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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.


  • Greve in Chianti, Chianti

    Holiday home for max. 20 persons

    Property no. 3501630
    + 1 more
    from USD 3,588
    for 1 week
    Approx. 470 m², 10 bedrooms, 6 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher, sandy beach approx. m,
    There is one further property type with one accommodation for this complex
  • Gavignano, Chianti

    Holiday home for max. 3 persons

    Property no. 350360
    Approx. 30 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1) (from 01/01/2025), satellite TV (from 01/01/2025), Wifi (from 01/01/2025), non-smoking property (from 01/01/2025),
    4.3 out of 5
    3 Customer reviews
  • Castellina in Chianti, Chianti

    Holiday home for max. 8 persons

    Property no. 1611179
    from USD 9,830
    for 1 week
    Approx. 260 m², 4 bedrooms, 3 bathrooms, pets are allowed (max. 2), satellite TV, Internet, washing machine, dishwasher, beach approx. m,
  • Montebenichi, Chianti

    Holiday apartment for max. 3 persons

    Property no. 1300088
    from USD 1,263
    for 1 week
    Approx. 45 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), TV, Internet, washing machine, beach approx. m,
  • Montebenichi, Chianti

    Holiday apartment for max. 3 persons

    Property no. 1300089
    from USD 1,263
    for 1 week
    Approx. 60 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), TV, Internet, washing machine, beach approx. m,
  • Montebenichi, Chianti

    Holiday apartment for max. 3 persons

    Property no. 1300090
    from USD 1,263
    for 1 week
    Approx. 45 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), TV, Internet, washing machine, beach approx. m,
  • Radda in Chianti, Chianti

    Holiday home for max. 4 persons

    Property no. 37102
    + 1 more
    Approx. 55 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine,
    5.0 out of 5
    2 Customer reviews
    There is one further property type with one accommodation for this complex
  • Montebenichi, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1300086
    from USD 1,688
    for 1 week
    Approx. 55 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, washing machine, beach approx. m,
  • Montebenichi, Chianti

    Holiday apartment for max. 3 persons

    Property no. 1300087
    from USD 1,263
    for 1 week
    Approx. 70 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), TV, Internet, washing machine, beach approx. m,
  • Montebenichi, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1300091
    from USD 1,688
    for 1 week
    Approx. 110 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, washing machine, beach approx. m,
  • Montebenichi, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1627787
    from USD 1,688
    for 1 week
    Approx. 60 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, washing machine, beach approx. m,
  • Castellina in Chianti, Chianti

    Holiday apartment for max. 6 persons

    Property no. 1156409
    from USD 1,346
    for 1 week
    Approx. 80 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 2), satellite TV, Internet, beach approx. m,