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1,762 Results  |  
17 Photos

Apartment | 2 Bedrooms | sleeps 5

Short stays welcome

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from £108 /night

£751 - £1085 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Central elegant apartment, tastefully furnished, large entrance with sitting area, dining area, equipped kitchen, bedroom with double bed, twin bedded bedroom, a bathroom with shower, a bathroom with tub/shower, WIFI, TV, (air conditioning upon request is paid apart) Sail with us on board of Free Will to the Tuscan Archipelago, Sardinia, Corsica.  …see more

7 Photos

Apartment | 1 Bedroom | sleeps 5

Excellent 5/5 

3 Nights min stay

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from £78 /night

£543 - £792 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Red Apartment (3+2 pax) Via del Romitorio, 3 Central, located at ground floor, easily accessible, perfect for a family, cosy, light, tastefully furnished. Living area with sofa bed, kichenette, triple bedroom, bathroom with shower, WIFI, Sat Tv, airconditioning. Sail with us on board of Free Will to the Tuscan Archipelago, Sardinia, Corsica.  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £66 /night

£459 - £667 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
GREEN APARTMENT (2+2 pax) Via del Romitorio, 3 Central, ground floor, easy accessible, light, cosy, tastefully furnished. Double bedroom, fully equipped kitchen with sofa bed for two guests, large bathroom with shower, WIFI, sat Tv, airconditioning. Sail with us on board of Free Will to the Tuscan Archipelago, Sardinia, Corsica.  …see more

Featured properties

21 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £213 /night

£1490 - £1928 / 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
Self -Catering Tuscan farmhouse with 4 large bedrooms in a cozy hamlet immersed in the rolling hills of Tuscany. Lovely shared pool. Al-fresco private garden dining and stunning views of the surrounding countryside. Perfect for families with children! Cooking classes. The Pheasant farmhouse is the original house of the this antique hamlet surrounded by rolling Tuscan hills.  …see more

23 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £126 /night

£877 - £1131 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
A fabulously romantic stone farmhouse with its own private garden and shared pool. Ideal for a family of 4 or 2 couples looking for peace and tranquility.Proximity to Siena (very easy 30 min drive), Montalcino and the wine region. Wine tastings offered onsite. Exclusive renovated hay loft with private garden, aircon and sweeping views of the surrounding Orcia valley.  …see more

24 Photos

Farmhouse | 10 Bedrooms | sleeps 20

Short stays welcome

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from £526 /night

£3680 / 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 that compose an antique Borgo with a shared pool overlooking the gorgeous countryside. Each farmhouse is unique, and varies in size from 2 to 4 bedrooms. Ideal for families, weddings and family reunions. You haven't seen the real Tuscany until you see the Val d'Orcia. Wine tastings and cooking classes on site.  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

3 Nights min stay

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from £138 /night

£964 - £1972 / 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
Spaciously comfortable farmhouse with country antiques immersed in the unique Orcia valley hillside. 4 bedrooms with 2 large bathrooms. Great for families. Enjoy your meals under the outdoor covered eating area overlooking the hillside scenery. Cooking classes available This spacious apartment in its own farmhouse is rentable for a group of 4 or 8 persons.  …see more

20 Photos

Farmhouse | 1 Bedroom | sleeps 3

3 Nights min stay

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from £123 /night

£859 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Apartment located inside an Agriturismo in Montepulciano Tuscany. The apartment has a double room, a kitchen, a dining room with Fireplace and a private batrhoom with Jacuzzi. Available to clients: Private Parking, Gazebo and Swimming Pool.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £501 /night

£3505 - £4672 / week

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Key info:

  • Nearest beach 74 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

13 Photos

B&B | 11 Bedrooms | sleeps 24

3 Nights min stay

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from £87 /night

£608 - £7322 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Romantic location surrounded by olive trees and vineyards Beauiful B&B near San Gimignano in the heart of Tuscany New comfortable rooms Rich breakfast buffet on the terrace Large swimming pool with loungers Free parking Olive oil and precious wines from home production  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £101 /night

£701 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Situated on the hills of Val di Chiana, La Giuda country farm offers an ancient stable, completely restored and furnished, divisible in three apartments in a comfortable and friendly atmosphere. Guest can taste the delicious meals prepared with the products of the farm The farm produces organic Chianti classico vine and olive oil  …see more

7 Photos

Apartment | 1 Bedroom | sleeps 4

2 Nights min stay

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from £82 /night

£570 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • No pets allowed
  • Private garden
The place is in a strategic position, very nice and peacefully. the atmosphere is familiar and unique. you can eat with the owners and enjoy home made food and organic product of the farm  …see more

8 Photos

Apartment | 1 Bedroom | sleeps 2

Min stay varies

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from £88 /night

£614 / week

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Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Panoramic view on Pienza and the Val d'Orcia. Monticchiello os a pretty medieval village in the heart of the Val d'Orcia  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £201 /night

£1402 - £2191 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Colletalli is an ideal location to recharge ones energy away from the humdrum of daily life conveniently located within 1 hour motoring of Florence, Siena, Sangimignano, Volterra, sandy beaches  …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

9 Photos

Studio | sleeps 4

Min stay varies

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from £57 /night

£395 / week

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Key info:

  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
The street is one of the most important in Siena, 2 minutes to il " Campo" and all monuments and museums. The area is for pedestrians, only 300 metres to the bus terminal, 1 hour from Florence, 3 hours from Rome. In front of the house, a charming XV° century church. Rent is 450 euro pw (all included ), less for a long stay. The minimum length of stay is 3 days (300 euro).  …see more

14 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £82 /night

£570 - £701 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Typical house in the heart of Siena's countryside,suitable for vacations from Spring to late October; come and discover the true pleasure of a vacation in Tuscany -150 euro damage deposit to be paid cash upon arrival -Internet conn. on request 6€ per 3GB or 20€ for 10GB  …see more

6 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

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from £57 /night

£395 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
A family atmosphere an the possibility to eat with the owners, tasting home made food prepared with organic products of the farm. Silence and peacefully athmosphere.  …see more

24 Photos

Cottage | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £66 /night

£460 - £920 / week

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Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
A beautiful farm where you can relax on the porch with a good book and a glass of Chianti or walking on the grass in the magnificent park of oak trees, it is also an excellent base for exploring the heart of Tuscany, between Siena and Florence.  …see more

12 Photos

Guest house | 1 Bedroom | sleeps 2

3 Nights min stay

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from £87 /night

£608 - £767 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Romantic guest house with swimming pool in the midst of nature just 1km away from San Gimignano. Tuscany highlights such as the Uffizi Gallery in Florence, the Leaning Tower of Pisa and the enchanting Piazza del Campo in Siena are all close at hands. Its strategic position makes San Gimignano the ideal starting point for day excursions throughout Tuscany.  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £44 /night

£307 - £377 / week

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Key info:

  • Nearest beach 60 km
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
This apartment is in the historical center of a beautiful town near Siena. Its name is Monticiano. It's composed by 2 bedrooms (for 4 gests), 1 bathroom (with a shower box), 1 indipendent kitchen and a great dining room. The apartment is 75 mq.  …see more

18 Photos

Cottage | 2 Bedrooms | sleeps 4

1 night min stay

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from £92 /night

£640 / week

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Key info:

  • Nearest beach 50 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Beautiful cottage with garden on the grounds of the Castle of Grotti, 12km south of Siena. Amazing views over the Crete and the Val d'Orcia. Ideal base. Perfect for a relaxing and romantic holiday in Tuscany.  …see more

6 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Min stay varies

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from £152 /night

£1060 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
Nestled at the top of a hill in a peacfuly location with breaktaking views. The property is beautifully landscaped and has spacious rooms with an open plan kitchen morden interior look with geothermal heating and cooling system.  …see more

20 Photos

Farmhouse | 5 Bedrooms | sleeps 9

3 Nights min stay

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from £128 /night

£893 - £1686 / 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

19 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £231 /night

£1612 - £3100 / 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

21 Photos

Castle | 6 Bedrooms | sleeps 16

4 Nights min stay

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from £390 /night

£2728 - £3182 / 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

23 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £213 /night

£1488 - £2976 / 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 £355 /night

£2480 - £3720 / 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

18 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

5 Nights min stay

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from £81 /night

£565 - £850 / week

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Key info:

  • Nearest beach 66 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Holiday apartment with shared pool. Its rural position offers complete relaxation and a wonderful panoramic view. Near Volterra and San Gimignano, it's a perfect base to visit Florence, Pisa and Siena. Perfect for families and couples. The area boasts some of the best views Tuscany has the offer, the entire area being a national park.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £51 /night

£356 / week

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Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Lovely villa apartment overlooking the Tuscany hills, stunning views over the hills. 20 minutes away from Siena, 50 minutes away from Florence, central location. Full comfort, garden and pool. Typical Tuscan architecture (ogive arches) and decoration. Private outdoor veranda with garden furniture.  …see more

5 Photos

Apartment | 2 Bedrooms | sleeps 3

Min stay varies

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from £38 /night

£263 - £351 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Agriturismo Raggio di Sole is about few meters from the city of Montepulciano, famous all over the world for the Vino Nobile and rich in artistical and cultural events: Cantiere Internazionale d'Arte, Bruscello, Bravìo etc..  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £218 /night

£1526 - £2064 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
A typical stone barn immersed in the Tuscan countryside of San Gimignano. A large garden overlooks the hills and surrounding countryside. Up to 7 people in a both modern and rustic atmosphere.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

Excellent 5/5 

7 Nights min stay

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from £555 /night

£3885 - £6529 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
This spacious, stylishly furnished villa is set in extensive grounds, which offer a choice of venues for outdoor relaxation and dining. It is tucked away in a very secluded spot, amid gently rolling wooded hills.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 16

7 Nights min stay

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from £517 /night

£3616 - £5682 / 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
Villa San Biagio is situated close to Montepulciano. This magnificent country house is known for being the most exclusive and stunning farmhouse you can find in this area. It is the perfect choice if you are looking for a peaceful and relaxing holiday.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £355 /night

£2480 - £3265 / 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
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 | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £549 /night

£3843 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Everything about this property is classically Tuscan. Misty hills covered in precision lines of vineyards, olive groves, gravel roads and driveways shadily lined with pointy cypress trees, and grand villas with green shutters.  …see more

18 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £74 /night

£517 - £1034 / 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 | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £591 /night

£4133 - £4546 / week

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Key info:

  • 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

22 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £123 /night

£860 - £1240 / 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

Villa | 10 Bedrooms | sleeps 20

7 Nights min stay

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from £650 /night

£4546 - £6447 / 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 | 8 Bedrooms | sleeps 16

7 Nights min stay

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from £473 /night

£3306 - £4877 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Villa La Torre is a medieval lookout tower, built more than 8 centuries ago on Etruscan foundations, and at a later date incorporated into the farmhouse structure.  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 19

7 Nights min stay

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from £296 /night

£2067 - £5290 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights 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
This elegant villa, with cream-washed external walls, dates back to the late 16th century, when it served as the summer residence and hunting lodge of the noble Tolomei family.  …see more

22 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £178 /night

£1240 - £2315 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Filippo, is a delicious apartment and it is part of a farmhouse divided in 3 units located close to Montalcino. This apartment can accommodate 6 persons in 3 bedrooms and 2 bathrooms.  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £207 /night

£1447 - £2191 / 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

18 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £225 /night

£1571 - £2315 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Il Maggio is a typical 18th century Tuscan hill house. The villa offers all modern conveniences and some very particular details including a carefully designed and comfortably furnished solarium with large heated spa bath, a few steps from the house.  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £107 /night

£744 - £2058 / 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

22 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £124 /night

£868 - £1240 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
This little, two-storey, converted Tuscany farmhouse has been meticulously restored in a simple, rustic style, employing high-quality traditional materials.  …see more

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Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £142 /night

£992 - £3306 / 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

4 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £642 /night

£4490 - £6352 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
A beautiful villa recently restored with an absolutely fascinating panoramic position; surrounded by Mediterranean vegetation and of vines and olives  …see more