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34 Holiday homes in Gaiole in Chianti

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Filters applied: Villa (34)

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34 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

Villa | 2 Bedrooms | sleeps 4

1 night min stay

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from £166 /night

£1162 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
You can upgrade your stay to include 2 Vespa 125cc Scooters for a daily cost of Euro 60 per day per scooter plus IVA tax. Ask when booking about the scooters!  …see more

20 Photos

Villa | 1 Bedroom | sleeps 2

5 Nights min stay

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from £143 /night

£1001 / week

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
You can upgrade your stay to include 2 Vespa 125cc Scooters for a daily cost of Euro 60 per day per scooter plus IVA tax. Ask when booking about the scooters!  …see more

Featured properties

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

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

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

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

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 | 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 | 2 Bedrooms | sleeps 4

Very Good 4/5 

7 Nights min stay

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from £71 /night

£496 - £908 / week

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Key info:

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

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

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

19 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

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from £545 /night

£3809 - £5850 / week

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Key info:

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

20 Photos

Villa | 5 Bedrooms | sleeps 12

2 Nights min stay

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from £569 /night

£3978 - £5511 / week

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Key info:

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

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £207 /night

£1446 - £1903 / 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

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

16 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £684 /night

£4784 - £8416 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
La Maccinaia is a beautiful property located in a very quiet location, in the heart of the Chianti region, between Gaiole and Castelnuovo Berardenga. The main villa dates to the 17th century, and has been immaculately restored by its Belgian owner who combined modern  …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

21 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £275 /night

£1920 - £4500 / 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

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £343 /night

£2400 - £3600 / 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
Villa Eracle is a bright and elegant three-story villa surrounded by vineyards and olive groves. It sleeps eight people. From Villa Eracle you will enjoy a fascinating view of the Chianti hills and of the vineyards  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £343 /night

£2400 - £3600 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Villa Gaiole features all the comforts and a wonderful panoramic Tuscan Villa in Chianti between Siena and Florence, with private pool, air conditioning, total privacy, and a lovely park.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 7

4 Nights min stay

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from £138 /night

£960 - £1464 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
wonderful house, located in Tuscany Italy, has a max. capacity of 7 people. This wonderful house is ideal for families and friends  …see more

24 Photos

Villa | 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
  • Air conditioning
  • No pets allowed
This stunning villa, with 4 bedrooms and 4 bathrooms can accomodate 8 people, so it is ideal for a large group of friends. Located in Tuscany Italy, this villa offers a swimming Pool, air Conditioning, an internet Connection, a pet friendly space .  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 13

3 Nights min stay

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from £960 /night

£6720 - £7840 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This exclusive villa with private swimming pool and tennis court offers luxurious accommodation in Tuscany for 13 people. The apartments and farmhouse can be rented separately or combined with the villa to accommodate up to 35 guests.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £182 /night

£1272 - £1904 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This property in Tuscany Italy is a elegant house that sleeps 8 people, so it is ideal for a large group of friends. The accommodation offers: a swimming Pool .  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £858 /night

£6000 - £7720 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
This exclusive and luxurious villa in Chianti affords 5 bedrooms, dining room, 2 sitting rooms, kitchen, gym, games room and a fabulous infinity swimming pool.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £102 /night

£712 - £816 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This gorgeous house located in Tuscany, Italy, sleeps 8 people and is ideal for large families. The villa features a swimming pool and an Internet connection .  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

Short stays welcome

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from £122 /night

£848 - £2120 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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 £76 /night

£529 - £721 / week

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Key info:

  • Great for children of all ages 5
  • 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 £219 /night

£1527 - £2544 / week

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Key info:

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

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £667 /night

£4664 - £5512 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

11 Photos

Villa | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £303 /night

£2120 - £2205 / week

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Key info:

  • Suitable for children over
  • 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

15 Photos

Villa | 6 Bedrooms | sleeps 12

1 night min stay

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from £182 /night

£1272 - £1951 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Tranquilla Confortevole Cibo Cucina Salumi Vino Olio Piscina Palestra Panorama Chianti Castello  …see more

15 Photos

Villa | 6 Bedrooms | sleeps 14

Short stays welcome

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from £225 /night

£1569 - £2714 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
  • Private garden
The "Molino della Carpinese" is located in the municipality of Gaiole in Chianti. The peace and silence characterize the environment that makes it particularly suitable for a relaxing vacation that helps you to forget the stress of those who live in big cities. The Mill of Carpinese is located in the municipality of Gaiole in Chianti, Province of Siena. The peace and  …see more