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37 Holiday homes in Gaiole in Chianti

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37 Results  |  
23 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

Short stays welcome

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from £114 /night

£795 - £901 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

Apartment | 4 Bedrooms | sleeps 12

Excellent 5/5 

4 Nights min stay

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from £229 /night

£1600 - £2000 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A spacious townhouse complex on two levels well suited to sharing families in easy strolling distance of restaurants, delicatessens, bars etc; large pool, gym, free bicycle hire and plenty of private outdoor space with lovely views offers something for all the family.  …see more

24 Photos

Apartment | 3 Bedrooms | sleeps 8

Excellent 5/5 

4 Nights min stay

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from £172 /night

£1200 - £1500 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A bright roomy south facing 3 bed/2 bath apartment with panaramic views over Gaiole and the hills beyond. Enjoy al fresco dining on the terrace or doze in a wisteria shaded hammock. Relax by the pool, take a cycle ride or just stroll down to the village restuarants. Maggiore is ideally situated to enjoy the areas premier events including Siena Palio and Gaiole Eroica.  …see more

Featured properties

17 Photos

Villa | 6 Bedrooms | sleeps 12

Very Good 4/5 

7 Nights min stay

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from £216 /night

£1512 - £3320 / week

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Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages 5
  • 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 | 1 Bedroom | sleeps 4

Excellent 5/5 

4 Nights min stay

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from £70 /night

£490 - £690 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A spacious 1 bed apartment with garden and bbq terrace, in a picturesque setting, only a short walk to local services. Enjoy free use of cycles & gym or just relax by the pool. Launderette & internet services add home comforts and a glass of wine greets you on arrival. Minore is ideally situated to enjoy the areas premier events including Siena Palio & Gaiole Eroica.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

7 Nights min stay

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from £397 /night

£2776 - £4416 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Private Villa with pool in Gaiole in Chianti in Tuscany sleeping up to 12 people with 5 beds 5 baths in main house and a barn conversion with a separate one bedroomed apartment in the grounds. A great property for large families or groups travelling together.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £80 /night

£560 - £1440 / week

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Late Deal: save up to €400 (approx. £320)

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages 5
  • 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

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £152 /night

£1059 - £1512 / week

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Key info:

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

24 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £60 /night

£416 - £752 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children over
  • 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

20 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

7 Nights min stay

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from £46 /night

£316 - £580 / week

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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 | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £116 /night

£807 - £1109 / week

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Key info:

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

24 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

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from £46 /night

£316 - £580 / week

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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

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from £108 /night

£756 - £1059 / week

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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

9 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £103 /night

£720 - £832 / week

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Key info:

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

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £112 /night

£784 - £904 / week

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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 | 4 Bedrooms | sleeps 7

3 Nights min stay

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from £440 /night

£3080 - £3616 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Gaiole In Chianti with 4 bedrooms sleeps 7  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £341 /night

£2384 - £2800 / week

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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

11 Photos

Farmhouse | 2 Bedrooms | sleeps 7

4 Nights min stay

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from £138 /night

£960 - £1920 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Lecchi with 2 bedrooms sleeps 7  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £152 /night

£1059 - £1512 / week

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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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £103 /night

£720 - £832 / week

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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

22 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £48 /night

£332 - £636 / week

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Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • 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 wine and food in Italy.  …see more

10 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £152 /night

£1059 - £1512 / week

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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

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £162 /night

£1130 - £1612 / week

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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

10 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £112 /night

£784 - £904 / week

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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

8 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

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from £58 /night

£400 - £456 / week

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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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £116 /night

£807 - £1109 / week

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Key info:

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

12 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £123 /night

£861 - £1182 / week

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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

12 Photos

Farmhouse | 3 Bedrooms | sleeps 8

4 Nights min stay

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from £182 /night

£1272 - £2632 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Lecchi with 3 bedrooms sleeps 8  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

Short stays welcome

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from £122 /night

£848 - £2120 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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 £76 /night

£529 - £721 / week

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Key info:

  • Great for children of all ages 5
  • 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

18 Photos

Apartment | 2 Bedrooms | sleeps 2

4 Nights min stay

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from £66 /night

£458 - £560 / week

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Key info:

  • Swimming pool
  • Suitable for children over
  • 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

16 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

Short stays welcome

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from £219 /night

£1527 - £2544 / week

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Key info:

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

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £667 /night

£4664 - £5512 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
VILLA DEL SOLE is a lovely Tuscan villa near the popular towns of Gaiole and Radda in Chianti. This wonderful villa comprises of the main house which is spread over three floors and a separate ground floor villa which is aproximately 50 metres away.  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

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from £66 /night

£459 - £645 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
  • Private garden
This is a quiet and peaceful corner of the property idea for relaxing after sighseeing or for cooling off after the warm Tuscan day. Pool fenced - a 16x6 mtr pool open from mid-May to mid-September (weather permitting)  …see more

13 Photos

Condo | 3 Bedrooms | sleeps 5

2 Nights min stay

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from £43 /night

£297 - £594 / week

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Key info:

  • Great for children of all ages 5
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Nel periodo invernale l'uso del riscaldamento AUTONOMO è a pagamnento euro 4,00 a metro cubo. Tassa di soggiorno dal 6 Aprile al 31 Ottobre da pagare all'arrivo, euro 1,50 a notte per persona per un massimo di sette pernottamenti esclusi i minori fino a 14 anni.  …see more

15 Photos

Villa | 6 Bedrooms | sleeps 14

Short stays welcome

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from £225 /night

£1569 - £2714 / week

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Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Pets welcome
  • Private garden
The "Molino della Carpinese" is located in the municipality of Gaiole in Chianti. The peace and silence characterize the environment that makes it particularly suitable for a relaxing vacation that helps you to forget the stress of those who live in big cities. The Mill of Carpinese is located in the municipality of Gaiole in Chianti, Province of Siena. The peace and  …see more

22 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Min stay varies

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • No pets allowed
  • Private garden
Le Diacce, an enchanting 18th century old farmhouse, belonging to Podere Ciona, 40 hectares of vineyards and woodland, enjoys a unique view on the surrounding hills covered with vineyards, olive groves and woods with Siena in the far distance.  …see more