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468 Holiday homes in Siena Province

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Filters applied: Private pool (468)

468 Results  |  
19 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

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from £566 /night

£3961 - £6083 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
This beautiful, rustic villa is built on the side of a hill and surrounded by vineyards and woods. The villa is at the heart of an agricultural estate that produces organic wine and extra virgin olive oil. Good food, wine and relaxation await you in the heart of Tuscany  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £298 /night

£2083 - £3463 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
A beautiful 17th century casale (traditional Tuscan farmhouse) comprised of 3 apartments and 2 bedrooms intercommunicating and a panoramic swimming pool with a private garden.  …see more

11 Photos

House | 6 Bedrooms | sleeps 12

Short stays welcome

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from £709 /night

£4959 - £6327 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
In this paradise, guests can enjoy deep blue skies, starry nights and silence, a unique and rare commodity nowadays. The property offers: - spacious, fully equipped family kitchen - living room with large fireplace  …see more

Featured properties

24 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £233 /night

£1627 - £2711 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Holiday house for 12 persons, with swimming pool , in Siena  …see more

18 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £275 /night

£1925 - £3800 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Siena countryside family villa – Conveniently located south of Siena, Biancaserena is a modern villa surrounded by the typical, idyllic Tuscan landscape.  …see more

17 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £453 /night

£3169 - £4300 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Casa Olive enjoys the peace and beauty of the Tuscan countryside, but with the convenience of a location within village of Castelmuzio. The large grounds include a private infinity swimming pool, and secluded gardens with dramatic views.  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £257 /night

£1795 - £2695 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Villa near Montepulciano - this restored Tuscan farmhouse with private pool is set in a picturesque location near the lovely town of Montepulciano.  …see more

13 Photos

Apartment | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £84 /night

£585 - £849 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Attractive apartment for 8 persons, with swimming pool , in San Gimignano  …see more

19 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £886 /night

£6199 - £7976 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Recently restored to the highest standard, the Villa is a deluxe country house in the beautiful Val D’Orcia in the South-Eastern part of the Siena province in Tuscany.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £135 /night

£940 - £1566 / week

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Key info:

  • Nearest beach 65 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Attractive holiday house for 5 persons, with swimming pool , in Siena  …see more

13 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £143 /night

£1000 - £1713 / 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
Lovely house in the heart of the Chianti area, just 15 km from Siena, situated in peaceful position even though a secondary road passes 50m away. The property is partly fenced-in and the swimming pool, just below the house ground, has a lovely view over the va...  …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

Villa | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £222 /night

£1553 - £3255 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Villa Santa Lucia is a fabulous modern country Villa, built on the Chianti hillside. The elegantly villa is comfortably furnished with beautiful antique Florentine furniture and modern pieces. There is high quality wooden parquet flooring, Venetian stucco walls and gla  …see more

19 Photos

Villa | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £298 /night

£2083 - £2264 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
The enchanting Villa Terrazzeria is a adorable villa set in the stunning Tuscany countryside.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

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from £140 /night

£974 - £1889 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Attractive holiday house for 9 persons, with swimming pool , in Siena  …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

12 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £123 /night

£861 - £1182 / week

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Key info:

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

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £677 /night

£4734 - £5118 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Luxury holiday house for 16 persons, with swimming pool , in Chiusi - Chianciano  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 16

1 night min stay

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from £579 /night

£4050 - £4794 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Ciliegia is a charming three-story historical villa surrounded by a wonderful age-old park. It sleeps 16 people. It is appoximately 600 square meters (6460 square feet). It features a private swimming pool, a private garden and winter heating  …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

11 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £225 /night

£1570 - £2440 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Villa near Monteriggioni : Located in the heart of Tuscany, to the south of Florence, Villa Gianni is an attractive, small property, recently renovated and well furnished throughout. There are classic Tuscan views of vineyards and rolling hills from around the villa.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

7 Nights min stay

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from £246 /night

£1717 - £3434 / week

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Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Attractive holiday house for 14 persons, with swimming pool , in San Gimignano  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 11

7 Nights min stay

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from £125 /night

£871 - £2810 / week

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Key info:

  • Nearest beach 40 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
This villa is located just 2 km from the beautiful town of Volterra in a place of absolute tranquillity: an old Tuscan house with stone exterior that has been completely renovated and divided into two separate, comfortable flats. The villa is ideal for two fam...  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

7 Nights min stay

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from £233 /night

£1627 - £2711 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Holiday house for 8 persons, with swimming pool , in Chianti  …see more

16 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £162 /night

£1130 - £1612 / week

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Key info:

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

12 Photos

Villa | 8 Bedrooms | sleeps 15

7 Nights min stay

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from £467 /night

£3265 - £5405 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
A quiet Tuscan rental villa is a country house, built between the XV and XVI centuries, full of atmosphere and immersed in the classical Sienese landscape of, oak and holm oak woods, olive groves, vineyards and fields of wheat.  …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

17 Photos

House | 6 Bedrooms | sleeps 14

7 Nights min stay

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from £467 /night

£3265 - £5405 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
The house is named for a nearby spring and is surrounded by lawns and fruit trees including lemon trees. One area is devoted to aromatic herbs and unites the house to the annexe. Splendid panoramic position  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £467 /night

£3265 - £5405 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
This stone vacation house was originally inhabited by a large family of farmers who worked for the monks of the nearby Abbey of Spineto. Excellent furnishing. Comfort and very peaceful atmosphere  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £165 /night

£1153 - £1843 / 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
In the middle of the green Tuscan hills, just a short distance from the Etruscan necropolis of Chiusi and Chianciano Terme, is the holiday home Podere San Gaetano situated. It has an overlooking position from which you can admire a wonderful panorama on the su...  …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

24 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £314 /night

£2197 - £4119 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Luxury holiday house for 12 persons, with swimming pool , in Chianti  …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

24 Photos

Villa | 2 Bedrooms | sleeps 8

7 Nights min stay

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from £80 /night

£560 - £1868 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Attractive holiday house for 8 persons, with swimming pool , in Siena  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £91 /night

£633 - £2109 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Attractive holiday house for 6 persons, with swimming pool , in Siena  …see more

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £142 /night

£992 - £2404 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • May take pets – please enquire
This beautiful, detached farmhouse has been carefully restored by the architect owner to the highest standards. He has maintained the original structure, while adding modern design ideas.  …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

18 Photos

Villa | 8 Bedrooms | sleeps 14

7 Nights min stay

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from £1181 /night

£8265 - £9505 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Between the two small towns of Radda and Gaiole in Chianti, two historical sites for the production of Chianti Classico, right in the heart of Tuscany, there lies Fattoria of Villa Divina, a large farm of approx 500 acres  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

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from £89 /night

£620 - £1323 / week

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Key info:

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

10 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £119 /night

£831 - £1656 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Holiday house for 8 persons, with swimming pool , in San Gimignano  …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

24 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £78 /night

£542 - £1807 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Attractive holiday house for 5 persons, with swimming pool , in Siena  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

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

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £166 /night

£1158 - £2397 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
For rent: This villa is situated spectacularly, on a hill just south of Siena. It is a traditional villa, luxurously renovated and furnished with a modern look. Private pool and large garden. Good, central location. Fabulous view of the medieval skyline of Siena.  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £517 /night

£3616 - £5372 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
If a villa holiday in Tuscany is calling to you, take a closer look at Villa Magna. This property provides ample room for twelve guests, offering six beautiful bedrooms and a variety of other features you'll fall in love with on first sight.  …see more

13 Photos

Villa | 5 Bedrooms | sleeps 13

7 Nights min stay

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from £141 /night

£981 - £2083 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Holiday house for 13 persons, with swimming pool , in Cortona  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £929 /night

£6500 - £8350 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Large villa near Siena - Recently restored to a very high standard, La Gioconda is a beautiful country house set amid the stunning unspoilt countryside of the Val d'Orcia in the south eastern part of the Siena region.
 …see more