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168 Holiday homes in Siena Province

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168 Results  |  
21 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £59 /night

£408 - £738 / 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

24 Photos

Villa | 9 Bedrooms | sleeps 18

3 Nights min stay

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from £182 /night

£1272 - £2396 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
"Villa Palazzone" is a charming country house set in the Siena province in the heart of a large estate of 153 hectares. It is very close to the beautiful little towns of Sarteano, Cetona and Città della Pieve and within 30 minutes from the lakes Trasimeno and Bolsena.  …see more

21 Photos

Villa | 8 Bedrooms | sleeps 12

Short stays welcome

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from £388 /night

£2714 - £4910 / 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 £2546 /night

£17820 - £23760 / 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

24 Photos

Apartment | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £84 /night

£582 - £1235 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
"BACCHINO IN THE CHIANTI" is located in the center of the Chianti geographic area where they produce the famous and superb wine Chianti Gallo Nero, between Gaiole in Chianti (5 km), Radda in Chianti (7 km) and Castellina in Chianti.  …see more

6 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £55 /night

£382 - £891 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Aroun  …see more

18 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £84 /night

£586 - £908 / 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

20 Photos

Farmhouse | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £686 /night

£4800 - £6880 / 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

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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Late Deal: save up to £469

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

18 Photos

Villa | 7 Bedrooms | sleeps 15

7 Nights min stay

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from £383 /night

£2680 - £4400 / 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

16 Photos

Cottage | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £132 /night

£920 - £1160 / 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 £532 /night

£3720 - £7000 / 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

19 Photos

Villa | 5 Bedrooms | sleeps 11

7 Nights min stay

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from £606 /night

£4240 - £7840 / 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

Manor House | 9 Bedrooms | sleeps 18

7 Nights min stay

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from £1000 /night

£7000 - £13760 / 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

21 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Very Good 4.5/5 

3 Nights min stay

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from £61 /night

£424 - £756 / 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 | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £80 /night

£560 - £1200 / 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

16 Photos

Farmhouse | 3 Bedrooms | sleeps 6

1 night min stay

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from £136 /night

£950 - £1103 / 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

19 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £73 /night

£509 - £806 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Offering an outdoor pool and free bikes, Villa Sant'Alberto is located in Monteroni d'Arbia, in the heart of the Crete Senesi hills. Free Wi-Fi access is available in this farm stay. This farm stay is 15 km from Siena.  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £280 /night

£1960 - £3040 / 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

24 Photos

Villa | 5 Bedrooms | sleeps 10

Good 3/5 

Short stays welcome

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from £385 /night

£2692 / 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

House | 1 Bedroom | sleeps 4

1 night min stay

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from £70 /night

£490 - £800 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
  • Private garden
Casa Adalmina A 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 four people. From Casa Adalmina A you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

House | 3 Bedrooms | sleeps 9

1 night min stay

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from £130 /night

£910 - £1400 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
  • Private garden
Casa Adalberto A is a pleasant and spacious two-story apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps nine people. From Casa Adalberto A you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £72 /night

£504 - £560 / 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

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
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Emide D is a graceful apartment in a history-rich eighteenth-century estate. It sleeps four people. From Casa Emide D you will enjoy a marvelous view of the greenery. Casa Emide D is 80 square meters (860 square feet)  …see more

18 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

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from £86 /night

£600 - £1280 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Giobatta O is a countryside house of 120 square meters ( about 1,291 square feet) which sleeps six people. It has a private garden, a swimming pool, a tennis court, and a shared garden  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £103 /night

£716 - £960 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Appartamento Il Riccio A is a romantic and welcoming two-story apartment surrounded by vineyards and olive groves. It sleeps four people. From Appartamento Il Riccio A you will enjoy an enchanting view of the Tuscan countryside and of the towers of San Gimignano  …see more

20 Photos

House | 6 Bedrooms | sleeps 12

1 night min stay

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from £600 /night

£4200 - £5600 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Cherubina is a splendid sixteenth-century three-story villa located on top of a small hill. It sleeps 12 people. From Villa Cherubina you will enjoy a wonderful view of the Senesi hills. Villa Cherubina is 500 square meters (5380 square feet)  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £79 /night

£552 - £1080 / 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

20 Photos

Apartment | 3 Bedrooms | sleeps 5

1 night min stay

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from £83 /night

£576 - £1160 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Giobatta A is a 100 square meter (approximately 1075 square feet) apartment in the countryside for five people, with a private patio and a shared garden and swimming pool. It is 20 km (approximately 12 miles) from Siena and 80 km (50 miles) from Florence  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £58 /night

£404 - £476 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Sibilla E is a characteristic 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  …see more

20 Photos

House | 3 Bedrooms | sleeps 9

1 night min stay

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from £130 /night

£910 - £1400 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
  • Private garden
Casa Adalmina B is a pleasant and spacious three-story apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps nine people. From Casa Adalmina B you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

House | 3 Bedrooms | sleeps 8

1 night min stay

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from £90 /night

£624 - £976 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria E is a 100-square-meter (1076 square feet) house on a hill which sleeps eight people. It features a private patio and shared garden and swimming-pool. It is part of a small medieval hamlet consisting of stone houses restored as vacation homes  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £79 /night

£552 - £1080 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Giobatta N is a 80 square meter (approximately 860 square feet) house in the countryside for four people, with a private terrace and shared swimming pool, tennis court and garden  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 18

1 night min stay

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from £738 /night

£5160 - £5560 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Larice Grande is a characteristic two-story age-old farm house made of stone. It sleeps 16 people. From Villa Larice Grande you will enjoy a fascinating view of the Valley and of the hills. Villa Larice Grande is 600 square meters (6460 square feet)  …see more

20 Photos

Apartment | 9 Bedrooms | sleeps 18

1 night min stay

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from £421 /night

£2944 - £3680 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Tristano Grande is a beautiful villa of 360 square meters (about 3875 square feet), for eighteen people, with pool, garden, patio and terraces, and a splendid view over the valley and of San Gimignano  …see more

20 Photos

Apartment | 4 Bedrooms | sleeps 8

1 night min stay

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from £101 /night

£704 - £1256 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Quercia is an apartment of 120 square meters (approximately 1290 square feet) which sleeps eight persons. It has a porch and a splendid view of the Tuscan hills. Guests of the apartment can use a shared garden and a shared swimming pool  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £74 /night

£512 - £752 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Prosperina A is a characteristic two-story apartment created inside an ancient watch tower. It sleeps four people. From Appartamento Prosperina A you will have a pleasant view of the Valley and of the hills  …see more

20 Photos

Apartment | 6 Bedrooms | sleeps 12

1 night min stay

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from £528 /night

£3696 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Beata A is a splendid apartment that covers the entire top floor of an ancient country manor made of stone. It sleeps 12 people. From Villa Beata A you will enjoy a charming view of the Tuscan countryside and of the hills  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £74 /night

£512 - £752 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Prospero A is a pleasant and spacious apartment surrounded by meadows and by green hills. It sleeps four people. It is appoximately 50 square meters (540 square feet). It features a shared swimming pool, a shared garden and winter heating  …see more

14 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

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from £133 /night

£928 - £1092 / 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

Villa | 8 Bedrooms | sleeps 16

1 night min stay

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from £560 /night

£3920 - £4640 / 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

22 Photos

Villa | 6 Bedrooms | sleeps 12

1 night min stay

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from £330 /night

£2304 - £2880 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Tristano is a beautiful villa of 360 square meters (about 3875 square feet), for twelve people, with pool, garden, patio and terraces, and a splendid view over the valley and of San Gimignano  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £86 /night

£596 - £873 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Appartamento Reginaldo C is an elegant and welcoming apartment that is part of a villa in the characteristic style of the Tuscan countryside. It sleeps four people  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

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from £114 /night

£792 - £1100 / 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 3

1 night min stay

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from £58 /night

£400 - £584 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Prospero E is a graceful apartment surrounded by the vegetation. It sleeps four people. From Casa Prospero E you will have a view of the swimming pool and of the garden and of the surrounding countryside. Casa Prospero E is 100 square meters (1076 square feet)  …see more

20 Photos

House | 1 Bedroom | 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
  • No pets allowed
  • Private garden
Casa Adalberto B is a pleasant and spacious two-story 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 B you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

House | 2 Bedrooms | sleeps 6

1 night min stay

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from £67 /night

£468 - £736 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Saveria D 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

23 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £95 /night

£664 - £936 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Casa Genziana A is a characteristic and welcoming one-story apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps six people. From Casa Genziana A you will enjoy a view of the Tuscan countryside  …see more

20 Photos

House | 5 Bedrooms | sleeps 12

1 night min stay

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from £286 /night

£2000 - £2600 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Adalia is an elegant and welcoming apartment that covers the entire top floor of an ancient country manor built on a hillside, surrounded by meadows and woods. It sleeps 12 people. From Villa Adalia you will enjoy an enchanting view of the Senesi hills  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 3

7 Nights min stay

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from £65 /night

£450 - £720 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
  • Private garden
Casa Miretta A is a graceful two-story apartment that is part of an ancient country house located on top of a small hill. It sleeps three people. It is appoximately 60 square meters (645 square feet)  …see more