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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. 1699633
    from USD 1,840
    for 1 week

    Greve in Chianti, Chianti

    Holiday home for max. 6 persons

    Approx. 110 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), cable TV, Internet, dishwasher, non-smoking property, sea approx. m,
    4.0 out of 5
    1 Customer review
  • Property no. 466359
    from USD 1,306
    for 1 week

    San Giovanni Valdarno, Chianti

    Holiday apartment for max. 4 persons

    Approx. 65 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Wifi, non-smoking property, beach approx. 90 km, , ,
  • Property no. 648365
    from USD 2,508
    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. 878177
    from USD 1,834
    for 1 week

    Castelnuovo Berardenga, Chianti

    Holiday apartment for max. 5 persons

    Approx. 87 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, washing machine, dishwasher,
  • Property no. 878182
    from USD 1,589
    for 1 week

    Castelnuovo Berardenga, Chianti

    Holiday apartment for max. 4 persons

    Approx. 78 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, dishwasher,
  • Property no. 1179628
    from USD 2,497
    for 1 week

    Greve in Chianti, Chianti

    Holiday home for max. 7 persons

    Approx. 87 m², 3 bedrooms, 3 bathrooms, pets are allowed (on request), Wifi, washing machine, dishwasher, non-smoking property,
  • Property no. 1363098

    Pergine Valdarno, Chianti

    Holiday home for max. 2 persons

    Approx. 69 m², 1 bedroom, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, non-smoking property
  • Property no. 1368892

    Pergine Valdarno, Chianti

    Holiday home for max. 6 persons

    Approx. 130 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property
  • Property no. 1699634
    from USD 1,786
    for 1 week

    Greve in Chianti, Chianti

    Holiday apartment for max. 4 persons

    Approx. 90 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Internet, Wifi, dishwasher, non-smoking property, sea approx. m,
  • Property no. 1699635
    from USD 1,821
    for 1 week

    Greve in Chianti, Chianti

    Holiday home for max. 2 persons

    Approx. 63 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), Internet, dishwasher, non-smoking property, sea approx. m
  • Property no. 1699636
    from USD 1,384
    for 1 week

    Greve in Chianti, Chianti

    Holiday apartment for max. 2 persons

    Approx. 60 m², 1 bedroom, 1 bathroom, pets not allowed, TV, Internet, Wifi, non-smoking property, sea approx. m,
  • Property no. 1923493
    from USD 1,615
    for 1 week

    Bucine, Chianti

    Holiday apartment for max. 4 persons

    Approx. 75 m², 3 bedrooms, 1 bathroom, pets are allowed (max. 1), satellite TV, Wifi,