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2,535 Results  |  
24 Photos

Fort | 1 Bedroom | sleeps 3

3 Nights min stay

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from £104 /night

£727 - £808 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Romantic and charming 14th century fortress. Very authentic medieval atmosphere. Strategically located between Val d'Orcia and Crete Senesi, close to Montalcino, Montepulciano, Pienza and Siena. Shops at walking distance. Organic wine and extra virgin olive oil.  …see more

23 Photos

Fort | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £150 /night

£1050 - £1147 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Romantic and charming 14th century fortress. Very authentic medieval atmosphere. Strategically located between Val d'Orcia and Crete Senesi, close to Montalcino, Montepulciano, Pienza and Siena. Shops at walking distance. Organic wine and extra virgin olive oil.  …see more

15 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Very Good 4/5 

2 Nights min stay

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from £61 /night

£424 - £764 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
We are an old Tuscan farm half way between Siena and Florence, a few miles of a drive from Monteriggioni, San Gimignano, Volterra and the Chianti. We are located on the top of a hill, in a very quiet spot. Here you can enjoy the country with its beautiful landscape.  …see more

Featured properties

10 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £80 /night

£560 - £600 / week

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Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Enjoy Tuscany, in a unique village in a UNESCO world heritage site: access to art, good food and excellent wine.  …see more

13 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

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from £73 /night

£509 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Borgo in genuine Chianti town. Scenery perfect for hiking and biking. Proximity to Siena and Florence alongside other cultural and historical Chianti villages. Excellent local dining and wine tasting. Property provides easy access to spacious terrace and pool area.  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £43 /night

£297 - £382 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Charming, cozy and relaxing apartment in Cetona. Convenient parking, outside patio for sunbathing and dining alfresco, short walk to the piazza, all make this your ideal holiday choice.  …see more

15 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

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from £43 /night

£297 - £535 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
The apartment is located in an old Tuscan village, along with 4 other apartments. The farmhouse with swimming pool, indoor games room and outdoor pool, breakfast room, barbecue, selling local products, mountain biking and organic garden. You will also find farm animals.  …see more

14 Photos

Farmhouse | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £61 /night

£424 - £713 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Our farm is the only one with a horse on the property, offers a beautiful view, surrounded by green gardens, with a wood-burning oven in the central courtyard and have WI-FI internet access. We offer many services and activities of a different kind, for everyone.  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 4

5 Nights min stay

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from £73 /night

£505 / week

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Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Romantic one bedroom apartment in Elegant Liberty country village close to Siena medieval city. Picturesque courtyard and garden for outdoor dining.  …see more

15 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £49 /night

£340 - £624 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Our farm is the only one with a horse on the property, offers a beautiful view, surrounded by green gardens, with a wood-burning oven in the central courtyard and have WI-FI internet access. We offer many services and activities of a different kind, for everyone.  …see more

15 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £49 /night

£340 - £594 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Our farm is the only one with a horse on the property, offers a beautiful view, surrounded by green gardens, with a wood-burning oven in the central courtyard and have WI-FI internet access. We offer many services and activities of a different kind, for everyone.  …see more

6 Photos

Villa | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £158 /night

£1103 - £1527 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Unique villa in the area of Siena, pefect climatized and furnished with all comforts,The villa le Tortore offers private parking , private garden, exclusivity, access to the swimming pool, air conditioning, satellite Tv with Sky channels, PC with free dsl and wi-fi.  …see more

4 Photos

Apartment | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £91 /night

£636 - £848 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
The villa Podernovo offers a nice apartment called Il Forno, with stunning view on the sunflowers fields, with all comforts such air conditioning.  …see more

4 Photos

Apartment | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £97 /night

£679 - £1018 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
This the nice large apartment at the ground floor of our villa.  …see more

16 Photos

Farmhouse | 6 Bedrooms | sleeps 20

Excellent 5/5 

2 Nights min stay

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from £509 /night

£3562 - £4919 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Climatized villa with swimming pool, wi-fi,and TV with Sky channels, offers relax and fun at only 7 miles from Siena. The Count Filippo Fiorentini, English speaking will welcome you with a good glass of wine, in his villa.  …see more

9 Photos

Farmhouse | 4 Bedrooms | sleeps 16

2 Nights min stay

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from £364 /night

£2544 - £3392 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
The Podere Podernovo offers accomodation up to 16 people,with all comforts,as heating, air condititioning, Internet,wi-fi, Tv with Sky.The Count Fiorentini will welcome you in his farmhouse just 12 km south of Siena in the Arbia valley.  …see more

24 Photos

Farmhouse | 10 Bedrooms | sleeps 20

Short stays welcome

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from £509 /night

£3562 / 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
  • Private garden
The Wine Estate of Castelnuovo Tancredi has 3 stone farmhouses with a shared pool overlooking the gorgeous countryside. With the option to rent a farmhouse individually, or the entire property, it is ideal for vacation, weddings or even a family reunion! You haven't seen the real Tuscany until you see the Val d'Orcia. Wine tastings and cooking classes on site.  …see more

21 Photos

Farmhouse | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £206 /night

£1442 - £1781 / week

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Late Deal: save up to €770 (approx. £616)

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Self Catering Tuscan farmhouse with 4 large bedrooms in a cozy hamlet immersed in the surrounding countryside. Lovely shared pool. Al-fresco private garden dining and stunning views. Perfect for families with children! Wine tasting and cooking classes on site. The Pheasant farmhouse is the original house of the this antique hamlet surrounded by rolling Tuscan hills.  …see more

5 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £91 /night

£636 - £848 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
The Il Pino apartmnet is located at the first floor of the Podere Podernovo at San fabiano farmestate  …see more

19 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £223 /night

£1560 - £3000 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Elegant air-conditioned villa with private pool to rent close to Montepulciano – sleeps 6 From 2160€ to 3480€ a week  …see more

20 Photos

Farmhouse | 5 Bedrooms | sleeps 9

Short stays welcome

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from £124 /night

£864 - £1664 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Comfortable country house with private pool to rent near San Casciano dei Bagni – sleeps 9 From 1080€ to 2040€ a week  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £206 /night

£1440 - £2880 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Holiday villa with private pool and sauna within walking distance from Cetona – sleeps 9 From 1800€ to 3600€ a week  …see more

14 Photos

Villa | 6 Bedrooms | sleeps 12

3 Nights min stay

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from £343 /night

£2400 - £3600 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Large mansion with private pool to rent near Monteroni d'Arbia - sleeps 11 From 3000€ to 4500€ a week  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £485 /night

£3392 - £4522 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Ancient and noble mansion of the XVIII century overlooking Chianti hills, for a luxury and leisure stay in the hearth of Tuscany... Its location in the centre of Tuscany, a few km from the highway Firenze-Siena.  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 8

5 Nights min stay

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from £108 /night

£755 - £1408 / 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
In the heart of Tuscany, the Antica Canonica is a historical residence, excellently located for exploring the area and discovering the delights of Tuscany. Ideal for families seeking relaxation. Swimming-pool, hydro massage, exclusive garden. The original characteristics keep the old glamour and suggest the idea that the time has stopped.  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £176 /night

£1230 - £1484 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Charming farmhouse in Tuscany, the ideal starting point to visit the Val di Chiana and Val d'Orcia with its wonderful medieval towns such as Cortona, Montepulciano, San Quirico d'Orcia, Pienza, as well as Montalcino and San Gimignano and the beautiful art town of Siena. Situated in the heart of Tuscany, near the centre of the little town of Sinalunga.  …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

11 Photos

Cottage | 1 Bedroom | sleeps 2

1 night min stay

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from £97 /night

£679 - £848 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Agriturismo Podernuovo is an excellent place for a relaxing vacation. Independent and quiet, next to the owner's residence, has a wonderful 360° panorama looking the Crete Senesi hills with view over Siena in one side and Montalcino and Trequanda in the other side. Agriturismo Podernuovo is 10 km from the hot springs of Rapolano Terme, while Siena is 30 km away.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £45 /night

£310 - £586 / week

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Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa PoliFlora is a modern residence consists of two bedrooms and two bathrooms with a shared kitchen. The owners husband and wife Poli and Flora built the villa in 1988 and from there they guard with love the classic environment of the house surrounded by garden. Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site.  …see more

19 Photos

Farmhouse | 6 Bedrooms | sleeps 12

1 night min stay

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from £122 /night

£848 - £2120 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Beautiful Tuscan country house and cottage set on a natural terrace with commanding views of the Tuscan hills. Deep in the countryside with easy day trips to Florence, Sienna and Perugia.  …see more

21 Photos

Castle | 6 Bedrooms | sleeps 16

7 Nights min stay

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from £412 /night

£2880 - £3080 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Romantic castle with pool to rent near Montepulciano – sleeps 14+2 From 3300€ to 3850€ a week  …see more

7 Photos

Farmhouse | 3 Bedrooms | sleeps 7

5 Nights min stay

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from £170 /night

£1188 - £1951 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Silence, nice countryside, good food.Relax  …see more

21 Photos

Apartment | 3 Bedrooms | sleeps 7

Very Good 4.5/5 

3 Nights min stay

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from £43 /night

£297 - £408 / week

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Late Deal: save up to €96 (approx. £77)

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
In the hills of Tuscany, 3 bedrooms, swimming pool, ideal for family or friends  …see more

22 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £119 /night

£832 - £1200 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Colonica Gigli is a portion of a typical Tuscan farmhouse immersed in the green Chianti hills covered with vineyards and olive groves. Recently restored the original stone building stands in a well tended green lawn.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £143 /night

£1000 - £1480 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Casa Oriolo is an elegant apartment with 3 bedrooms and it is part of a small complex with 3 apartments total sharing a pool. Here you can enjoy a sojourn in contact with nature in a protected and uncontaminated oasis.  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £216 /night

£1512 - £3320 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa.  …see more

24 Photos

Villa | 10 Bedrooms | sleeps 20

7 Nights min stay

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from £629 /night

£4400 - £6240 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
The large 800 sqm villa is an ancient historical residence. Villa Siena, an 18th century villa, rises within a secluded parkland in the hills of Tuscany.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £343 /night

£2400 - £3160 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Villa Nuti is an elegant XVII century manor only 3 km from the center of Siena. From its unique terrace it enjoys privileged magnificent views of the town with its famous bell towers.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £486 /night

£3400 - £4400 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town.  …see more

18 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £138 /night

£960 - £3200 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Demata is the beloved holiday home of a Florentine family with strong American connections as well as a great appreciation for the Tuscan country side and it's pleasures.  …see more

18 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £72 /night

£500 - £1000 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
At only ten minutes' drive from Sinalunga town-centre and yet surrounded by peaceful, unspoilt countryside, this fully restored 17th century Tuscan farmhouse combines the best of both worlds.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £134 /night

£936 - £1920 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
A cypress tree lined road will lead you to Villino le Tortore and it represents a perfect introduction to this amazing Tuscany villa located just 15 minutes walking from Piazza del Campo, the very heart of Siena.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £263 /night

£1840 - £2960 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
The villa is located in a natural reserve and offers walking paths and mountain bike trails, horse riding , historical churches and villas, refreshing dips in the rivers and small lakes.  …see more

16 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £171 /night

£1192 - £1592 / week

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Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
San Donato is an exquisite gem set in rolling Chianti vineyards with views that stretch 360 degrees past a nearby 13th century hill town to Siena and into infinity.  …see more

23 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £480 /night

£3360 - £4480 / 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 Senese is an ancient mansion dating back to the eighteenth century, located in the heart of Chianti Senese, just 17 km away from Siena and 45 Km from Florence.  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £103 /night

£720 - £1992 / week

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Key info:

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

20 Photos

Villa | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £178 /night

£1240 - £1480 / week

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Key info:

  • Nearest beach 130 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Villa Farnetella is an old farmhouse dating back to the XVII century, which has been carefully restored respecting all the traditional architectural characteristics, preserving the stone walls, the original wooden beamed ceilings and the terracotta floors.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

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from £98 /night

£680 - £976 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villino Montisi is a splendid two-story ancient farmhouse surrounded by meadows with breathtaking views over the sweet hills of Tuscany. Recently restored following the architectural Tuscan style with the pale Tuscan stone of the façade.  …see more

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Townhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £100 /night

£700 - £900 / week

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Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
In the very center of a lovely ancient medieval village stands Casa Marelli. Recently carefully restored preserving all the traditional Tuscan characteristics of the building such as wooden beamed ceilings and brick work arches.  …see more

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Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £180 /night

£1260 - £2120 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This compact, two-storey, converted Tuscan farmhouse has been extensively renovated, employing in its restoration solely products certified as ecologically friendly.  …see more