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66 Holiday homes in Gaiole in Chianti

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66 Results  |  
5 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £49 /night

£342 - £556 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. l  …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

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
  • 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

Featured properties

16 Photos

Farmhouse | 7 Bedrooms | sleeps 13

7 Nights min stay

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from £689 /night

£4823 - £7194 / week

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Key info:

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

15 Photos

Farmhouse | 5 Bedrooms | sleeps 9

7 Nights min stay

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from £492 /night

£3444 - £5057 / week

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Key info:

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

17 Photos

Farmhouse | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £537 /night

£3759 - £6444 / week

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Key info:

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

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

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from £196 /night

£1367 - £1968 / 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

10 Photos

Villa | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £68 /night

£471 - £847 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great 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

2 Nights min stay

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from £49 /night

£342 - £616 / 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

24 Photos

Apartment | 1 Bedroom | sleeps 2

Excellent 5/5 

3 Nights min stay

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from £90 /night

£630 - £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

12 Photos

Townhouse | 1 Bedroom | sleeps 2

1 night min stay

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from £51 /night

£355 - £441 / week

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Key info:

  • Not suitable for children
  • No pets allowed

"Cerbiatto n°5A", 2-room apartment 35 m2 on 2 levels, on the ground floor: living/dining room with satellite-TV. Kitchenette (4 hotplates). On the lower ground floor: 1 double bedroom. Shower/bidet/WC. Small patio. Terrace furniture. Please note: only 1 dog accepted. The showwer  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £191 /night

£1331 - £1664 / 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

20 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4/5 

7 Nights min stay

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from £148 /night

£1033 / 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

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

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from £400 /night

£2799 - £3222 / 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

20 Photos

Villa | 2 Bedrooms | sleeps 4

Very Good 4/5 

7 Nights min stay

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from £72 /night

£500 - £581 / 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 6

3 Nights min stay

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from £81 /night

£565 - £1130 / 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

Castle | 6 Bedrooms | sleeps 14

Short stays welcome

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from £367 /night

£2565 - £3505 / 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

12 Photos

Farmhouse | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £125 /night

£871 - £1139 / week

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Key info:

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

20 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

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from £346 /night

£2420 - £3630 / week

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Key info:

  • Swimming pool
  • Great 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

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

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from £214 /night

£1492 - £1976 / week

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Key info:

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

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £74 /night

£512 - £649 / week

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Key info:

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

8 Photos

Apartment | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £117 /night

£813 - £2069 / 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

9 Photos

B&B | 1 Bedroom | sleeps 2

4 Nights min stay

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from £84 /night

£588 - £1307 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartmentandnbsp;Barnandnbsp;is located in splendid Chianti country side on the ground floor, can comfortably accommodate andnbsp;twoandnbsp;people.andnbsp; There is aandnbsp;double bed roomandnbsp;with open fireplace,andnbsp;small kitchen, bath room with hydro  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £166 /night

£1162 - £1936 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in San Sano with 3 bedrooms sleeps 8  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £348 /night

£2432 - £3648 / week

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Key info:

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

24 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

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from £79 /night

£553 - £1009 / week

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Key info:

  • Nearest beach 107 km
  • Swimming pool
  • Great 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

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £69 /night

£480 - £620 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …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
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Luxury holiday house for 8 persons, with swimming pool , in Chianti  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

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from £91 /night

£633 - £1471 / 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

24 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £209 /night

£1458 - £1611 / 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

24 Photos

Villa | 7 Bedrooms | sleeps 18

5 Nights min stay

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from £185 /night

£1291 - £3500 / 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

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
  • 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

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
  • Great 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 | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £117 /night

£813 - £2069 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole-Apartment Ventoandnbsp;is a andnbsp;threeandnbsp;bedroom rental countryside apartment in the hamlet of Gaiole in theandnbsp;Chianti region of Siena, Tuscany. San Gimignano, a small walled hill town in the province of Siena, is famous for itsandnbsp;medieval  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £77 /night

£539 - £684 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli 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
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 4 persons, with swimming pool , in Siena  …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
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 2 persons, with swimming pool , in Siena  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £345 /night

£2412 - £3468 / 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 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £74 /night

£512 - £649 / week

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Key info:

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

8 Photos

Apartment | 4 Bedrooms | sleeps 6

4 Nights min stay

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from £117 /night

£813 - £2069 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole-Apartment Canopyandnbsp;is a Tuscany rental in the municipality ofandnbsp;Gaiole, Chianti, in Siena, Tuscany. Gaiole in Chianti is a striking little township and rated as one of Europe's most idyllic places to live in. 'Leroica', a bicycle race is held here  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £103 /night

£720 - £879 / week

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Key info:

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

24 Photos

Villa | 2 Bedrooms | sleeps 7

4 Nights min stay

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from £139 /night

£968 - £1476 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

7 Nights min stay

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from £114 /night

£798 - £1709 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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 £184 /night

£1283 - £1920 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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 | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £348 /night

£2432 - £3648 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • 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

21 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 | 4 Bedrooms | sleeps 8

Very Good 4/5 

Short stays welcome

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from £123 /night

£855 - £1197 / 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

13 Photos

Villa | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £77 /night

£533 - £727 / 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

24 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

4 Nights min stay

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from £98 /night

£684 - £761 / 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
L'appartamento " Brunello " è l'ideale per un unico nucleo familiare con bambini Max.6 px. L'Appartamento è composto da tre camere che sono disposte in sequenza e perciò comunicanti e di passo una dopo l'altra. L'appartamento dispone di un bagno con vasca/doccia, lavabo  …see more