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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 apartment for max. 4 persons

    Property no. 466423
    from USD 1,306
    for 1 week
    Approx. 65 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Wifi, washing machine, non-smoking property, beach approx. 90 km, , ,
    5.0 out of 5
    1 Customer review
  • Brollo, Chianti

    Holiday apartment for max. 4 persons

    Property no. 466428
    from USD 1,100
    for 1 week
    Approx. 55 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 3), TV, Wifi, non-smoking property, sandy beach approx. 90 km, , , ,
    5.0 out of 5
    2 Customer reviews
  • Figline Valdarno, Chianti

    Holiday apartment for max. 2 adults + 2 children

    Property no. 466429
    from USD 1,021
    for 1 week
    Approx. 44 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Wifi, sandy beach approx. 90 km, , ,
    5.0 out of 5
    1 Customer review
  • San Polo in Chianti, Chianti

    Holiday apartment for max. 5 persons

    Property no. 636419
    + 4 more
    from USD 643
    for 1 week
    Approx. 55 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), satellite TV,
    5.0 out of 5
    1 Customer review
    There are 4 further property types with 4 accommodations for this complex
    show more
  • Panzano in Chianti, Chianti

    Holiday home for max. 4 persons

    Property no. 1219451
    from USD 1,515
    for 1 week
    Approx. 100 m², 2 bedrooms, 2 bathrooms, pets not allowed, satellite TV, washing machine
    5.0 out of 5
    1 Customer review
  • Pergine Valdarno, Chianti

    Holiday home for max. 6 persons

    Property no. 1363100
    Approx. 130 m², 3 bedrooms, 4 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher,
    4.0 out of 5
    1 Customer review
  • Terranuova Bracciolini, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1433464
    + 3 more
    from USD 749
    for 1 week
    Approx. 100 m², 2 bedrooms, 1 bathroom, pets not allowed, TV, Wifi, non-smoking property, , , ,
    5.0 out of 5
    1 Customer review
    There are 3 further property types with 3 accommodations for this complex
  • Greve in Chianti, Chianti

    Holiday home for max. 6 persons

    Property no. 1699633
    from USD 1,696
    for 1 week
    Approx. 110 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), cable TV, dishwasher, non-smoking property, sea approx. 100 km,
    4.0 out of 5
    1 Customer review
  • San Giovanni Valdarno, Chianti

    Holiday apartment for max. 4 persons

    Property no. 466359
    from USD 1,306
    for 1 week
    Approx. 69 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Wifi, non-smoking property, beach approx. 90 km, , ,
  • Pergine Valdarno, Chianti

    Holiday home for max. 7 persons

    Property no. 648365
    from USD 4,042
    for 1 week
    Approx. 215 m², 5 bedrooms, 3 bathrooms, pets not allowed, Wifi, washing machine, dishwasher, non-smoking property,
  • Rapale, Chianti

    Holiday apartment for max. 6 adults + 2 children

    Property no. 854318
    + 5 more
    from USD 988
    for 1 week
    Approx. 75 m², 2 bedrooms, 2 bathrooms, pets not allowed, satellite TV, Wifi, dishwasher,
    There are 5 further property types with 5 accommodations for this complex
    show more
  • Castelnuovo Berardenga, Chianti

    Holiday apartment for max. 2 persons

    Property no. 877834
    Approx. 38 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), Wifi, dishwasher,