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107 Results  |  
23 Photos

Apartment | 3 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £143 /night

£1000 - £1500 / week

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Key info:

  • Swimming pool
  • Great 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

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £75 /night

£523 - £896 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Chianti farmhouse, Gaiole in Chianti, pool, Barn, Gite, Demeure de charme, piscine, cités d'art, barn, la casa in chianti, Casa Forcheri Fico for 6 people Cipresso for 4/5 p Olivo for 4-6 p Cipresso+Olivo, maximum 11p  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £75 /night

£525 - £725 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great 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

Featured properties

19 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

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from £536 /night

£3751 - £5762 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
This beautiful, rustic villa is built on the side of a hill and surrounded by vineyards and woods. The villa is at the heart of an agricultural estate that produces organic wine and extra virgin olive oil. Good food, wine and relaxation await you in the heart of Tuscany  …see more

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £202 /night

£1411 - £3098 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £72 /night

£504 - £743 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
A fantastic apartment, 2 bedrooms, 2 bathrooms and livingroom/kitchen. The apartment is one of the towers in beautiful Borgo Gaoile. From the livingroom/kitchen there is a wonderful view over Gaiole and the valley. The wall in the living/kitchen is a glasfoldingdoor. You can open the whole wall in the livingroom/kitchen and make an "out side room" - and what a view.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

Very Good 4/5 

7 Nights min stay

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from £67 /night

£463 - £848 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
This well positioned house has gardens to the South and East and enjoys a sunny aspect from sun rise to sun set, the house has a high quality finish in the old Tuscan style and has superb views all around of pine forest, vineyards and olive groves.  …see more

24 Photos

Apartment | 4 Bedrooms | sleeps 12

Excellent 5/5 

4 Nights min stay

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from £229 /night

£1600 - £2100 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great 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

20 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £176 /night

£1232 - £2053 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
La Fontanella is fantastically located in the heart of the Chianti, just on the edge of a quaint stone village filled with Tuscan character and charm. Several of the main Chianti vineyards can easily be reached for wine tastings, these include Brolio, Dievole and Meleto  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

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from £320 /night

£2236 - £4120 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Private Villa with pool in Gaiole in Chianti in Tuscany sleeping up to 12 people with 5 beds 5 baths in main house and a barn conversion with a separate one bedroomed apartment in the grounds. A great property for large families or groups travelling together.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

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from £76 /night

£530 - £1209 / week

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Key info:

  • Nearest beach 107 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Located within walking distance of the village of Gaiole in Chianti, the villa offers the perfect setting to explore the Chianti Classico region, enjoy the breathtaking views of the vineyards and olive groves, and experience the charming Tuscan lifestyle. Beautiful villa located within walking distance of the village of Gaiole in Chianti, near Siena, Tuscany  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £156 /night

£1086 - £1809 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in San Sano with 3 bedrooms sleeps 8  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

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from £140 /night

£980 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Diora E is a characteristic and welcoming independent house surrounded by vineyards and olive groves. It sleeps six people. From Villa Diora E you will enjoy an enchanting view of the Tuscan hills and of the Chianti valley  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £195 /night

£1361 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole -Apartment Yardandnbsp;is a rental holiday apartment inandnbsp;Gaiole, Chianti, in the province of Siena, Tuscany . The Chianti area is spread across the provinces of Florence and Siena and includes the municipalities ofandnbsp;Greve, Panzano, Radda, Gaiole and  …see more

16 Photos

Farmhouse | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £552 /night

£3859 - £5672 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

22 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Min stay varies

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Pricing unknown

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Le Diacce, an enchanting 18th century old farmhouse, belonging to Podere Ciona, 40 hectares of vineyards and woodland, enjoys a unique view on the surrounding hills covered with vineyards, olive groves and woods with Siena in the far distance.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £476 /night

£3330 - £4798 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Villa Stefano dates back to the 10th century and was originally a traditional stone water mill. With all the comforts of a modern villa, many of the original features including meter thick walls, wood beamed and tiled ceilings, and cotto floors still remain.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £55 /night

£385 - £698 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children over 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany. Gaiole is in the Chianti Classico area, ideal to taste and enjoy the best wines and olive oil in Italy.  …see more

20 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £143 /night

£998 - £1425 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £72 /night

£504 - £640 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £64 /night

£448 - £580 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

20 Photos

House | 4 Bedrooms | sleeps 7

1 night min stay

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from £550 /night

£3850 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Diora A is a splendid sixteenth-century two-story apartment that is part of a villa situated in the heart of the Tuscan countryside. It sleeps seven people. From Villa Diora A you will enjoy an enchanting view of the Chianti hills and of the vineyards  …see more

16 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £310 /night

£2165 - £3396 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Selvole with 3 bedrooms sleeps 6  …see more

8 Photos

Apartment | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £274 /night

£1915 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole-Apartment Nestandnbsp;is a striking countryside apartment inandnbsp;Gaiole in Chianti, a municipality in Siena, Tuscany 'Forbes', a reputed American magazine, rates Gaiole in Chianti as "Europe's . Theandnbsp;Chianti Classico wineandnbsp;region is situated to  …see more

8 Photos

Apartment | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £195 /night

£1361 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Theandnbsp;Apartmentandnbsp;can comfortably accommodateandnbsp;4andnbsp;people.andnbsp; It is situated on theandnbsp;ground floorandnbsp;with splendid panorama. There is a well furnishedandnbsp;living room,andnbsp;kitchen-dining room, aandnbsp;double bed  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

5 Nights min stay

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from £173 /night

£1209 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartment Wavesandnbsp;is provided withandnbsp;private terrace, air conditioning, panoramic living roomandnbsp;with open fireplace, aandnbsp;fully furnished kitchen and dining room, a double bedroomandnbsp;withandnbsp;queen size bed, beautifully tiled bathroom with  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £69 /night

£479 - £607 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £97 /night

£673 - £821 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 2 bedrooms sleeps 4  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £117 /night

£815 - £1065 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 3 bedrooms sleeps 5  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £109 /night

£761 - £1045 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £143 /night

£998 - £1425 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £193 /night

£1349 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Tuscan Sunandnbsp;is a holiday villa in Tuscany, in the municipality of Gaiole, in Siena. With an outdoor swimming pool and antique furnishing, the villa is ideal for an Italian vacation. Villa Tuscan Sun is situated on the green sloping hills of Siena, offering  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £325 /night

£2274 - £3410 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 4 bedrooms sleeps 8  …see more

12 Photos

Apartment | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £274 /night

£1915 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole-Apartment Ventoandnbsp;is a andnbsp;threeandnbsp;bedroom rental countryside apartment in the hamlet of Gaiole in theandnbsp;Chianti region of Siena, Tuscany. San Gimignano, a small walled hill town in the province of Siena, is famous for itsandnbsp;medieval  …see more

9 Photos

B&B | 1 Bedroom | sleeps 2

5 Nights min stay

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from £173 /night

£1209 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartmentandnbsp;Barnandnbsp;is located in splendid Chianti country side on the ground floor, can comfortably accommodate andnbsp;twoandnbsp;people.andnbsp; There is aandnbsp;double bed roomandnbsp;with open fireplace,andnbsp;small kitchen, bath room with hydro  …see more

17 Photos

Farmhouse | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £497 /night

£3478 - £5963 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Modern design combined to the original structure. Modern facilities including air conditioning. Very peaceful and secluded position in the Chianti region. Optional guest house.  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £143 /night

£998 - £1425 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

22 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £109 /night

£761 - £1045 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £200 /night

£1395 - £1848 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Lecchi with 5 bedrooms sleeps 10  …see more

24 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £69 /night

£479 - £607 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

8 Photos

B&B | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £173 /night

£1209 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartment Archesandnbsp;is ideally located inandnbsp;Chianti countryside. It is on theandnbsp;ground floor, aboutandnbsp;80 m2, can comfortably sleepandnbsp;3andnbsp;people.andnbsp; There is aandnbsp;living roomandnbsp;with open fireplace,andnbsp;dining room,  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

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from £140 /night

£980 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Diora B is a characteristic and welcoming apartment that is part of a villa surrounded by vineyards and olive groves. It sleeps six people. From Villa Diora B you will enjoy an enchanting view of the Tuscan hills and of the Chianti valley  …see more

20 Photos

House | 4 Bedrooms | sleeps 7

1 night min stay

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from £426 /night

£2980 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Diora F is a splendid sixteenth-century apartment that is part of a villa in the characteristic style of the Tuscan countryside. It sleeps seven people. From Villa Diora F you will enjoy an enchanting view of the Chianti hills and of the vineyards  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £600 /night

£4198 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Enrichettaandnbsp;is located in a charming medieval hamlet set in one of the most idyllic Tuscan scenery, surrounded by gently rolling, green hills and vineyards. The villa in authentic Chianti style is linear, luminous, almost a sculpture built onandnbsp;three  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £129 /night

£900 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Diora D is a characteristic and welcoming independent house surrounded by vineyards and olive groves. It sleeps four people. From Villa Diora D you will enjoy an enchanting view of the Tuscan hills and of the Chianti valley  …see more

15 Photos

Farmhouse | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £456 /night

£3187 - £4680 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

16 Photos

Farmhouse | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £638 /night

£4463 - £6657 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

20 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £102 /night

£713 - £998 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

8 Photos

Apartment | 4 Bedrooms | sleeps 6

5 Nights min stay

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from £274 /night

£1915 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole-Apartment Canopyandnbsp;is a Tuscany rental in the municipality ofandnbsp;Gaiole, Chianti, in Siena, Tuscany. Gaiole in Chianti is a striking little township and rated as one of Europe's most idyllic places to live in. 'Leroica', a bicycle race is held here  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £129 /night

£900 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Diora C is a characteristic and welcoming apartment that is part of a villa surrounded by vineyards and olive groves. It sleeps four people. From Villa Diora C you will enjoy an enchanting view of the Tuscan hills and of the Chianti valley  …see more

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