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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.


  • Castelnuovo Berardenga, Chianti

    Holiday apartment for max. 4 persons

    Property no. 878182
    from USD 1,781
    for 1 week
    Approx. 78 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, dishwasher,
  • San Casciano in Val di Pesa, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1025954
    + 5 more
    from USD 2,344
    for 1 week
    Approx. 40 m², 1 bedroom, 1 bathroom, pets not allowed, satellite TV, Wifi, dishwasher, non-smoking property, sandy beach approx. 110 km, , , , ,
  • Pergine Valdarno, Chianti

    Holiday home for max. 4 persons

    Property no. 1363099
    Approx. 80 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), Internet, Wifi, washing machine, dishwasher
  • Pergine Valdarno, Chianti

    Holiday home for max. 6 persons

    Property no. 1368892
    Approx. 130 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property
  • Greve in Chianti, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1699634
    from USD 1,531
    for 1 week
    Approx. 90 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Wifi, dishwasher, non-smoking property, sea approx. 80 km,
  • Greve in Chianti, Chianti

    Holiday home for max. 2 persons

    Property no. 1699635
    from USD 1,531
    for 1 week
    Approx. 63 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), dishwasher, non-smoking property, sea approx. 100 km
  • Greve in Chianti, Chianti

    Holiday apartment for max. 2 persons

    Property no. 1699636
    from USD 1,192
    for 1 week
    Approx. 60 m², 1 bedroom, 1 bathroom, pets not allowed, TV, Wifi, non-smoking property, sea approx. 100 km,
  • Castellina in Chianti, Chianti

    Holiday home for max. 2 persons

    Property no. 3468586
    from USD 1,015
    for 1 week
    1 bedroom, 1 bathroom, pets are allowed (max. 1), Internet, Wifi, dishwasher,
  • Lilliano, Chianti

    Holiday home for max. 6 persons

    Property no. 3501585
    + 2 more
    from USD 907
    for 1 week
    Approx. 75 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property, sandy beach approx. m,
    There are 2 further property types with 2 accommodations for this complex
  • Castellina in Chianti, Chianti

    Holiday apartment for max. 4 persons

    Property no. 264413
    + 2 more
    Approx. 85 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine,
    5.0 out of 5
    6 Customer reviews
    There are 2 further property types with 2 accommodations for this complex
  • Figline Valdarno, Chianti

    Studio for max. 2 persons

    Property no. 1393127
    from USD 1,021
    for 1 week
    Approx. 45 m², 1 bathroom, pets are allowed (max. 1), TV, Wifi, beach approx. 90 km, , , ,
  • Prumiano, Chianti

    Holiday apartment for max. 4 persons

    Property no. 3242151
    from USD 1,577
    for 1 week
    Approx. 65 m², 2 bedrooms, 2 bathrooms, pets not allowed, non-smoking property, beach approx. 80.0 km, sea approx. 100 km, , , , , ,