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495 Holiday homes in Siena Province

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Filters applied: High chair (495)

495 Results  |  
20 Photos

Farmhouse | 8 Bedrooms | sleeps 25

Very Good 4.5/5 

Min stay varies throughout the year

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
"The Harvest Moon" holiday house, is a Tuscan country mansion with a spectacular pool overlooking the boundless valley. The whole property is available for more comfort and privacy. The whole property is available for more confort and privacy.  …see more

21 Photos

Farmhouse | 1 Bedroom | sleeps 4

Short stays welcome

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from £58 /night

£400 - £650 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Self catering Farmhouse with 4 luxury apartments in rural Tuscany with swimming pool spectacular views ,nearby golf, walking, trekking, fishing, biking. San Gimignano, and Certaldo, 20 minutes drive, Florence, Siena and Pisa one hour from the house.  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £83 /night

£579 - £620 / 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

Featured properties

17 Photos

House | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £87 /night

£605 - £894 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Belsedere is located on the top of a hill, near Pienza, Montepulciano, Cortona, Monte Oliveto Maggiore, Siena. There are four apartments, which overlook the garden of the villa or the grove of oaks beside the pool. Breakfast included. During the high season we offer a Sunday evening dinner guests of the farm.  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £29 /night

£202 - £430 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
The apartment "La Tognazzina" is 42 mq. and it's situated at the first floor of an ancient building from the beginning of '900. it is few minutes drive from Siena.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £282 /night

£1972 - £2891 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Lovely villa, South of Siena, perfect base for the exploration of Tuscany. Private pool, isolated, complete privacy. Ideal for families or groups: rates for 7, 12 and - adding a small apartment - 16people (price on request). Children and pets are welcome.  …see more

24 Photos

B&B | 7 Bedrooms | sleeps 19

1 night min stay

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from £465 /night

£3251 - £4170 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Antico Granaione B&B has 7 rooms with private bathroom,(max guests 19) a main hall equipped with a professional kitchen, reserved to our buffet breakfast, banquets, special events, a relax area to read, play piano. Cooking classes are held by Patrizia Cencioni, licensed master chef at A.I.CI.  …see more

19 Photos

Castle | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £53 /night

£368 - £1139 / week

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Key info:

  • Nearest beach 75 km
  • Suitable for over 5s only
  • Car advised
  • Pets welcome
  • Private garden
Holidays in an original Castle near Siena! Castello di Capria offers the perfect location for history and nature loving guests. Space for up to 10 people in comfortable rooms, self catered or with catering. Special Getaway for smaller groups for up to 10 people. Golf nearby, Horse riding nearby, swimming nearby.  …see more

16 Photos

Farmhouse | 6 Bedrooms | sleeps 20

Excellent 5/5 

2 Nights min stay

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from £526 /night

£3680 - £5081 / 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

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 | 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

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

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

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

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

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

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

6 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Min stay varies throughout the year

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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

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

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

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

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

23 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Min stay varies throughout the year

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from £88 /night

£614 - £1402 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
CHIANTI , WINE , COOKING CLASS , AGRITURISMO , LANDSCAPE , VIEW  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

3 Nights min stay

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from £69 /night

£482 - £701 / week

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Key info:

  • Nearest beach 55 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Self-catering apartment, very comfortable, three bedrooms, a large living with two comfortable armchairs, and an open well furnished kitchen. Located in a wonderful Tuscan countryside, surrounded by a very large garden and a new pool. Ideal for families.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £99 /night

£690 - £868 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This Tuscan 17th century farmhouse with 2 bedrooms, Villa Arpicella, is located very close to Pienza and it enjoys the stunning countryside setting with spectacular wide open views.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £142 /night

£992 - £1612 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Immersed in the green countryside on the outskirts of Siena, Villa Palio offers all the quiet of its natural setting just a stone throw from the very center of the town of Siena.  …see more

19 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £473 /night

£3306 - £4959 / 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 Corte is a large farmhouse from the early 15th century, built around a thousand-year-old lookout Lombard tower and set inside six hectares of private grounds amidst the hills covered in vineyards and olive trees, just outside of San Gimignano.  …see more

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £414 /night

£2893 - £3926 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Oliveto is the guest villa, and sits at the end of an olive grove known for producing one of Italy's premier extra virgin olive oils. The villa, the pool & the gardens are totally private - separated from the main house by a large expanse of olive grove.  …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

24 Photos

Apartment | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £148 /night

£1034 - £1529 / 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

15 Photos

Townhouse | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £104 /night

£724 - £930 / 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

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

18 Photos

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

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £224 /night

£1562 - £3430 / 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

20 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £142 /night

£992 - £1653 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
It is the most photographed house in the area, a symbol of the Tuscany countryside, featured on many postcards and calendars simply because it has maintained the charm of the old farmhouse and the surrounding fields, without any new buildings as far as the eye can see.  …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 | 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

Fort | 1 Bedroom | sleeps 3

3 Nights min stay

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from £108 /night

£751 - £834 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • 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

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

24 Photos

Villa | 5 Bedrooms | sleeps 8

7 Nights min stay

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from £473 /night

£3306 - £5372 / 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
This comfortable, cosy villa nestles on a sheltered incline among gently rolling hills. These are covered in Brunello wine-producing vineyards, which border the lower pool-terrace. The San Giuseppe winery, from which the house takes its name, is situated nearby.  …see more

22 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £271 /night

£1894 - £2581 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Magical Tuscan farmhouse with pool overlooking the stunning Siena countryside. Enjoying the most beautiful and tranquil of settings Le Contessine offers both a relaxing escape and a strategic location for touring the whole of Tuscany and Umbria with ease. 4 bedrooms.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £178 /night

£1240 - £1984 / 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

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

11 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

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from £88 /night

£614 - £859 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
We have 5 independent self catering apartments and 2 double rooms with private bathrooms. The apartments have their own kitchenettes inc. oven, fridge and gas hobs. Swimming pool, gardens, outdoor wood oven and BBQ are free to all our guests. We have a restaurant 2 km's from the farmhouse offering tuscan cuisine & Pizza with an outdoor terrace.  …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

11 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £107 /night

£745 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
In Podere Malabiccia all the rooms enjoy views of the surrounding landscape. Sunroom with west-facing arced windows. Kitchen with a large fireplace and antique wood burning oven. Living room and informal dining room with a fireplace. Antique Tuscan ceramics. Garden.  …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

11 Photos

House | 2 Bedrooms | sleeps 7

3 Nights min stay

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from £62 /night

£430 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Extraordinary typical tuscan historic eighteenth-century residence, all restored, all high standard confort, located on a hilltop in the Siena countryside, in the charming medieval village Sinalunga. You will love your holidays there! Come and live the tuscan way of life : relaxing, friendly, refined.  …see more

23 Photos

Fort | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £155 /night

£1085 - £1185 / 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