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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. 3294721

    Pergine Valdarno, Chianti

    Holiday home for max. 16 persons

    Approx. 350 m², 8 bedrooms, 5 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher, ,
  • Property no. 1148663
    + 1 more
    from USD 619
    for 1 week

    Barberino Val d'Elsa, Chianti

    Holiday apartment for max. 4 persons

    Approx. 70 m², 2 bedrooms, 1 bathroom, pets not allowed, TV, Internet, washing machine, dishwasher,
    There is one further property type with one accommodation for this complex
  • Property no. 1391983
    from USD 4,888
    for 1 week

    Castellina in Chianti, Chianti

    Holiday home for max. 16 persons

    Approx. 314 m², 8 bedrooms, 6 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, ,
  • Property no. 1850621
    from USD 1,422
    for 1 week

    Castellina in Chianti, Chianti

    Holiday home for max. 4 persons

    Approx. 80 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, ,
  • Property no. 2118241
    from USD 2,680
    for 1 week

    Montevarchi, Chianti

    Holiday home for max. 16 persons

    Approx. 310 m², 10 bedrooms, 8 bathrooms, pets are allowed (max. 2), TV, Internet, Wifi, washing machine, dishwasher,
  • Property no. 3493581
    from USD 2,614
    for 1 week

    Greve in Chianti, Chianti

    Holiday home for max. 12 persons

    Approx. 160 m², 6 bedrooms, 5 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher,
  • Property no. 3501717
    from USD 654
    for 1 week

    Poggibonsi, Chianti

    Holiday apartment for max. 4 persons

    Approx. 90 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property
  • Property no. 3501810
    + 4 more
    from USD 630
    for 1 week

    San Polo in Chianti, Chianti

    Holiday home for max. 4 persons

    Approx. 65 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 2), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property
    There are 4 further property types with 4 accommodations for this complex
    show more
  • Property no. 351998
    from USD 1,702
    for 1 week

    Lilliano, Chianti

    Holiday home for max. 8 persons

    Approx. 220 m², 4 bedrooms, 3 bathrooms, pets are allowed (max. 2) (from 01/01/2025), satellite TV (from 01/01/2025), Wifi (from 01/01/2025), washing machine (from 01/01/2025), dishwasher (from 01/01/2025), non-smoking property (from 01/01/2025),
  • Property no. 3475864
    from USD 1,885
    for 1 week

    San Casciano in Val di Pesa, Chianti

    Holiday home for max. 9 persons

    Approx. 230 m², 5 bedrooms, 3 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher, non-smoking property, sandy beach approx. m
  • Property no. 3501604
    + 9 more

    Poggibonsi, Chianti

    Holiday home for max. 46 persons

    Approx. 650 m², 18 bedrooms, 13 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property, sandy beach approx. m, ,
    There are 9 further property types with 9 accommodations for this complex
    show more
  • Property no. 3501630
    + 1 more
    from USD 3,588
    for 1 week

    Greve in Chianti, Chianti

    Holiday home for max. 20 persons

    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