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468 Holiday homes in Siena Province

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Filters applied: Private pool (468)

468 Results  |  
20 Photos

Cottage | 2 Bedrooms | sleeps 8

Very Good 4.5/5 

7 Nights min stay

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from £83 /night

£579 - £1447 / 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
Characteristic stone built house with private pool in Tuscany. Ideal for families and couples seeking relaxation. Panoramic position.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £182 /night

£1271 - £1621 / week

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Late Deal: save up to €425 (approx. £351)

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Thanks to its superb location is the ideal starting point for visiting the Val d'Orcia and Chianti hills, with its medieval towns such as Cortona, Montepulciano, Pienza, Montalcino and from there up to and San Gimignano and the beautiful art cities of Florence and Siena On demand services: Tranfer and Taxi service Wine and Olive Oil Tastings Cooking Lessons Dinners  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £182 /night

£1271 - £1534 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Thanks to its superb location is the ideal starting point for visiting the Val d'Orcia and Chianti hills, with its medieval towns such as Cortona, Montepulciano, Pienza, Montalcino and from there up to and San Gimignano and the beautiful art cities of Florence and Siena  …see more

Featured properties

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

21 Photos

Villa | 15 Bedrooms | sleeps 37

3 Nights min stay

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from £1417 /night

£9918 - £11571 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Luxury Villa seventeenth century, Private Chapel , private pool 10x20, sauna,Kitchen pool area Ideal location for weddings and parties Luxury villa, Ideal location for weddings and parties  …see more

24 Photos

Castle | 6 Bedrooms | sleeps 14

Min stay varies

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from £94 /night

£658 - £3592 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Castle, tuscany, italy, swimmingpool, bed and breakfast, gaiole in chianti, events, wedding, private castle, private villa, Yoga, wine  …see more

21 Photos

Apartment | 4 Bedrooms | sleeps 9

Excellent 5/5 

7 Nights min stay

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from £238 /night

£1665 / 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
An amazing holiday in the moast beautiful area of Tuscany, in the natural park of the Val d'Orcia, near Montalcino, Pienza, Siena, Montichiello, Bagno Vignoni. A quiete, relaxing garden with swimming pool, a charming, cosy and comfortable apartment in an ancient villa.  …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 | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £231 /night

£1612 - £3116 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
A splendid home in one of the most beautiful areas of Tuscany. This lovely farmhouse is situated in the heart of the Chianti region on a wine producing estate with a breathtaking view of the private vineyards just 1km from the characteristic borgo of Radda in Chianti.  …see more

22 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £48 /night

£331 - £414 / 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
Outside of the Magione Agriturismo, a large, fenced garden will allow children to play in complete safety, while also offering the opportunity to dine outside enjoying the barbecues for guests.  …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

Farmhouse | 11 Bedrooms | sleeps 24

Short stays welcome

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from £558 /night

£3900 - £8970 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
1700's farmhouse with breathtaking views over the Siena hills with a pool overlooking miles of countryside  …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

24 Photos

Villa | 9 Bedrooms | sleeps 18

Very Good 4/5 

2 Nights min stay

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from £808 /night

£5651 - £6089 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Ideal family and wedding Tuscan villa with private chlorine free pool. Tucked away yet not isolated. All amenities in the nearby village, walking distance. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …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

23 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £280 /night

£1959 - £3831 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Maramai, now a charming country house, used to be a small farm with 3 separate buildings. It is named after the Tuscan farmer’s family who lived there until the early ’70s.  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

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from £119 /night

£827 - £1901 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Villa La chiesina is ideal for families, for groups of friends and for all those who prefer to spend their holidays in well-appointed, welcoming and private surroundings. They offer an exclusive peaceful location that makes each stay in Tuscany pleasant and relaxing. The villa and the pool are let with the exclusive use  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £121 /night

£845 - £1940 / 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

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 | 6 Bedrooms | sleeps 12

Min stay varies

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from £613 /night

£4290 - £5720 / 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
An ancient farmhouse dating back to 1846 that lies in an agricultural farm that extends over a surface of 150 hectares. Every year our olive grove produces a tasty oil that can be tasted and purchased during your stay.  …see more

14 Photos

Villa | 6 Bedrooms | sleeps 12

Min stay varies

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Beautiful private holiday villa rental situated in the hills surrounding the characteristic mediaeval town of Radicondoli just 3 km away from the town itself.  …see more

11 Photos

Villa | 6 Bedrooms | sleeps 14

Min stay varies

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Splendid Tuscan Castle which dates back to the year 1000, perched on the edge of a tiny hamlet, immersed in one of the most beautiful scenic havens in the Chianti region and surrounded by breathtaking panorama of the soft rolling vineyards.  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

Min stay varies

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Characteristic Tuscan country home in panoramic position, near the small town of Rigomagno between Cortona and Siena.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Good 3/5 

Short stays welcome

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from £398 /night

£2781 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
In Tuscany, a delightfully restored farmhouse becomes designer's vacation spot.; 5 Bedrooms, Sleeps 10; Offers a open/ or covered heated pool for year around pleasure. Enjoy the beautiful views, the village of San Cassiano dei Bagni and Chianti, Siena and Tuscany.  …see more

23 Photos

Villa | 9 Bedrooms | sleeps 9

2 Nights min stay

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from £871 /night

£6091 - £6563 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Villa Leccio is a world apart set in a charming and peaceful place where guests can truly relax and rediscover a calmer pace of life, away from the city. Our area offers breathtaking panoramas, countless daily outings and still preserves an unspoiled wilderness.  …see more

18 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £288 /night

£2015 - £4994 / week

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Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
The villa is located 800 meters from a traditional Tuscan restaurant and four kilometers from the nearest village of Montepulciano where you'll find a few shops, restaurants, and a market. Nearby: Pienza, Montefollonico, Bagno Vignoni, Cortona, Orvieto, Castiglion del Lago, S.Quirico, Montalcino  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Short stays welcome

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from £213 /night

£1490 - £3001 / week

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Key info:

  • Nearest beach 200 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Due to the central geographical position of Villa Pietra del Diavolo you can spend a day touring famous cities rich in history, culture, architecture and artistic works such as Siena (km 45), Arezzo (km 50), Firenze (km 110), Perugia (km 70), Roma (km 150). Croce di Febo take care of our land according to the traditions of organic agricolture respecting the soil.  …see more

20 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Very Good 4.5/5 

Short stays welcome

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from £172 /night

£1200 - £2750 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Beautiful Tuscan home, lovingly restored for maximum seclusion and relaxation. With masses of character, this is a truly wonderful old large farmhouse, with large grounds and plenty of outside easting, snoozing and relaxing areas The large pool house overlooks the swimming pool and is perfect for long lazy lunches out of the direct sun  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £149 /night

£1041 - £1735 / week

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Key info:

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

24 Photos

Villa | 6 Bedrooms | sleeps 12

4 Nights min stay

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from £603 /night

£4215 - £6116 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Villa Magda is a luxurious villa in San Gimignano, and is perfect for a large group of family or friends that appreciate tranquility, privacy, and beautiful natural surroundings.  …see more

24 Photos

Villa | 12 Bedrooms | sleeps 22

7 Nights min stay

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from £375 /night

£2620 - £4496 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This elegant Monteroni d'Arbia villa for 22 people, with 12 bedrooms and 9 bathrooms, is ideal for large families. Located in Tuscany, Italy, this pet-friendly villa offers a swimming pool and an internet connection.  …see more

20 Photos

Villa | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £1115 /night

£7802 - £15364 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This modern tastefully furnished villa, can accommodate 18 people and consists of main building and two annexes. This awe-inspiring villa is located in Sarteano valley, where “The English Patient” and “Under the Tuscan Sun” were filmed.  …see more

20 Photos

Villa | 12 Bedrooms | sleeps 24

Excellent 5/5 

7 Nights min stay

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from £591 /night

£4133 - £5786 / 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
Tuscan private luxurious Villa, stone built, private pool, jacuzzi, 12 bedrooms, 12 bathrooms, up to 24 people private park, organic olive oil , garden, terrace. Ideal for big family or big group of friends, weddings, meetings  …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

24 Photos

Villa | 6 Bedrooms | sleeps 11

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 essential
  • No pets allowed
  • Private garden
Villa Alba is a 600 square-meter (approximately 6,458 square feet) and two-storey house in the countryside which sleeps eleven people. The villa has a private garden and a swimming pool. 20 km (12.4 miles) away from Siena and 80 km (49  …see more

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

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

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

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

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

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

24 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £78 /night

£542 - £1807 / week

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Key info:

  • Nearest beach 50 km
  • 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

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

16 Photos

Villa | 8 Bedrooms | sleeps 16

2 Nights min stay

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from £728 /night

£5092 - £7920 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Just six kilometres from the Renaissance masterpiece town of Pienza, yet light years away from the stresses of modern living, this luxury 8-bedroom farm conversion has the cosiest of interiors, the most luxurious of finishes and the warmest of welcomes awaiting.  …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

16 Photos

Villa | 5 Bedrooms | sleeps 16

7 Nights min stay

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from £682 /night

£4769 - £7860 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Fontanelle is without doubt one of our loveliest Tuscan properties. It is located to the west of Montalcino, an area renowned for its beauty and for its wines, especially the famous Brunello di Montalcino. The property is in a spectacular position, surrounded by viney  …see more

9 Photos

Villa | 7 Bedrooms | sleeps 16

7 Nights min stay

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from £189 /night

£1320 - £2306 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
This former farmhouse is situated along the old road Cassia, 5 km. away from Radicofani in a panoramic and peaceful area not so far away from the Spa of San Casciano Dei Bagni and Bagni San Filippo. This holiday house gives a confortable atmosphere to all ...  …see more

7 Photos

Villa | 1 Bedroom | sleeps 3

7 Nights min stay

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from £67 /night

£468 - £957 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Holiday house for 3 persons, with swimming pool , in San Gimignano  …see more

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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