List your home
Apply filters
£ to

143 Holiday homes in Gaiole in Chianti

Reset search

Show results on map

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
Rome
2,539 properties
Florence
977 properties
Trapani
511 properties
Venice, Veneto
492 properties
Amalfi Coast
465 properties
Lucca
427 properties
Cortona
419 properties
Palermo
418 properties
Sorrento, Campania
355 properties
Cefalu
310 properties
San Gimignano
298 properties
Taormina
270 properties
Greve in Chianti
269 properties
Alghero
259 properties
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
143 Results  |  
12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £79 /night

£550 - £644 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

10 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £75 /night

£524 - £616 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £118 /night

£826 - £930 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 4 persons, with swimming pool , in Siena  …see more

Featured properties

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £137 /night

£954 - £2312 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £155 /night

£1080 - £1280 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

21 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £275 /night

£1920 - £4500 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Enrichettaandnbsp;is located in a charming medieval hamlet set in one of the most idyllic Tuscan scenery, surrounded by gently rolling, green hills and vineyards. The villa in authentic Chianti style is linear, luminous, almost a sculpture built onandnbsp;three  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £569 /night

£3978 - £5511 / week

View

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

10 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £82 /night

£572 - £712 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £123 /night

£861 - £1182 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Chianti  …see more

16 Photos

House | 5 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £488 /night

£3416 - £5016 / week

View

Key info:

  • Great for children of all ages 5
  • 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

24 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £46 /night

£316 - £580 / week

View

Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages 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

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £108 /night

£756 - £1059 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £342 /night

£2392 - £3440 / week

View

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

8 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £58 /night

£400 - £456 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

16 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £162 /night

£1130 - £1612 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Apartment for 6 persons, with swimming pool , in Chianti  …see more

9 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £103 /night

£720 - £832 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £152 /night

£1059 - £1512 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

16 Photos

House | 7 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £684 /night

£4784 - £7136 / week

View

Key info:

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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £103 /night

£720 - £832 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £111 /night

£773 - £872 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 2 bedrooms sleeps 4  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £143 /night

£998 - £1205 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Apartment for 5 persons, with swimming pool , in Siena  …see more

10 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £82 /night

£572 - £712 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Bed & Breakfast in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

10 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £112 /night

£784 - £904 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £112 /night

£784 - £904 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

9 Photos

B&B | 1 Bedroom | sleeps 2

4 Nights min stay

Add to shortlist

from £84 /night

£583 - £1296 / week

View

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

19 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £545 /night

£3809 - £5850 / week

View

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

8 Photos

B&B | 2 Bedrooms | sleeps 2

4 Nights min stay

Add to shortlist

from £84 /night

£583 - £1296 / week

View

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

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £83 /night

£579 - £679 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £141 /night

£986 - £1176 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £116 /night

£807 - £1109 / week

View

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 Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

16 Photos

House | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £533 /night

£3728 - £6392 / week

View

Key info:

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

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £141 /night

£986 - £1176 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £46 /night

£316 - £580 / week

View

Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • 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

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £120 /night

£840 - £1008 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 3

2 Nights min stay

Add to shortlist

from £132 /night

£920 - £1080 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 3  …see more

8 Photos

Apartment | 4 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £116 /night

£807 - £2052 / week

View

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

Add to shortlist

from £116 /night

£807 - £1109 / week

View

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 Gaiole In Chianti with 2 bedrooms sleeps 4  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

5 Nights min stay

Add to shortlist

from £183 /night

£1280 - £4592 / week

View

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

Apartment | 3 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £116 /night

£807 - £2052 / week

View

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

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £120 /night

£840 - £1008 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £79 /night

£548 - £1248 / week

View

Key info:

  • Nearest beach 107 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Located within walking distance of the village of Gaiole in Chianti, the villa offers the perfect setting to explore the Chianti Classico region, enjoy the breathtaking views of the vineyards and olive groves, and experience the charming Tuscan lifestyle. Beautiful villa located within walking distance of the village of Gaiole in Chianti, near Siena, Tuscany  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £90 /night

£628 - £1459 / week

View

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

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £141 /night

£986 - £1176 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Villa / Farmhouse / Home in Gaiole In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 8

4 Nights min stay

Add to shortlist

from £182 /night

£1272 - £2632 / week

View

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

16 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £684 /night

£4784 - £8416 / week

View

Key info:

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

12 Photos

Farmhouse | 4 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £206 /night

£1440 - £1680 / week

View

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

3 Nights min stay

Add to shortlist

from £858 /night

£6000 - £7720 / week

View

Key info:

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

24 Photos

Villa | 2 Bedrooms | sleeps 7

4 Nights min stay

Add to shortlist

from £1 /night

£1 - £1920 / week

View

Key info:

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

24 Photos

Villa | 3 Bedrooms | sleeps 8

4 Nights min stay

Add to shortlist

from £182 /night

£1272 - £1904 / week

View

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 | 7 Bedrooms | sleeps 13

3 Nights min stay

Add to shortlist

from £960 /night

£6720 - £7840 / week

View

Key info:

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