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94 Holiday homes in Gaiole in Chianti

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94 Results  |  
18 Photos

Villa | 4 Bedrooms | sleeps 8

Short stays welcome

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from £122 /night

£848 - £2120 / week

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Key info:

  • Swimming pool
  • Suitable for children over
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Tuscany. Heart of Chiant.iExclusive use of private swimming pool. The Villa accommodates up to 8/9 people. Beautiful views of the country side. Only a few other farmhouses are visible in the distance. Outdoor dining area. Fontecaresino, located in the hills of Chianti, in the heart of Tuscany. Breathtaking views.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £38 /night

£265 - £658 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

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
  • Great for children of all ages 5
  • 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

Featured properties

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
  • Great for children of all ages 5
  • 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

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £216 /night

£1512 - £3320 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages 5
  • 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 | 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
  • Great for children of all ages 5
  • 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

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £194 /night

£1356 - £3004 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

House | 1 Bedroom | sleeps 3

2 Nights min stay

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from £49 /night

£340 - £679 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to enjoy the calm, the beauty and all the pleasures our region has to offer. Our apartments have been renovated with respect for tradition.  …see more

10 Photos

Villa | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £67 /night

£467 - £933 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

Apartment | 1 Bedroom | sleeps 2

Excellent 5/5 

3 Nights min stay

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from £70 /night

£490 - £770 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Ideal for couples seeking relaxation "Home from Home". Everything you need in walking distance to the village, private garden with views over the village, covered decking & pergola perfect for "al fresco" dining, patio heater, BBQ, sun loungers. Read our Guest Reviews There are five restaurants within walking distance and numerous more a short drive away. FREE WI-FI  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4/5 

7 Nights min stay

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from £147 /night

£1024 - £1712 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Vignale is a small hamlet that has a total of 6 private homes. It is located on top of a Chianti hill that gives it the luxury of a stunning view all around. Within a short drive there are three of the five famous Chianti towns.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

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from £397 /night

£2776 - £4416 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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 | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £189 /night

£1320 - £2200 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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 | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £80 /night

£560 - £1440 / week

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Late Deal: save up to €400 (approx. £320)

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

Castle | 6 Bedrooms | sleeps 14

Short stays welcome

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from £364 /night

£2544 - £3562 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

12 Photos

Farmhouse | 4 Bedrooms | sleeps 7

2 Nights min stay

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from £223 /night

£1560 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 4 bedrooms sleeps 7  …see more

8 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £108 /night

£756 - £924 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £212 /night

£1480 - £1960 / week

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Key info:

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

10 Photos

B&B | 1 Bedroom | sleeps 4

1 night min stay

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from £102 /night

£712 - £904 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £111 /night

£773 - £872 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 2 bedrooms sleeps 4  …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 5
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Luxury holiday house for 8 persons, with swimming pool , in Chianti  …see more

10 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

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from £75 /night

£524 - £616 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 7

4 Nights min stay

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from £138 /night

£960 - £1920 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Lecchi with 2 bedrooms sleeps 7  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £341 /night

£2384 - £2800 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 6

2 Nights min stay

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from £206 /night

£1440 - £1680 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 4 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £155 /night

£1080 - £1280 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £74 /night

£516 - £615 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

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from £84 /night

£583 - £1296 / 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

12 Photos

Farmhouse | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £134 /night

£936 - £1130 / week

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Key info:

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

10 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £112 /night

£784 - £904 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £141 /night

£986 - £1176 / 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 Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

20 Photos

House | 4 Bedrooms | sleeps 7

1 night min stay

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from £426 /night

£2980 - £3500 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £79 /night

£550 - £644 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £152 /night

£1059 - £1512 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £120 /night

£840 - £1008 / 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 Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 5

2 Nights min stay

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from £206 /night

£1440 - £1680 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 5  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

7 Nights min stay

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from £46 /night

£316 - £580 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
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

16 Photos

House | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £488 /night

£3416 - £5016 / week

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Key info:

  • Great for children of all ages 5
  • 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

20 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

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from £79 /night

£548 - £1248 / week

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Key info:

  • Nearest beach 107 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £345 /night

£2412 - £3619 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 4 bedrooms sleeps 8  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

5 Nights min stay

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from £183 /night

£1280 - £4592 / 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

10 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

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from £82 /night

£572 - £712 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …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 5
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 4 persons, with swimming pool , in Siena  …see more

16 Photos

House | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £591 /night

£4136 - £6080 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

9 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £120 /night

£840 - £1008 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £116 /night

£807 - £1109 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

10 Photos

B&B | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £102 /night

£712 - £904 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 4  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £141 /night

£986 - £1176 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

10 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £82 /night

£572 - £712 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Bed & Breakfast 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 £79 /night

£550 - £644 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more