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22 Photos

Apartment | 1 Bedroom | sleeps 2

Good 3/5 

1 night min stay

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from £53 /night

£368 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Ideal romantic nest house in the middle of luscious green Tuscan countryside with superb views and possibility of outdoor life. Suìtable in all seasons aqs the basis for visiting Siena Florence and all the nearby historical Tuscan sites.  …see more

20 Photos

House | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £41 /night

£281 - £456 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Sun in summer, snow in winter, hiking, culture and charm of nature nothing is missing for a wonderful holiday in the comfortable house Contignano. The price is guaranteed. There are no additional charges. Utilities are included in the price.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £38 /night

£263 - £439 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
we rent house in center of Montepulciano. Flat (apartment) of roughly 60 sq m (646 sq ft), located in via Cagnano 9. Restored in 2011 it is has high quality finishes and exposed beams. It consists of a large living room/kitchen, two bedrooms (one of which is a master b  …see more

Featured properties

20 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £38 /night

£265 - £742 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
With beautiful views over the village, this ground floor, comfortable apartment is the perfect spot! Modern facilities including a Swimming pool a gym, and table tennis. The apartment has 2 bedrooms, a well equipped kitchen, a dining terrace, and underground parking. The multinational users are generally quiet and friendly, respectful of the natural ambience of the Borgo.  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £118 /night

£820 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
On the sweet hills of the Chianti shire between vineyardand and olive groves, stands the "Podere il Pino". It offers a spectacular view on the beautiful medieval village of San Gimignano and it is very close to art cities as Florence, Siena, Pisa, Volterra and the sea.  …see more

20 Photos

Farmhouse | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £103 /night

£716 - £1060 / week

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Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Spectacular Views! Well equipped apartment in great location.Great for families. Outside, is a very attractive pergola, with BBQ for drinks and meals, overlooking the beautiful Tuscan hills and valleys. Vouchers for the local spa are provided upon request. Logs for the fire are provided free of charge.  …see more

18 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

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from £137 /night

£955 - £1831 / week

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Key info:

  • Nearest beach 50 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

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £70 /night

£490 - £690 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A spacious 1 bed apartment with garden and bbq terrace, in a picturesque setting, only a short walk to local services. Enjoy free use of cycles & gym or just relax by the pool. Launderette & internet services add home comforts and a glass of wine greets you on arrival. Minore is ideally situated to enjoy the areas premier events including Siena Palio & Gaiole Eroica.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

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from £71 /night

£491 - £614 / 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
A 2 rooms apartment, with a double/twin bedroom, large bathroom with shower and jacuzzi bathtub, large sitting room with a double sofa bed, dining area with kitchen corner, fully furnished with oven. Chimney, satellite tv, wifi. salty water swimming pool.  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

1 night min stay

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from £69 /night

£482 - £1577 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Wonderful place to relax, make sports ( walking,archery and swimming) sip our good wine and enjoy our cousine. Our swimming pool is 15x5mt wide and is cleaned using salt and not chlorine.  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £99 /night

£687 - £1196 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Comfortabel two bedroomed, two bathroom apartment in a lovely traditional country villa near San Gimignano. Large garden, swimming pool, free parking on the property 24 hour help for guests as the owner lives on the property. Shops / train 4 km from the villa Great position from which to explore Tuscany. Transport, restaurants, supermarkets 4 km  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £172 /night

£1200 - £1500 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A bright roomy south facing 3 bed/2 bath apartment with panaramic views over Gaiole and the hills beyond. Enjoy al fresco dining on the terrace or doze in a wisteria shaded hammock. Relax by the pool, take a cycle ride or just stroll down to the village restuarants. Maggiore is ideally situated to enjoy the areas premier events including Siena Palio and Gaiole Eroica.  …see more

24 Photos

Farmhouse | 7 Bedrooms | sleeps 16

Very Good 4.5/5 

1 night min stay

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from £63 /night

£439 - £4030 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Swimming pool 15x5mt, cleaned using salt not chlorine. 3D archery range with wild animal targets, bow rental and trainer available. Try Alessandro's traditional cousine, it will surprise you! Our cellar and vineyards are open for visit, taste our Rosso di Montepulciano  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £106 /night

£736 - £1227 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Girasole is one of 4 apartments in our family Villa. It is very centrally situated so that guests can discover the major treasures of Tuscany in half or whole day trips. Over the last 30 years our family has offered a personal, caring hospitality and guests have often returned  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £182 /night

£1271 - £1621 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
The villa is 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 cities of Siena and Florence.  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 5

Very Good 4/5 

1 night min stay

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from £41 /night

£281 - £684 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
A few minutes' walk from Siena centre and Railway Station, this welcoming apartment overlooks the Tuscan hills. It is perfect for travelers looking to visit Siena and surrounding medieval towns and markets. Great for couples or single travelers.  …see more

24 Photos

Apartment | 4 Bedrooms | sleeps 12

Excellent 5/5 

4 Nights min stay

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from £229 /night

£1600 - £2000 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A spacious townhouse complex on two levels well suited to sharing families in easy strolling distance of restaurants, delicatessens, bars etc; large pool, gym, free bicycle hire and plenty of private outdoor space with lovely views offers something for all the family.  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £99 /night

£687 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Gelsomino is one of 4 apartments in our family Villa. It is very centrally situated so that guests can discover the major treasures of Tuscany in half or whole day trips. Over the last 30 years our family has offered a personal, caring hospitality and guests have often returned  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 8

3 Nights min stay

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from £90 /night

£626 - £687 / week

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Key info:

  • Nearest beach 90 km
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Large, elegant, comfortable apartment in incomparable surroundings. Peaceful and relaxing with spectacular scenery. 3 km from Castellina in Chianti with its medieval town centre, shops, bars, restaurants. 22 km from Siena., 37km from Florence. No neighbours or noise. Perfect to come home to after the day's excursions. A glass of wine in the garden, dinner under the stars.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £79 /night

£552 - £675 / 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
In the middle of the Siena hills facing the Cecina valley, Ulivo is situated within the villa of Il Bel Canto at a short distance from Volterra, San Gimignano, Siena & the sea coast. Ideal for relacing and enjoying the beautiful 360 degrees view.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

5 Nights min stay

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from £470 /night

£3290 - £3965 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Sleeps 14 with possibility to add adjacent apartments up to total of 33. A beautiful 15th-century villa in the heart of the Chianti countryside, with 360° uninterrupted views of olives, vines and forests, with amazing sunset views over San Gimignano and the Apennines  …see more

20 Photos

Villa | 11 Bedrooms | sleeps 26

2 Nights min stay

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from £71 /night

£491 - £5958 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
On the ground floor there are large rooms, with fireplaces, which lead outside to a semi-circular parterre-solarium paved in terracotta.On the first floor there are 8 double rooms all with private bathrooms with shower, more rooms in the lemon house On the ground floor there's a double room with private bathroom with access to the swimming pool  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 5

5 Nights min stay

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from £156 /night

£1087 - £1433 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Le Stalle is a lovely 2-bedroom apartment situated on the ground floor of Podere Patrignone, a 15th century farmhouse in the heart of Chianti, surrounded on all sides by olives, vines, hills and forest. It has a kitchen, dining area, outside porch and use of the pool.  …see more

18 Photos

Apartment | 1 Bedroom | sleeps 4

Very Good 4/5 

7 Nights min stay

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from £37 /night

£255 - £307 / week

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Late Deal: save up to €80 (approx. £66)

Key info:

  • Nearest beach 120 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
House with character, near 'Parco delle piscine', ideal to visit Tuscany and Umbria.  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £39 /night

£272 - £526 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

3 Nights min stay

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from £188 /night

£1315 - £2191 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This enchanting holiday home is on a knoll overlooking the typical Tuscan countryside of the area around Pienza, San Quirico and Montalcino. In a very quiet position, only surrounded by a peaceful Tuscan countryside, this holiday accommodation consists of 4 apartments  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £32 /night

£220 - £439 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
nice and comfortable apartments in walking distance from the village .  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £56 /night

£386 - £482 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Siena apartment with easy access to the town centre  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £41 /night

£281 - £526 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 5

7 Nights min stay

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from £44 /night

£303 - £570 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £32 /night

£220 - £439 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
nice and comfortable apartments in walking distance from the village  …see more

16 Photos

Farmhouse | 1 Bedroom | sleeps 3

7 Nights min stay

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from £34 /night

£237 - £469 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

22 Photos

Tower | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £162 /night

£1131 - £2243 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • May take pets – please enquire
  • Private garden
Stunning medieval tower near San Gimignano for holiday rentals  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

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from £226 /night

£1577 - £2979 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
This beautiful villa in Siena is situated on the hills with a breathtaking view over the vineyards up to Siena. An ideal accommodation for all those seeking peace and quiet but also a perfect point of departure for visiting the beautiful attractions of the Chianti  …see more

22 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £47 /night

£325 - £658 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 7

Very Good 4/5 

3 Nights min stay

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from £84 /night

£587 - £1017 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Gorgeous holiday villa in Siena, just 5 minutes walking from the town. blloming garden, shared swimming pool, private car parking, internet (with flash drive), laundry room, chef for dinner or meal on request  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £261 /night

£1823 - £4643 / 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
Splendid villa with breathtaking view over the Castle of Strozzavolta, in the Chianti, between Florence and Siena.  …see more

16 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £69 /night

£482 - £728 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is furnished tastefully and with exclusive period furniture, fireplace, Sky TV, independent heating, external private space. Park, scenic swimming pool.  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 4

1 night min stay

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from £59 /night

£409 - £584 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Farmhouse apartment with seasonal outdoor pool, in Montepulciano Tuscany country estate surrounded with the wonderful Nobile-Vineyards.  …see more

19 Photos

House | 15 Bedrooms | sleeps 30

Min stay varies

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
Poggiarello is a special place to spend a charming holiday in close contact with nature, where is possible to reach in few minutes Siena, San Gimignano, Firenze, Pisa, Lucca, Monteriggioni,Montalcino.  …see more

19 Photos

Farmhouse | 12 Bedrooms | sleeps 30

1 night min stay

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from £36 /night

£246 - £10119 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Our estate is composed of well equipped units: apartments with cooking corner, completely restored in typical tuscan style, maintaining intact the old original elements such as wooden-beam and arched ceilings, brickwork floors. Each unit disposes of private entrance A wide range of services and activities: walkings, ridings, excursions by byke, photo-tours, cooking-classes  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 7

6 Nights min stay

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from £148 /night

£1034 - £2164 / week

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Late Deal: save up to €746 (approx. £617)

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
Charming Chianti villa, Siena 6 km far away, with different prices from 4 to 7 persons, fantastic pool (12x6 meters), terrace with pergola and stunning view on the countryside. Ideal position to visit the most important towns of the Chianti and Val d'Orcia areas, like Castellina in Ch  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 11

5 Nights min stay

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from £248 /night

£1735 - £3715 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Basciano. The house position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena.  …see more

16 Photos

Barn | 1 Bedroom | sleeps 3

5 Nights min stay

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from £58 /night

£405 - £951 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The property location allows a pleasant vacation in the countryside, and is a good point of reference for visiting Siena (5 miles).  …see more

11 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

Min stay varies

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Key info:

  • Nearest beach 62 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
L fienile di Colletalli is an ancient barn restored and converted into the most beautiful and unique spa resort. Is just five minutes by car from middle-age village Radicondoli. A large living room, a private and exclusive beautiful farm, a terrace, a garden, and a pool  …see more

8 Photos

Apartment | 1 Bedroom | sleeps 5

1 night min stay

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from £10 /night

£70 - £525 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Situated in the heart of tuscany (hills, between volterra, famous etruscan and medieval city and san gimignano, famous all over the world for its characteristic towers. You can easily visit florence, siena and pisa, chianti region, thyrrenian sea, monteriggioni. Charac  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

1 night min stay

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from £113 /night

£789 - £1139 / 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 Zafferano, ideal for a self catering holiday, is found in the hamlet of Vergelle, set amongst the peaceful countryside known as the Crete Senesi, south of Siena, in Tuscany. It is close to the hilltop town Montalcino with its world famous Brunello vineyards. This large 4 bedroomed villa is part of Vergelle’s old school building, and was fully renovated in 2008.  …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

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Villa | 3 Bedrooms | sleeps 6

Short stays welcome

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from £149 /night

£1043 - £1831 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

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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