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90 Holiday homes in Gaiole in Chianti

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90 Results  |  
24 Photos

Apartment | 1 Bedroom | sleeps 2

Excellent 5/5 

3 Nights min stay

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from £70 /night

£490 - £690 / week

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Late Deal: save up to £74

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

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £38 /night

£265 - £742 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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
  • Suitable 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

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
  • Suitable 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

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
  • Suitable 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

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £224 /night

£1562 - £3430 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • 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

15 Photos

Farmhouse | 5 Bedrooms | sleeps 9

Min stay varies

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from £470 /night

£3290 - £4943 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 £718 /night

£5025 - £8695 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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 £669 /night

£4678 - £7108 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

16 Photos

Farmhouse | 6 Bedrooms | sleeps 11

Min stay varies

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from £573 /night

£4009 - £6017 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

Short stays welcome

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from £80 /night

£557 - £901 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable 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

13 Photos

B&B | 1 Bedroom | sleeps 2

Min stay varies

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from £76 /night

£526 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Borgo in genuine Chianti town. Scenery perfect for hiking and biking. Proximity to Siena and Florence alongside other cultural and historical Chianti villages. Excellent local dining and wine tasting. Property provides easy access to spacious terrace and pool area.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £83 /night

£579 - £1488 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable 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

13 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £49 /night

£341 - £865 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'La Colomba n°4', 3-room apartment 75 m2 on 2 levels, on the ground floor: living room with 1 double sofa bed (160 cm), satellite-TV. Kitchenette (4 hotplates). Shower/WC. Upper floor: 1 double bedroom. 1 room with 2 beds. Shower/bidet/WC. Small patio. Terrace  …see more

7 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £34 /night

£235 - £502 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'Prugnolino n°7', 1-room apartment 25 m2, on the ground floor: 1 double bedroom with satellite-TV. Kitchen (2 hotplates) with dining table. Shower/WC. Maximum 1 pet/ dog allowed. Private outdoor area, 6 m2, furnished with 2 loungers and sunbed. Farm hou  …see more

6 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £40 /night

£279 - £570 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'Trebbiano n°5', 2-room apartment 40 m2, on the lower ground floor: living/dining room with satellite-TV. 1 double bedroom with 1 bed and 1 double bed. Kitchenette. Shower/WC. Maximum 1 pet/ dog allowed. Farm house Ensoli, approx 1600, has been recently  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £50 /night

£346 - £831 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'La Farfalla n°5', 3-room apartment 75 m2 on 2 levels, on the ground floor: living/dining room with 1 double sofa bed (160 cm), satellite-TV. Kitchenette (4 hotplates). Sep. WC. Upper floor: 1 double bedroom. 1 room with 2 beds. Shower/bidet/WC. Small patio. T  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £47 /night

£329 - £659 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'Il Pettirosso n°7', 2-room apartment 55 m2 on 2 levels, on the ground floor: kitchen (4 hotplates) with dining table and satellite-TV. Upper floor: 1 double bedroom. 1 room with 2 beds. Shower/bidet/WC. Small patio. Terrace furniture. Maximum 1 pet/ dog allow  …see more

13 Photos

Apartment | 7 Bedrooms | sleeps 16

3 Nights min stay

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from £123 /night

£859 - £1758 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'Il Gufo n°1', 9-room apartment 180 m2 on 2 levels on 1st floor: living/dining room with open fireplace. Small living room with 1 double sofa bed (160 cm), satellite-TV. 1 double bedroom. Kitchenette (4 hotplates, dishwasher, micro wave). Shower/WC. Upper floo  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £76 /night

£530 - £558 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'Casa Selvolini', 4-room apartment 80 m2 on 1st floor, comfortable furnishings: open living/dining room with open fireplace, digital TV and air-conditioning. Exit to the terrace. 1 double bedroom. 1 room with 2 beds. Small lounge. Kitchenette (4 hotplates, ove  …see more

9 Photos

Apartment | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £62 /night

£430 - £1022 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'San Giovese n°4', 4-room apartment 105 m2, on the upper ground floor: living room with satellite-TV. 1 room with 1 bed and 1 double bed. 1 double bedroom. 1 room with 1 bed. Kitchen (4 hotplates, dishwasher) with open fireplace and dining table. Shower/WC, sh  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £50 /night

£346 - £731 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'Coccinella n°6', 3-room apartment 50 m2, on the upper ground floor: living/dining room with 1 double sofa bed (160 cm), satellite-TV. 1 double bedroom. 1 room with 2 beds. Kitchenette (4 hotplates). Shower/bidet/WC. Small patio. Terrace furniture. Maximum 1 p  …see more

6 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

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from £49 /night

£341 - £670 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'Malvasia n°6', 3-room apartment 60 m2, on the lower ground floor: living/dining room with 1 double sofa bed and satellite-TV. 1 double bedroom. 1 room with 1 x 2 bunk beds. Kitchenette. Shower/bidet/WC. Maximum 1 pet/ dog allowed. Farm house Ensoli, ap  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £42 /night

£290 - £614 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
'Pulcino n°3', 2-room apartment 32 m2, on the ground floor: living/dining room with 1 double sofa bed (160 cm), satellite-TV. 1 small double bedroom. Kitchenette. Shower/WC. Small patio. Maximum 1 pet/ dog allowed. Località la Massa 15 km from Gaiole in  …see more

22 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Min stay varies

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable 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

9 Photos

Apartment | 3 Bedrooms | sleeps 8

1 night min stay

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from £57 /night

£399 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
Just a few minutes far from the small village of Montegrossi where you are staying in our home holiday, you can discover the architectural, natural and gourmet marvels of Classic Chianti, Florentine Chianti and Sienese Chianti…  …see more

24 Photos

Castle | 6 Bedrooms | sleeps 14

Min stay varies

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from £94 /night

£658 - £3592 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Castle, tuscany, italy, swimmingpool, bed and breakfast, gaiole in chianti, events, wedding, private castle, private villa, Yoga, wine  …see more

10 Photos

Villa | 2 Bedrooms | sleeps 5

Min stay varies

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from £69 /night

£482 - £964 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable 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

House | 1 Bedroom | sleeps 3

Min stay varies

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from £51 /night

£351 - £701 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable 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

24 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £62 /night

£430 - £777 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • May take pets – please enquire
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

11 Photos

Villa | 6 Bedrooms | sleeps 14

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Splendid Tuscan Castle which dates back to the year 1000, perched on the edge of a tiny hamlet, immersed in one of the most beautiful scenic havens in the Chianti region and surrounded by breathtaking panorama of the soft rolling vineyards.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

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from £81 /night

£567 - £1290 / week

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Key info:

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

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £142 /night

£992 - £2404 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • May take pets – please enquire
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

16 Photos

House | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £707 /night

£4943 - £7372 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

7 Nights min stay

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from £47 /night

£327 - £600 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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

12 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £93 /night

£648 - £1507 / 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

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

16 Photos

House | 5 Bedrooms | sleeps 12

7 Nights min stay

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from £551 /night

£3852 - £6604 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

8 Photos

B&B | 2 Bedrooms | sleeps 2

3 Nights min stay

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from £86 /night

£602 - £1339 / 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

20 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £355 /night

£2480 - £3720 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

16 Photos

House | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £505 /night

£3529 - £5182 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • 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

8 Photos

Apartment | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £120 /night

£834 - £2120 / 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

House | 6 Bedrooms | sleeps 11

7 Nights min stay

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from £611 /night

£4273 - £6281 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

21 Photos

Villa | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £284 /night

£1984 - £4649 / 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

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
  • Suitable for children of all ages
  • Car not necessary
  • 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

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £352 /night

£2463 - £3967 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • 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

20 Photos

House | 4 Bedrooms | sleeps 7

1 night min stay

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from £550 /night

£3850 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Diora A is a splendid sixteenth-century two-story apartment that is part of a villa situated in the heart of the Tuscan countryside. It sleeps seven people. From Villa Diora A you will enjoy an enchanting view of the Chianti hills and of the vineyards  …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
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 5 persons, with swimming pool , in Siena  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £86 /night

£602 - £1339 / 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

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