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37 Holiday homes in Gaiole in Chianti

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37 Results  |  
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 | 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

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

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £194 /night

£1356 - £2252 / 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

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

20 Photos

Villa | 2 Bedrooms | sleeps 4

Very Good 4/5 

7 Nights min stay

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from £71 /night

£496 - £668 / 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 | 6 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

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from £397 /night

£2776 - £3616 / 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 8

Very Good 4/5 

7 Nights min stay

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from £147 /night

£1024 - £1148 / 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

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

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

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

12 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £138 /night

£960 - £1280 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
  • Private garden
Apartment / Condo in Lecchi with 3 bedrooms sleeps 6  …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

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

12 Photos

Farmhouse | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £182 /night

£1272 - £2632 / 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 3 bedrooms sleeps 8  …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

24 Photos

Villa | 7 Bedrooms | sleeps 18

5 Nights min stay

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from £183 /night

£1280 - £3472 / 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

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

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

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 | 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

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £102 /night

£712 - £1696 / 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

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 | 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

21 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £78 /night

£540 - £796 / week

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Key info:

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

13 Photos

Guest house | 5 Bedrooms | sleeps 12

1 night min stay

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from £124 /night

£868 - £1198 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Our Gaiole in Chianti, Tuscany vacation rental Guest House is the perfect place for a family vacation, or just a getaway with friends  …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

21 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £66 /night

£459 - £484 / week

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Key info:

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

15 Photos

Villa | 6 Bedrooms | sleeps 12

1 night min stay

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from £182 /night

£1272 - £1612 / 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

12 Photos

House | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £73 /night

£509 - £721 / week

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Key info:

  • Not suitable for children
  • Car essential
  • Some pets are welcome - please contact the owner
Casa colonica chiantigiana di grande charme, comoda e arredata con gusto e attenzione al dettaglio.  …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

8 Photos

House | 2 Bedrooms | sleeps 4

Min stay varies

Add to shortlist

Key info:

  • Great for children of all ages 5
  • No pets allowed
Siamo nel cuore del paese. Due passi per raggiunbere l'edicola, il tabaccaio, il market, la farmacia etc.  …see more

16 Photos

Farmhouse | 6 Bedrooms | sleeps 11

Min stay varies

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from £555 /night

£3880 - £5824 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
  • Private garden
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

15 Photos

Farmhouse | 5 Bedrooms | sleeps 9

Min stay varies

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from £455 /night

£3184 - £4784 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

17 Photos

Farmhouse | 7 Bedrooms | sleeps 18

Min stay varies

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from £695 /night

£4864 - £8416 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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 | 7 Bedrooms | sleeps 13

Min stay varies

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from £647 /night

£4528 - £6880 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

22 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Min stay varies

Add to shortlist

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • 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