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Holiday houses in Chianti & holiday apartments in Chianti

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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.


  • Montevarchi, Chianti

    Holiday home for max. 5 persons

    Property no. 124100
    from USD 1,394
    for 1 week
    Approx. 80 m², 2 bedrooms, 2 bathrooms, pets not allowed, satellite TV, Wifi, washing machine, dishwasher, non-smoking property, sauna,
    4.5 out of 5
    2 Customer reviews
  • Greve in Chianti, Chianti

    Holiday home for max. 8 persons

    Property no. 1580502
    Approx. 170 m², 4 bedrooms, 4 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher,
  • Castellina in Chianti, Chianti

    Holiday home for max. 12 persons

    Property no. 1633906
    Approx. 267 m², 6 bedrooms, 6 bathrooms, pets are allowed (max. 2), TV, Internet, Wifi, washing machine, ,
  • Greve in Chianti, Chianti

    Holiday home for max. 11 persons

    Property no. 2319893
    Approx. 500 m², 6 bedrooms, 6 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher,
  • Greve in Chianti, Chianti

    Holiday home for max. 23 persons

    Property no. 2319894
    Approx. 825 m², 12 bedrooms, 12 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher,
  • Bucine, Chianti

    Holiday home for max. 6 persons

    Property no. 2320948
    Approx. 150 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 1), Internet, Wifi, washing machine, dishwasher, non-smoking property,
  • Castellina in Chianti, Chianti

    Holiday home for max. 4 persons

    Property no. 3258672
    Approx. 50 m², 2 bedrooms, 1 bathroom, pets not allowed, TV, Internet, Wifi, dishwasher, non-smoking property, sandy beach approx. m
  • Pergine Valdarno, Chianti

    Holiday home for max. 16 persons

    Property no. 3294721
    Approx. 350 m², 8 bedrooms, 5 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher, ,
  • Pergine Valdarno, Chianti

    Holiday home for max. 12 persons

    Property no. 3294722
    Approx. 250 m², 6 bedrooms, 3 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher, ,
  • Castellina in Chianti, Chianti

    Holiday home for max. 14 persons

    Property no. 3476500
    from USD 3,651
    for 1 week
    Approx. 180 m², 7 bedrooms, 6 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, dishwasher, non-smoking property, sandy beach approx. m, ,
  • Pergine Valdarno, Chianti

    Holiday home for max. 9 persons

    Property no. 3501743
    from USD 1,504
    for 1 week
    Approx. 150 m², 4 bedrooms, 3 bathrooms, pets are allowed (max. 1), Internet, Wifi, washing machine, dishwasher, non-smoking property, ,
  • Pergine Valdarno, Chianti

    Holiday home for max. 8 persons

    Property no. 3501753
    from USD 1,663
    for 1 week
    Approx. 180 m², 4 bedrooms, 3 bathrooms, pets are allowed (max. 2), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property,