipment: an external kitchen with fridge close to the swimming-pool, central heating, telephone, fax, internet connection, private laundry. The staff can prepare meals for you, offering menus of excellent tuscan cuisine. The scenery around the villa is wonderful, and the beauty of the well-known "crete senesi" changes colour according to the season. Air-conditioning in the bedrooms (all with hastens beds).  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

rentals_reviews_rating_1 

1 night min stay

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from £78 /night

£546 - £769 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Casa Polliana is a gracious cottage of 60 square meters (about 645 square feet) for four people, with garden and access to a pool of 7 X 14 meters (23 X 46 feet)  …see more

16 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £1558 /night

£10900 - £15180 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
Large air conditioned villa near Siena - Villa Santa Caterina is an imposing fully restored 13th-century monastery, subsequently used as a farmhouse, which has been transformed into an elegant country holiday house.  …see more

24 Photos

Villa | 11 Bedrooms | sleeps 22

7 Nights min stay

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from £677 /night

£4734 - £6667 / 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
Luxury holiday house for 22 persons, with swimming pool , in Siena  …see more

16 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £707 /night

£4943 - £8695 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
La Maccinaia is a beautiful property located in a very quiet location, in the heart of the Chianti region, between Gaiole and Castelnuovo Berardenga. The main villa dates to the 17th century, and has been immaculately restored by its Belgian owner who combined modern  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £524 /night

£3662 - £6505 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
This Italian vacation rentals Villa has its independent location surveys a luminous valley in the heart of Tuscany, where you will have the chance to enjoy the beauty of a new discovered nature also through the taste of its wine and Italian cuisine  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £180 /night

£1260 - £1450 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Appartamento Cecco C is an elegant and welcoming apartment. It sleeps six people. It is appoximately 90 square meters (970 square feet)  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 5

1 night min stay

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from £114 /night

£796 - £1092 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Appartamento Reginaldo G is a charming villa in the characteristic style of the Tuscan countryside. It sleeps five people. From Appartamento Reginaldo G you will enjoy an enchanting view of the surrounding countryside and of the towers of San Gimignano  …see more

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House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £525 /night

£3675 - £5938 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
This beautifully restored 14th century farmhouse sits within a farming estate on a hilltop with magnificent views over the soft hills of the Arbia river valley.  …see more

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Farmhouse | 6 Bedrooms | sleeps 16

7 Nights min stay

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from £551 /night

£3852 - £6439 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This exceptionally beautiful property is located in a very quiet and spectacular position, just a few kilometres away from the lovely village of Montalcino. The views from the house are outstanding taking in the Val d'Orcia and Crete Senesi  …see more

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Villa | 12 Bedrooms | sleeps 24

7 Nights min stay

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from £2232 /night

£15620 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
The villa is elegant and majestic in its eighteenth century form, the location is stunning with excellent furnishing and a beautiful garden, a welcoming and cozy atmosphere in a perfect Italian style Villa.  …see more

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Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £980 /night

£6860 - £7604 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Relais Chianti is a typical Tuscan homestead from the early 1800s located in the unmistakable Chianti Classico countryside, in the renowned vine-growing and wine-making region.  …see more