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41 Holiday homes in Siena

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41 Results  |  
22 Photos

Villa | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £188 /night

£1315 - £1840 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Traditional Farmhouse / Villa In Siena (Tuscany) with stunning views. A place to create memories.  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £106 /night

£736 - £1358 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Holiday Villa for 8 people 1 km from Siena, and 3.5 km from Piazza del Campo (sit of the Palio)  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 7

Very Good 4/5 

3 Nights min stay

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from £84 /night

£587 - £1017 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Gorgeous holiday villa in Siena, just 5 minutes walking from the town. blloming garden, shared swimming pool, private car parking, internet (with flash drive), laundry room, chef for dinner or meal on request  …see more

Featured properties

20 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

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from £226 /night

£1577 - £2979 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
This beautiful villa in Siena is situated on the hills with a breathtaking view over the vineyards up to Siena. An ideal accommodation for all those seeking peace and quiet but also a perfect point of departure for visiting the beautiful attractions of the Chianti  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 7

6 Nights min stay

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from £148 /night

£1034 - £2164 / week

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Late Deal: save up to €746 (approx. £617)

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
Charming Chianti villa, Siena 6 km far away, with different prices from 4 to 7 persons, fantastic pool (12x6 meters), terrace with pergola and stunning view on the countryside. Ideal position to visit the most important towns of the Chianti and Val d'Orcia areas, like Castellina in Ch  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £142 /night

£992 - £1612 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Immersed in the green countryside on the outskirts of Siena, Villa Palio offers all the quiet of its natural setting just a stone throw from the very center of the town of Siena.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £178 /night

£1240 - £1984 / 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
A cypress tree lined road will lead you to Villino le Tortore and it represents a perfect introduction to this amazing Tuscany villa located just 15 minutes walking from Piazza del Campo, the very heart of Siena.  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £107 /night

£744 - £2058 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Villa Le Tolfe is so close to Siena you can almost touch it (only 3 kilometres away). With stunning views and beautiful antique gardens this villa is perfect for relaxed stress free holidays.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £355 /night

£2480 - £3265 / 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
Villa Nuti is an elegant XVII century manor only 3 km from the center of Siena. From its unique terrace it enjoys privileged magnificent views of the town with its famous bell towers.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £185 /night

£1290 - £2281 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious detached villa in hilly and quiet location with a beautiful panorama in southern Tuscany. Pool, Jacuzzi (all for private use of the tenant).  …see more

21 Photos

Villa | 9 Bedrooms | sleeps 21

7 Nights min stay

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from £414 /night

£2893 - £4050 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Detached villa with private pool 35 km eastern of Siena. It is an expansive property providing a high standard of accommodation. Tasteful furnished. Hilly and quiet location. The whole property is for private use of the tenant. 9 bedrooms, 17+4 sleeps. Billiard room.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

1 night min stay

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from £172 /night

£1200 - £1950 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Perfectly located just a short walk from the centre of Siena and easily accessible from the train station, this 5 bedroom villa has been beautifully furnished in a modern, contemporary, minimalist style. Surrounded by parkland, guests enjoy use of a salt water swimming pool. WIFI. BBQ. Walking distance to restaurants.  …see more

19 Photos

Villa | 1 Bedroom | sleeps 4

2 Nights min stay

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from £53 /night

£371 - £689 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Villa Malamerenda vacation house is located among the beautiful Sienese hills with breathtaking views and just a short distance from Chianti, offers its guests extremely elegant apartments.Private Pool.Ideal for people who seeking relaxation. The city center is just a short drive away where you can enjoy the Piazza del Campo and Duomo  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £857 /night

£5995 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Spectacular 5 bedroom villa with private pool in a beautiful Tuscany setting just 14kms from Siena. The property is serviced and guests receive a complementary meal on arrival.  …see more

11 Photos

Villa | 3 Bedrooms | sleeps 8

Min stay varies

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Charming, renovated country villa rental with pool, situated in the countryside, near Radicondoli, west of Siena.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

Excellent 5/5 

Short stays welcome

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from £296 /night

£2067 - £3224 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
EASTER SPECIAL 40%OFF- SPECIAL OFFERS 2014!! More details inside. Beautiful villa in panoramic position with private pool, Hot Tub. 10-12persons.Peaceful location, ideal for families or groups seeking relaxation. 5 bedrooms / 5 bathrooms. Only 15km from Siena. Price all included, no extra charges and costs!!!  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 18

Min stay varies

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Key info:

  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Prestigious villa in the heart of Tuscany at 15 km from San Gimignano. renowned world over for it’s charm, and Beauty.  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Charming villa rental in Siena, Podere San Pietro is a typical stone country house, with wood beams and traditional Tuscan style furnishings.  …see more

14 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £266 /night

£1860 - £1934 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Ancient country home set in panoramic position amidst the rolling Sienese hills.The villa is situated on two floors both with external entrance.  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £160 /night

£1120 - £1620 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Villa Brolio is a renovated independent country house close to Siena in the Chianti area. From the house, surrounded by vineyards and olive groves, guests can enjoy beautiful views of the Tuscan countryside.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 10

Min stay varies

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Siena villa dolce collina, a renovated barn is situated in privileged position a stones throw from the renowned historic town of Siena, nestled amidst the peaceful green Tuscan hills spread with olive groves.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 16

Excellent 5/5 

3 Nights min stay

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from £213 /night

£1488 - £3678 / week

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Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Beautiful Tuscan detached villa with swimming pool near Siena to rent for sleeps up to-10-16-20-It is an ideal place for families to spend a relaxing holiday far from town noises among the peace of the country. A heaven of peace in the heart of Montagnola Senese at a stone's throw from Siena.  …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

8 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £92 /night

£643 - £841 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
among the woods and vineyards in the gentle hills of the chianti senese area, in the heart of one of the regions known throughout the world for its beauty and harmony, lies podere liliana. It was built in 1898 and has recently been wonderfully renovated and transformed into an elegant holiday home, ideal for those looking for relaxation, nature, good wines and excellent cuisine. They have made two apartments in the building, one on the ground floor and one on the first floor, offering a total of 10 beds, and which can also be rented together by one family group. The elegant furnishings have been carefully chosen, and the original bathrooms have been embellished with the addition of valuable materials, and everywhere there is a feeling of warmth and comfort. All of the rooms look onto the garden, which offers cool, shady areas at the foot of its tall mediterranean pine trees, offering also a large panoramic terrace and there is grass surrounding all of the house, making it an ideal place for contemplating in complete relaxation the olive groves, vineyards and woods around the house. Both of the apartments are spacious and come equipped with all modern conveniences (washing-machine, dishwasher, satellite-tv, hi-fi stereo/radio, cd and dvd players) all of which can make a stay in this wonderful house still more pleasant and relaxing. Podere liliana is in an ideal position for discovering all the old churches, medieval villages and castles in chianti and all of the large and small art towns in tuscany, easily reached from here. Nearest town: siena distance: 15 km in the event that the two apartments are booked together, 10% discount on the rental price.  …see more

8 Photos

Villa | 8 Bedrooms | sleeps 15

Min stay varies

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from £556 /night

£3889 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
the existence of this villa has been documented since the xviii century, but the current layout is the result of a transformation process that took place between 1870 and 1885, when the property belonged to a sienese aristocrat living in florence. In accordance with the spirit of renewal in taste and style that reigned in florence at that time, he built a completely innovative villa and garden complex, creating a romantic park similar to those being built in florence under the guidance of the architect poggi and the family of pucci gardeners. the villa has three floors and the façade is divided into three parts; the central part has three entrance portals. The property has recently been renovated and provided with air conditioning and wi-fi internet connection. The furnishings consist of antiques of different styles and from different periods, precious wall hangings and ornaments of great artistic value. whilst preserving its beautiful period features, the old kitchen is very professional and has all the latest modern accessories. the park covers an area of around three hectares and occupies a portion of sloping land in front of the villa that stretches to the south and to the west and is enclosed by a wall. It is divided into two parts: the first part consists of a flower garden situated on the higher ground, whereas the lower part, which includes a swimming pool for guests to use, with bathrooms and changing rooms, is a true romantic park with large wooded areas crossed by paths that suddenly open up to reveal stunning views of the tuscan hills. the water features are one of the particularly distinctive elements of the garden, consisting of several fountains, structures characterized by water play and, above all, the nymphaeum, also known as "venus' pool". The park also has a large brick and cast iron aviary, a lemon orchard and a rich collection of large citrus trees. the villa's location in the chianti countryside, just 9 km from siena, makes it a privileged and exclusive place. The villa is situated inside a large farm that produces excellent quality extra virgin olive oil and chianti wine.  …see more

18 Photos

Villa | 1 Bedroom | sleeps 7

7 Nights min stay

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from £207 /night

£1447 - £2067 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautifully restored villa with swimming pool on the edge of a small hamlet. sjfa;sdl fjks;f as;fkl jfk;lj asfklj fklafj klfj ;fklj dfk;lj afklja sfkalsjd faklfj kldfj as;fkl ja;fkl jas  …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

24 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £614 /night

£4294 - £6546 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
With a superb location in the heart of the Siena hills, Villa Stella dwells on a magnificent property just 15 minutes from Siena. The original house was built in the 17th century and has recently been converted in a remarkable retreat in the very heart of Tuscany. The  …see more

8 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £209 /night

£1463 - £1859 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
among the woods and vineyards in the gentle hills of the chianti senese area, in the heart of one of the regions known throughout the world for its beauty and harmony, lies podere liliana. It was built in 1898 and has recently been wonderfully renovated and transformed into an elegant holiday home, ideal for those looking for relaxation, nature, good wines and excellent cuisine. They have made two apartments in the building, one on the ground floor and one on the first floor, offering a total of 10 beds, and which can also be rented together by one family group. The elegant furnishings have been carefully chosen, and the original bathrooms have been embellished with the addition of valuable materials, and everywhere there is a feeling of warmth and comfort. All of the rooms look onto the garden, which offers cool, shady areas at the foot of its tall mediterranean pine trees, offering also a large panoramic terrace and there is grass surrounding all of the house, making it an ideal place for contemplating in complete relaxation the olive groves, vineyards and woods around the house. Both of the apartments are spacious and come equipped with all modern conveniences (washing-machine, dishwasher, satellite-tv, hi-fi stereo/radio, cd and dvd players) all of which can make a stay in this wonderful house still more pleasant and relaxing. Podere liliana is in an ideal position for discovering all the old churches, medieval villages and castles in chianti and all of the large and small art towns in tuscany, easily reached from here. Nearest town: siena distance: 15 km in the event that the two apartments are booked together, 10% discount on the rental price.  …see more

18 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £124 /night

£864 - £1278 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Villa Borgianni is a beautiful villa close to the walled city of Siena Surrounded by olive groves, Vineyards and cypress trees. The house was recently renovated and has all the modern comforts and furnished with antique furniture. There are 3 double bedrooms, fully  …see more

15 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £141 /night

£986 - £1527 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Nice independent house situated on the hillside near the village of Montebenichi in the Chianti area. The place is very quiet and has a beautiful panoramic view of the surrounding country with vineyards, olive groves and woods. Beautiful pool area with a nice ...  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 13

2 Nights min stay

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from £383 /night

£2681 - £3508 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Chiusdino Farmhouse is a truly fantastic place to stay, it includes cosy cottages for two or four grown ups and plenty of space for more cots and your pets too! It is really one of the most enchanting places we've come across, so far!  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £502 /night

£3513 - £4959 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Cecilia is an incredible rustic farmhouse villa in the heart of south Siena countryside with breathtaking panoramic views that enjoy the surrounding the historic town of Ceglie Messapica and a few kilometres from the enchanting town of Ostuni.  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

Min stay varies

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Key info:

  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • No pets allowed
Villa Le Cantine di Cerreto is one of our best villas in Italy for rent. Immersed in the heart of the countryside with beautiful swimming pool, this spectacular villa can comfortably sleep up to 14 people and is ideal for your vacation rental in Italy.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £873 /night

£6108 - £7802 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Standing position of this charming Villa let you enjoy the beautiful sunsets and romantic ambience in the shade of the beautiful extended vine pergola. The terrace provides you the best views overlooking the valley.  …see more

17 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £129 /night

£901 - £1364 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This lovely cottage has room to accommodate up to 4 people. It boasts a private garden and swimming pool, and it is the perfect house for a family or small group of friends planning a holiday in the countryside.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £142 /night

£992 - £1612 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Villa del Palio is a modern, luxurious villa in the heart of Tuscany and perfect for a getaway to explore the wonderful Siena  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £331 /night

£2315 - £3720 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This villa is the ideal holiday accommodation for a family or large group with its five bedrooms and bathrooms, lovely gardens and swimming pool, and best of all, its fabulous location just 3km from Siena. Also ideal for weddings and special events.  …see more

16 Photos

Villa | 10 Bedrooms | sleeps 24

Min stay varies

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from £2 /night

£11 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Montebenichi 20 - 26 pers. A luxury villa. 10 bedrooms + 6 p. 10 en-suit bathrooms. kitchen. living room, dining room, terass. Internet access  …see more

18 Photos

Villa | 5 Bedrooms | sleeps 16

2 Nights min stay

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from £87 /night

£605 - £693 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Exclusive estate on top of a green hill, the image that you have is to be completely isolated from the world, from the pool and terrace overlooking a panoramic view of Siena and unique, just 4 km away and do at your disposal all the civilizations that you want!  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 5

1 night min stay

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from £126 /night

£877 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
L'antica scuderia che un tempo veniva usata nel borgo di Certano oggi è stata completamente rinnovata e rappresenta il luogo ideale per una vacanza nella dolce campagna toscana  …see more

Siena is a beautiful Tuscan city that boasts some of Italy's finest architecture, from the Romanesque Duomo to the shell shaped Piazza del Campo. The latter is the location of the annual Palio, one of the most exciting events in Italy's calendar, when a fiercely fought horse race sweeps around the square.