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29 Holiday homes in Gaiole in Chianti

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29 Results  |  
16 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

Short stays welcome

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from £208 /night

£1452 - £1654 / 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

13 Photos

Villa | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £93 /night

£646 - £686 / 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

23 Photos

Apartment | 2 Bedrooms | sleeps 6

Very Good 4.5/5 

Min stay varies

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from £75 /night

£525 - £850 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Apartment with spectacular views in the heart of the Chianti Region in Tuscany. A €150 deposit for air con payable on arrival usage will be calculated and refund given.€1.50 p/n local tax  …see more

Featured properties

24 Photos

Castle | 6 Bedrooms | sleeps 14

Short stays welcome

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from £346 /night

£2420 - £3307 / 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

18 Photos

Villa | 4 Bedrooms | sleeps 8

Short stays welcome

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from £93 /night

£646 - £1855 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • 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

21 Photos

Villa | 2 Bedrooms | sleeps 4

1 night min stay

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from £158 /night

£1105 / 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

24 Photos

House | 1 Bedroom | sleeps 3

2 Nights min stay

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from £47 /night

£323 - £581 / week

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Key info:

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

20 Photos

House | 3 Bedrooms | sleeps 5

4 Nights min stay

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from £83 /night

£581 - £722 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • Some pets are welcome - please contact the owner
maison toscane, appartement, piscine, chianti, gaiole in chianti, Sienne, visites de producters de vin, dégustations de vin, outlet shopping, siteseeing, marcher, villes d'art, repos, grand panorama, avec restaurant et bar, familiaire,chiens bien venus. Distances airport 60km gare 16km emplettes 10 km hopital 16 km  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 14

Short stays welcome

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from £214 /night

£1492 - £2581 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

24 Photos

Farmhouse | 6 Bedrooms | sleeps 12

2 Nights min stay

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from £329 /night

£2300 / 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
Podere Scopeto, a former hill farm on sunset-facing slopes of the Chianti in the heart of the wine-region. Main House sleeps 10 and separately available self-contained studio for 2 in its own 30 acres of woodland. 15m saltwater pool on terraces with spectacular views.  …see more

41 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £634 /night

£4436 - £5242 / 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

20 Photos

Villa | 1 Bedroom | sleeps 2

5 Nights min stay

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from £136 /night

£952 / 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

18 Photos

Apartment | 2 Bedrooms | sleeps 2

4 Nights min stay

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from £57 /night

£396 - £533 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • Pets welcome
Siena (Km30), Monteriggioni, Colle Val d'Elsa, Firenze (Km60), San Gimigniano, Volterra, Arezzo to reache into an hour APT. 1) 4 LOCATAIRES APT. 7) 2 " APT.8) 6 " APT.4) 8 " APT.5) 6 "  …see more

15 Photos

Villa | 6 Bedrooms | sleeps 12

1 night min stay

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from £173 /night

£1210 / week

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Key info:

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

21 Photos

Villa | 2 Bedrooms | sleeps 4

Very Good 4/5 

7 Nights min stay

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from £72 /night

£500 - £916 / 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

Villa | 3 Bedrooms | sleeps 8

Very Good 4/5 

7 Nights min stay

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from £148 /night

£1033 - £1726 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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 | 2 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £69 /night

£480 - £803 / 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

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £218 /night

£1525 - £3347 / 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 | 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 £191 /night

£1331 - £2218 / 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 | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £196 /night

£1367 - £3029 / 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

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 | 6 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

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from £346 /night

£2416 - £4452 / 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

22 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £70 /night

£490 - £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

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

24 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £81 /night

£565 - £968 / 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

24 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £60 /night

£416 - £755 / 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

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

17 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

Short stays welcome

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from £93 /night

£646 - £1855 / 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

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