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Country estate for 15 people in a beautiful location in the Val d’Orcia.
1/4Between cypresses and cycadsTuscany | Whether a restored farm house or agriturismo – during a country vacation in Tuscany you can experience the nature and regional cuisine.
Per week from USD 394
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Holiday home for max. 6 persons on Sicily
2/4Holiday with your own poolItaly | Give your Italian holiday the perfect touch in a holiday home with its own pool: Splash about with the whole family in the water or let yourself completely relax.
Per week from USD 537
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Studio for max. 4 persons on the Italian Adriatic Coast
3/4Fun for the entire familyItalian Adriatic | A vacation in a holiday park is particularly ideal for families. As parents you can lean back and relax whilst your kids are taken care of your hands and are fully entertained.
Per week from USD 441
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4/4Vacation with your dogItaly | With these holiday houses it is explicitely allowed to bring pets so that your faithful four legged friend can also enjoy a relaxing and eventful holiday.
Per week from USD 460
show 11,863 offers
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Tuscany | Vacation on a country estate
491 offers -
Italy | Holiday with your own pool
4,756 offers -
Italian Adriatic | Vacation in a holiday park
307 offers -
Italy | Vacation with your dog
11,863 offers
Peaceful holiday home vacation in gorgeous Chianti
No holiday home ever totally feels like home, but you may have a hard time going home after getting a taste of Chianti. It's world-famous for its red wine, but it's the rolling landscapes, quaint villages and rich culture that truly set this area of central Italy apart. Whether you want to throw yourself into non-stop wine tours, explore some stunning countryside, hike mountains, or simply blob out with a book, a holiday apartment in Chianti will not disappoint.
You're on holiday - lap it up!
It is no secret that Chianti is home to some of Tuscany's most famous and impressive wineries, and there are too many fabulous vineyards to visit in one lifetime, let alone one holiday home getaway. However, a good way to start is placing yourself in a holiday apartment in the picturesque towns of Greve or Gaiole where you can get a little slice of local Italian life while also being surrounded by stunning landscapes and almost embarrassingly consistently good weather (hence the quality of the wine). Better yet, these two spots are great gateways to many vineyards offering tastings, tours or simply a good family meal very close to your accommodation.
Holiday homes suiting culture vultures and active holiday-makers alike
Few places manage to do both well, but Chianti really does offer something for everyone. Tuscany's good weather (though never insufferably hot) and sparsely populated, lush countryside offer many opportunities for hiking, cycling or swimming, no matter how young or old you are (or feel). With such stunning natural landscapes at hand, it may feel strange that just a short trip from your Chianti holiday home are the world-class cultural gems of Siena - especially its iconic cathedral and main square - and Florence, whose historical and artistic wealth is matched by very few cities. But that's exactly the case when you rent a holiday home or flat for you, your loved ones or a group of friends in Chianti.
Neighbouring holiday regions Chianti
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San Casciano in Val di Pesa, Chianti
Holiday apartment for max. 4 persons
Property no. 1025954
+ 5 morefrom USD 2,344for 1 weekApprox. 40 m², 1 bedroom, 1 bathroom, pets not allowed, satellite TV, Wifi, dishwasher, non-smoking property, sandy beach approx. 110 km, farm holidays, sea/lake view, communal swimming pool, Country estate, Wine-growing estate -
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Ambra, Chianti
Holiday home for max. 4 persons
Property no. 3501442
+ 3 morefrom USD 901for 1 weekApprox. 55 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property, sandy beach approx. mThere are 3 further property types with 3 accommodations for this complex- from USD 860/week Holiday home for max. 4 persons, approx. 55 m², property no. 3501446 Preview
- from USD 860/week Holiday home for max. 4 persons, approx. 60 m², property no. 3501449 Preview
- from USD 1,069/week Holiday home for max. 6 persons, approx. 85 m², property no. 3501456 Preview
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Castellina in Chianti, Chianti
Holiday apartment for max. 4 persons
Property no. 264413
+ 2 moreApprox. 85 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, farm holidaysThere are 2 further property types with 2 accommodations for this complex- Rental price on request Holiday home for max. 4 persons, approx. 90 m², property no. 261343 Preview
- Rental price on request Holiday home for max. 4 persons, approx. 90 m², property no. 261344 Preview
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San Donato in Poggio, Chianti
Holiday apartment for max. 4 persons
Property no. 3501725
+ 4 morefrom USD 1,053for 1 weekApprox. 90 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property, sandy beach approx. m, farm holidaysThere are 4 further property types with 4 accommodations for this complex- from USD 611/week Holiday apartment for max. 2 persons, approx. 50 m², property no. 3501712 Preview
- from USD 878/week Holiday apartment for max. 4 persons, approx. 70 m², property no. 3501715 Preview
- from USD 1,053/week Holiday apartment for max. 4 persons, approx. 80 m², property no. 3501720 Preview
- from USD 1,053/week Holiday apartment for max. 4 persons, approx. 62 m², property no. 3501727 Preview
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Lilliano, Chianti
Holiday home for max. 7 persons
Property no. 124161
from USD 2,075for 1 weekApprox. 150 m², 4 bedrooms, 3 bathrooms, pets are allowed (max. 2) (from 01/01/2025), satellite TV (from 01/01/2025), Wifi (from 01/01/2025), washing machine (from 01/01/2025), dishwasher (from 01/01/2025), non-smoking property (from 01/01/2025), private pool (from 01/01/2025)
