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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.


  • Rapale, Chianti

    Holiday apartment for max. 6 persons

    Property no. 853848
    + 5 more
    from USD 757
    for 1 week
    Approx. 63 m², 2 bedrooms, 2 bathrooms, pets are allowed (any), satellite TV, Wifi, dishwasher, beach approx. 100 km,
    There are 5 further property types with 5 accommodations for this complex
    show more
  • Rapale, Chianti

    Holiday home for max. 4 persons

    Property no. 854321
    from USD 632
    for 1 week
    Approx. 53 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 10), satellite TV, Wifi, washing machine, dishwasher, sandy beach approx. 100 km, , ,
  • San Gusmè, Chianti

    Holiday apartment for max. 2 persons

    Property no. 877853
    from USD 1,292
    for 1 week
    Approx. 100 m², 1 bedroom, 2 bathrooms, pets are allowed (max. 1), satellite TV, Wifi, dishwasher,
  • Castelnuovo Berardenga, Chianti

    Holiday apartment for max. 2 persons

    Property no. 878175
    from USD 1,205
    for 1 week
    Approx. 68 m², 1 bedroom, 2 bathrooms, pets are allowed (max. 1), satellite TV, dishwasher,
  • Castelnuovo Berardenga, Chianti

    Holiday apartment for max. 2 persons

    Property no. 878179
    from USD 1,205
    for 1 week
    Approx. 57 m², 1 bedroom, 2 bathrooms, pets are allowed (max. 1), satellite TV, dishwasher,
  • Cortine, Chianti

    Holiday apartment for max. 2 persons

    Property no. 1323234
    from USD 1,205
    for 1 week
    Approx. 40 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), satellite TV, Wifi, dishwasher,
  • Pergine Valdarno, Chianti

    Holiday home for max. 4 persons

    Property no. 1363099
    Approx. 80 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), Internet, Wifi, washing machine, dishwasher
  • Pergine Valdarno, Chianti

    Holiday home for max. 6 persons

    Property no. 1368892
    Approx. 130 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher, non-smoking property
  • Greve in Chianti, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1699634
    from USD 1,717
    for 1 week
    Approx. 90 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Internet, Wifi, dishwasher, non-smoking property, sea approx. m,
  • Greve in Chianti, Chianti

    Holiday home for max. 2 persons

    Property no. 1699635
    from USD 1,752
    for 1 week
    Approx. 63 m², 1 bedroom, 1 bathroom, pets are allowed (on request), Internet, dishwasher, non-smoking property, sea approx. m
  • Bucine, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1923490
    from USD 1,652
    for 1 week
    Approx. 75 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, Wifi,
  • Pietraviva, Chianti

    Holiday home for max. 6 persons

    Property no. 2317468
    from USD 3,439
    for 1 week
    Approx. 160 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, Wifi, washing machine, dishwasher, non-smoking property, ,