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161 Holiday homes in Siena Province

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161 Results  |  
21 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £61 /night

£421 - £763 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Why the Owner Chose Buonconvento: This area of Tuscany is intensely beautiful and within easy reach of many of the most significant cultural sites in Italy. In addition I love golfing and 30 min away there are marvelous golf courses such as La Bagnaia, Tuscany Golf. In Summer time, Prisca House guest can have a swim in Buonconvento huge communal pool (10 minutes aways)  …see more

20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £182 /night

£1272 - £2067 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Chianti - well situated farmhouse with beautiful views  …see more

21 Photos

Villa | 8 Bedrooms | sleeps 12

Short stays welcome

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from £401 /night

£2804 - £5073 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Floren  …see more

Featured properties

24 Photos

Villa | 14 Bedrooms | sleeps 27

7 Nights min stay

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from £2630 /night

£18410 - £24546 / 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 exclusive luxury villa nestled in the hills of the Tuscan countryside in the south of the province of Siena offers top-quality accommodation completed by first-class services and panoramic views in a natural biogenetic reserve in the Val di Merse.  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £105 /night

£732 - £1135 / week

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Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
In the heart of Valdorcia, on the west side of Mt Cetona, our “Borgo” has been dominating for more than 400 years this exceptional valley that the UNESCO declared to be one of humankind’s treasures.  …see more

9 Photos

House | 2 Bedrooms | sleeps 4

Min stay varies

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from £95 /night

£662 - £992 / week

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Key info:

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

16 Photos

Cottage | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £136 /night

£951 - £1199 / week

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Key info:

  • Nearest beach 40 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
The cottage is in the heart of the hamlet made up of the 14th century castle situated in one of the most spectacular positions in the territory of San Casciano dei Bagni, overlooking the Valdichiana and the hills of Umbria. On request: pottery classes  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £549 /night

£3843 - £7232 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Incredible views over the Tuscan countryside. Beautiful garden with swimming pool heated by solar panels.  …see more

18 Photos

Villa | 7 Bedrooms | sleeps 15

7 Nights min stay

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from £396 /night

£2769 - £4546 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
A quiet country house,(XVIth century), full of atmosphere immersed in the classic Sienese landscape. The swimming pool is beautifully set in a garden and enables you to completely unwind and relax. The interior is well furnished and elegant.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 11

7 Nights min stay

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from £626 /night

£4381 - £8100 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Swimming pool (13x4 meters) with heated changing room, garden, 30 hectares of private wood and orchard.  …see more

20 Photos

Farmhouse | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £709 /night

£4959 - £7108 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Fantastic farmhouse with heated pool. Activities organized and chef, babysitter and driver available.  …see more

20 Photos

Manor House | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £1034 /night

£7232 - £14215 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Beautiful stone manor house with heated swimming pool and outdoor heated jacuzzi.  …see more

16 Photos

Farmhouse | 3 Bedrooms | sleeps 6

1 night min stay

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from £141 /night

£982 - £1139 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
Apartment (3 bedrooms) in old Tuscan Cottage with panoramic view and swimming pool. Just restored and finely furnished with well equipped kitchens. Podere Sant'Alessandro is immersed in beautiful scenery, and is among woods, vineyards, medieval villages and castles.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £83 /night

£579 - £1488 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Chianti farmhouse, Gaiole in Chianti, pool, Barn, Gite, Demeure de charme, piscine, cités d'art, barn, la casa in chianti, Casa Forcheri Fico for 6 people Cipresso for 4/5 p Olivo for 4-6 p Cipresso+Olivo, maximum 11p  …see more

14 Photos

Apartment | 10 Bedrooms | sleeps 20

Excellent 5/5 

3 Nights min stay

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from £132 /night

£920 - £9199 / week

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Key info:

  • Nearest beach 68 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Wonderfull apartments for unforgettable holiday in Montalcino, Tuscany, Italy. Wine tasting in the neighbouring wineries and bicycle or hiking tours in the World Heritage Site Val d'Orcia - you have the choice!  …see more

21 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Very Good 4/5 

3 Nights min stay

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from £63 /night

£439 - £781 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Self-catering child-friendly Tuscan farm building. On 10 hectares of wooded hillside, outside midieval fortress town of San Gimignano. Large shared pool, and private shaded terrace for al fresco dining. Perfect base for exploring San Gimignano, Siena and Florence. Family-friendly two-bed, two-bath restored Tuscan farm with shared pool sleeps 5 just outside San Gimignano  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 20

Excellent 5/5 

1 night min stay

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from £313 /night

£2191 - £3417 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Poggio Lungo is set amid the rolling green hills of Tuscany, in a peaceful setting where you can enjoy total relax during your stay. It has two kitchens, a dining room, a lounge with satellite tv, there are 9 bedrooms and a further double bedroom in an annexe.  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £290 /night

£2025 - £3141 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Beautiful independent restored villa (400 sqm) sleeping 10 with private pool, astro turf tennis court, gardens. Located in panoramic position on a Chianti Hillside only 5km from Castellini in Chianti. The property is surrounded by a well-maintained large garden.  …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

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

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £60 /night

£414 - £604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Prospero C is a welcoming two-story apartment surrounded by the vegetation. It sleeps five people. From Casa Prospero C you will have a pleasant view of the Tuscan hills and of the surrounding countryside. Casa Prospero C is 60 square meters (645 square feet)  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

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from £98 /night

£686 - £910 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Raniero B is a bright and sunny two-story apartment situated a few miles from the historic center of Siena. It sleeps five people. From Appartamento Raniero B you will enjoy a broad view of the Chianti hills  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £60 /night

£414 - £579 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Villa Davide D is a characteristic apartment surrounded by the vegetation. It sleeps four people. From Villa Davide D you will enjoy a pleasant view of the vegetation. Villa Davide D is 50 square meters (540 square feet)  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £65 /night

£455 - £604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Flora is a romantic apartment of 32 square meters (345 square feet), for two people. It is part of an ancient stone house, and it has a patio as well as a shared swimming pool and a park of 4000 square meters (1 acre)  …see more

20 Photos

House | 6 Bedrooms | sleeps 15

1 night min stay

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from £215 /night

£1500 - £2700 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Calatea is a characteristic three-story age-old farm house with strong character, which derives from it actually being restored from an old kiln. It sleeps 15 people. From Villa Calatea you will enjoy a splendid view of the Senesi hills and of the vineyards  …see more

20 Photos

House | 1 Bedroom | sleeps 2

1 night min stay

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from £55 /night

£381 - £587 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria N is a gracious 40-square-meter (about 430.5 square feet) house on a hill which sleeps two people. It features a private terrace and shared garden and swimming-pool  …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

Apartment | 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
  • No pets allowed
  • Private garden
Villa Beata D is a characteristic apartment made of stone. It sleeps two people. From Villa Beata D you will have a pleasant view of the surrounding countryside and of the vineyards. Villa Beata D is 35 square meters (375 square feet)  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £60 /night

£418 - £492 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Sibilla F is an apartment in the characteristic style of the Tuscan countryside. It sleeps two people. It is appoximately 40 square meters (430 square feet). It features a shared swimming pool, a shared garden and winter heating. You will be roughly 3 km (1  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £103 /night

£715 - £761 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Larice D is a characteristic apartment surrounded by the vegetation. It sleeps two people. From Appartamento Larice D you will enjoy a pleasant view of the garden and of the surrounding countryside  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £114 /night

£794 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Il Riccio C is a romantic and welcoming two-story apartment surrounded by vineyards and olive groves. It sleeps four people. From Appartamento Il Riccio C you will enjoy an enchanting view of the Tuscan countryside and of the towers of San Gimignano  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £60 /night

£414 - £604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Prosperina B is a characteristic apartment created inside an ancient watch tower. It sleeps four people. From Appartamento Prosperina B you will have a fascinating view of the Valley. Appartamento Prosperina B is 100 square meters (1076 square feet)  …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 C is a romantic 65-square-meter (about 700 square feet) apartment which sleeps two people. It features a view to the hills famous as 'Crete Senesi '. There is also a shared swimming pool and shared gardens  …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

14 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

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from £137 /night

£959 - £1129 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Sidonia is a pleasant and spacious apartment in the characteristic style of the Tuscan countryside. It sleeps six people. It is appoximately 90 square meters (970 square feet)  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £75 /night

£521 - £786 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria O is a gracious 60-square-meter (about 646 square feet) house on a hill which sleeps six people. It features a private terrace and shared garden and swimming-pool  …see more

20 Photos

House | 2 Bedrooms | sleeps 5

1 night min stay

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from £100 /night

£700 - £1100 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Adalberto C is a pleasant and spacious apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps five people. From Casa Adalberto C you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

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from £95 /night

£662 - £868 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Mela is an apartment of 56 square meters (about 600 square feet), for five people, with a patio, it also shares a pool and a 4000 square meter (about 1 acre) park  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £88 /night

£615 - £724 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Sibilla A is an apartment in the characteristic style of the Tuscan countryside. It sleeps four people. It is appoximately 60 square meters (645 square feet). It features a shared swimming pool, a shared garden and winter heating  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £60 /night

£414 - £579 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Villa Davide E is a splendid apartment surrounded by the vegetation. It sleeps four people. From Villa Davide E you will enjoy a wonderful view of the Tuscan countryside. Villa Davide E is 50 square meters (540 square feet)  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £82 /night

£571 - £1116 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Giobatta T is a 110 square meter (approximately 1180 square feet) house in the countryside for four people, with a private patio and shared swimming pool, tennis court and garden  …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

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £122 /night

£850 - £1220 / week

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Key info:

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

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £103 /night

£715 - £761 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Larice E is a graceful apartment built on a hillside, surrounded by meadows and woods. It sleeps two people. From Appartamento Larice E you will enjoy a pleasant view of the garden and of the hills  …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 £172 /night

£1199 - £2108 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Fragola is a graceful villa surrounded by meadows and by green hills. It sleeps six people. From Villa Fragola you will have a splendid view of the Senesi hills and of the Chiocciola Castle. Villa Fragola is 120 square meters (1290 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

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 B is a graceful apartment in a history-rich eighteenth-century estate. It sleeps four people. From Casa Emide B you will enjoy a marvelous view of the greenery. Casa Emide B is 70 square meters (750 square feet)  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £82 /night

£571 - £1116 / week

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Key info:

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

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