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56 Holiday homes in Gaiole in Chianti

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56 Results  |  
17 Photos

Farmhouse | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £537 /night

£3759 - £6444 / 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

16 Photos

Farmhouse | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £596 /night

£4170 - £6130 / 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

16 Photos

Farmhouse | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £689 /night

£4823 - £7194 / 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

Featured properties

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £196 /night

£1367 - £1968 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This comfortably furnished country style Tuscan villa sleeps up to ten persons. Set amongst a mature well tended garden with its own private swimming pool. The property is in a great location only five minutes away from Gaiole.  …see more

10 Photos

Villa | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £68 /night

£471 - £847 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
The Chianti As You Always Dreamed It. A charming Medieval borgo in the heart of Chianti Classico, 15 km far from Siena. Relax and discovery hour incredible landes. The charme of an ancient Medieval borgo in the heart of Chianti Classico  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

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from £400 /night

£2799 - £3222 / 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

20 Photos

Villa | 2 Bedrooms | sleeps 4

Very Good 4/5 

7 Nights min stay

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from £72 /night

£500 - £581 / 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

Castle | 6 Bedrooms | sleeps 14

Short stays welcome

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from £367 /night

£2565 - £3505 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Castle, tuscany, italy, swimmingpool, bed and breakfast, gaiole in chianti, events, wedding, private castle, private villa, Yoga, wine  …see more

16 Photos

House | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £492 /night

£3444 - £3565 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Il Colombaio is a peaceful oasis in the heart of Chianti Classico, with expansive views on rolling hills and rows of vineyards. The location, near the village of Gaiole in Chianti, is perfect for visiting the several hilltop villages such as Radda, Castellina and Greve  …see more

9 Photos

B&B | 1 Bedroom | sleeps 2

4 Nights min stay

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from £84 /night

£588 - £1307 / 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

12 Photos

Farmhouse | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £125 /night

£871 - £1139 / 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

16 Photos

House | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £689 /night

£4823 - £5073 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Il Colombaio is a peaceful oasis in the heart of Chianti Classico, with expansive views on rolling hills and rows of vineyards. The location, near the village of Gaiole in Chianti, is perfect for visiting the several hilltop villages such as Radda, Castellina and Greve,  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £166 /night

£1162 - £1936 / 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

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £77 /night

£539 - £684 / 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

Villa | 7 Bedrooms | sleeps 18

5 Nights min stay

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from £185 /night

£1291 - £3500 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Villa Il Giglio is a charming private villa located in the Chianti Senese area surrounded by a spacious 6000 sq mt parkland which is completely fenced in though giving access through an electronic gate. The villa has a lovely swimming pool ( 6 x 12 mts) with a  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £344 /night

£2404 - £2952 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
This particular and fascinating farmhouse is located in the heart of Chianti, a region renowned worldwide for its wine production. The property has a great and particular charm and although maintaining the rural character of the structure and the classic style typical  …see more

10 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £153 /night

£1067 - £1525 / 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

19 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £118 /night

£826 - £930 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 4 persons, with swimming pool , in Siena  …see more

8 Photos

B&B | 2 Bedrooms | sleeps 2

4 Nights min stay

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from £84 /night

£588 - £1307 / 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

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £109 /night

£763 - £1067 / 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

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £74 /night

£512 - £649 / 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

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £91 /night

£633 - £1471 / 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

21 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £277 /night

£1936 - £4537 / 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £371 /night

£2596 - £3894 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Luxury holiday house for 8 persons, with swimming pool , in Chianti  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £153 /night

£1067 - £1525 / 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

8 Photos

Apartment | 4 Bedrooms | sleeps 6

4 Nights min stay

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from £117 /night

£813 - £2069 / 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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £103 /night

£720 - £879 / 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

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £135 /night

£945 - £2291 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
This beautiful, detached farmhouse has been carefully restored by the architect owner to the highest standards. He has maintained the original structure, while adding modern design ideas.  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

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from £84 /night

£588 - £1307 / 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

8 Photos

Apartment | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £117 /night

£813 - £2069 / 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

16 Photos

Apartment | 1 Bedroom | sleeps 2

7 Nights min stay

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from £85 /night

£591 - £689 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 2 persons, with swimming pool , in Siena  …see more

12 Photos

Apartment | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £117 /night

£813 - £2069 / 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

16 Photos

House | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £596 /night

£4170 - £4275 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Il Colombaio is a peaceful oasis in the heart of Chianti Classico, with expansive views on rolling hills and rows of vineyards. The location, near the village of Gaiole in Chianti, is perfect for visiting the several hilltop villages such as Radda, Castellina and Greve  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £74 /night

£512 - £649 / 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

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £69 /night

£480 - £620 / 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

12 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £91 /night

£633 - £1471 / 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

20 Photos

Apartment | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £143 /night

£998 - £1205 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 5 persons, with swimming pool , in Siena  …see more

16 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £162 /night

£1130 - £1612 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Apartment for 6 persons, with swimming pool , in Chianti  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £214 /night

£1492 - £1976 / 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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £117 /night

£813 - £1118 / 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

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £209 /night

£1458 - £1611 / 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

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £348 /night

£2432 - £3648 / 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

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £153 /night

£1067 - £1525 / 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

17 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

Short stays welcome

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from £123 /night

£855 - £1197 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, and 55 km from Florence. EXCLUSIVE USE of the Swimming Pool! The swimming pool is available from April 1 to October 15, it may varies depending on weather conditions.  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £77 /night

£533 - £727 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Fontecaresino 2 when rented without Fontecaresino 1 does not have access to the swimming pool.  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

Short stays welcome

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from £220 /night

£1539 - £1881 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
2 Villas in the heart of Chianti with the exclusive use of a swimming pool! Beautiful, isolated property with breathtaking views of the hills of Tuscany. The villas are located close by to Gaiole in Chianti and all the cultural and artistic activities of the region.  …see more

8 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £68 /night

£471 - £599 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
Un posto accogliente e familiare, ideale per chi vuole scoprire la terra del buon vino tra famosi vigneti e affascinanti castelliSiamo nel cuore del paese. Due passi per raggiunbere l'edicola, il tabaccaio, il market, la farmacia etc. La biancheria da letto, bagno e cucina è inclusa nel prezzo. Extra: garage e fornitura legna camino.  …see more

41 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £672 /night

£4702 - £5557 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
VILLA DEL SOLE is a lovely Tuscan villa near the popular towns of Gaiole and Radda in Chianti. This wonderful villa comprises of the main house which is spread over three floors and a separate ground floor villa which is aproximately 50 metres away.  …see more

19 Photos

Villa | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £147 /night

£1026 / week

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Key info:

  • Suitable for children over
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Experience Tuscany cooking class, Italian dining and Tuscany tours to Siena, Cortona, San Giminiano and the wine regions of Montalcino and Montepulciano, Pienza, Volterra. Villa Oliviera is a really ' A Taste of Tuscany ' in an authentic, unique, Tuscany Villa Breakfast with home made specialities is served in a charming patio in the stunning Chianti wines view.  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £67 /night

£463 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This is a quiet and peaceful corner of the property idea for relaxing after sighseeing or for cooling off after the warm Tuscan day. Pool fenced - a 16x6 mtr pool open from mid-May to mid-September (weather permitting)  …see more