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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.


  • Figline Valdarno, Chianti

    Holiday home for max. 6 persons

    Property no. 1135616
    from USD 898
    for 1 week
    Approx. 95 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, Wifi, dishwasher, ,
  • Pergine Valdarno, Chianti

    Holiday home for max. 6 persons

    Property no. 1140306
    from USD 874
    for 1 week
    Approx. 80 m², 3 bedrooms, 2 bathrooms, pets are allowed (on request), satellite TV, Internet, Wifi, washing machine, dishwasher, ,
  • Montegonzi, Chianti

    Holiday home for max. 16 persons

    Property no. 2118241
    from USD 2,746
    for 1 week
    Approx. 310 m², 10 bedrooms, 8 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, ,
  • Barberino Val d'Elsa, Chianti

    Holiday apartment for max. 4 persons

    Property no. 472737
    + 3 more
    from USD 646
    for 1 week
    Approx. 70 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), satellite TV, Complete Wifi coverage, washing machine, dishwasher, sea approx. 80 km, ,
    There are 3 further property types with 3 accommodations for this complex
  • Gaiole in Chianti, Chianti

    Holiday home for max. 2 persons

    Property no. 969968
    + 1 more
    from USD 1,068
    for 1 week
    Approx. 72 m², 1 bedroom, 1 bathroom, pets not allowed, satellite TV, Complete Wifi coverage, sea approx. 100 km, , , , ,
    5.0 out of 5
    6 Customer reviews
    There is one further property type with one accommodation for this complex
  • Tavarnelle Val di Pesa, Chianti

    Holiday home for max. 10 persons

    Property no. 1285196
    from USD 2,399
    for 1 week
    Approx. 250 m², 5 bedrooms, 5 bathrooms, pets are allowed (on request), Complete Wifi coverage, washing machine, dishwasher, ,
    4.0 out of 5
    1 Customer review
  • Impruneta, Chianti

    Holiday home for max. 5 persons

    Property no. 618609
    from USD 1,102
    for 1 week
    Approx. 105 m², 3 bedrooms, 2 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher, non-smoking property, , ,
    4.3 out of 5
    3 Customer reviews
  • Castellina Scalo, Chianti

    Holiday apartment for max. 4 persons

    Property no. 264413
    + 2 more
    from USD 631
    for 1 week
    Approx. 85 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, , ,
    5.0 out of 5
    4 Customer reviews
    There are 2 further property types with 2 accommodations for this complex
  • Montevarchi, Chianti

    Holiday apartment for max. 2 persons

    Property no. 608083
    + 5 more
    from USD 1,543
    for 1 week
    Approx. 55 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), satellite TV, Complete Wifi coverage, dishwasher, non-smoking property, sea approx. 100 km, , , , ,
    5.0 out of 5
    2 Customer reviews
    There are 5 further property types with 5 accommodations for this complex
    show more
  • Barberino Val d'Elsa, Chianti

    Holiday apartment for max. 4 persons

    Property no. 494187
    + 1 more
    from USD 1,194
    for 1 week
    Approx. 70 m², 2 bedrooms, 2 bathrooms, pets not allowed, Complete Wifi coverage, washing machine, non-smoking property, , , ,
    5.0 out of 5
    1 Customer review
    There is one further property type with one accommodation for this complex
  • Radda in Chianti, Chianti

    Holiday home for max. 8 persons

    Property no. 276253
    from USD 802
    for 1 week
    Approx. 230 m², 4 bedrooms, 2 bathrooms, pets not allowed, TV, washing machine, dishwasher, non-smoking property, ,
    5.0 out of 5
    2 Customer reviews
  • Mercatale in Val di Pesa, Chianti

    Holiday home for max. 10 persons

    Property no. 22811
    from USD 1,609
    for 1 week
    Approx. 200 m², 5 bedrooms, 4 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, , ,
    4.0 out of 5
    1 Customer review