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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.


  • Property no. 648365
    from USD 4,042
    for 1 week

    Pergine Valdarno, Chianti

    Holiday home for max. 7 persons

    Approx. 215 m², 5 bedrooms, 3 bathrooms, pets not allowed, Wifi, washing machine, dishwasher, non-smoking property,
  • Property no. 853848
    + 5 more
    from USD 988
    for 1 week

    Rapale, Chianti

    Holiday apartment for max. 6 persons

    Approx. 63 m², 2 bedrooms, 2 bathrooms, pets are allowed (any), satellite TV, Wifi, dishwasher, beach approx. 100 km,
    There are 5 further property types with 5 accommodations for this complex
    show more
  • Property no. 854321
    from USD 909
    for 1 week

    Rapale, Chianti

    Holiday home for max. 4 persons

    Approx. 53 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 10), satellite TV, Wifi, washing machine, dishwasher, sandy beach approx. 100 km, , ,
  • Property no. 877834

    Castelnuovo Berardenga, Chianti

    Holiday apartment for max. 2 persons

    Approx. 38 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), Wifi, dishwasher,
  • Property no. 1363099

    Pergine Valdarno, Chianti

    Holiday home for max. 4 persons

    Approx. 80 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), Internet, Wifi, washing machine, dishwasher
  • Property no. 2317468
    from USD 3,670
    for 1 week

    Pietraviva, Chianti

    Holiday home for max. 8 persons

    Approx. 160 m², 5 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, Wifi, washing machine, dishwasher, non-smoking property, , ,
  • Property no. 3251807

    Pergine Valdarno, Chianti

    Holiday home for max. 6 persons

    3 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property,
  • Property no. 3501692
    from USD 902
    for 1 week

    Cavriglia, Chianti

    Holiday home for max. 8 persons

    Approx. 230 m², 4 bedrooms, 2 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher, non-smoking property,
  • Property no. 3241696
    from USD 870
    for 1 week

    Prumiano, Chianti

    Holiday apartment for max. 2 persons

    Approx. 40 m², 1 bedroom, 1 bathroom, pets not allowed, sea approx. 100 km, , , , ,
    4.0 out of 5
    2 Customer reviews
  • Property no. 1368893

    Terranuova Bracciolini, Chianti

    Holiday home for max. 10 persons

    Approx. 300 m², 5 bedrooms, 5 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher,
  • Property no. 1672215
    from USD 870
    for 1 week

    Barberino Val d'Elsa, Chianti

    Holiday apartment for max. 2 persons

    Approx. 40 m², 1 bedroom, 1 bathroom, pets not allowed, , , ,
    4.0 out of 5
    1 Customer review
  • Property no. 1670698
    from USD 1,094
    for 1 week

    Pievasciata, Chianti

    Holiday home for max. 4 persons

    Approx. 100 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 2), TV, Wifi, dishwasher, non-smoking property, sea approx. 80 km,
    5.0 out of 5
    1 Customer review