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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.


  • Montevarchi, Chianti

    Holiday home for max. 6 persons

    Property no. 36392
    Approx. 110 m², 3 bedrooms, 3 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher, ,
    5.0 out of 5
    1 Customer review
  • Cavriglia, Chianti

    Holiday home for max. 4 persons

    Property no. 1014797
    from USD 822
    for 1 week
    Approx. 100 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi
    5.0 out of 5
    1 Customer review
  • Greve in Chianti, Chianti

    Holiday home for max. 8 persons

    Property no. 31473
    + 1 more
    Approx. 120 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher
    3.0 out of 5
    1 Customer review
    There is one further property type with one accommodation for this complex
  • Poggibonsi, Chianti

    Holiday home for max. 8 persons

    Property no. 350214
    Approx. 140 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 1) (from 01/01/2025), 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)
  • Vepri, Chianti

    Holiday apartment for max. 5 adults + 2 children

    Property no. 628899
    Approx. 120 m², 4 bedrooms, 3 bathrooms, pets not allowed, satellite TV (from 01/01/2025), Internet (from 01/01/2025), washing machine (from 01/01/2025), dishwasher (from 01/01/2025), non-smoking property (from 01/01/2025),
  • Gaiole in Chianti, Chianti

    Holiday apartment for max. 6 persons

    Property no. 1163189
    Approx. 90 m², 2 bedrooms, 1 bathroom, pets not allowed, satellite TV (from 01/01/2025), Wifi (from 01/01/2025), dishwasher (from 01/01/2025), non-smoking property (from 01/01/2025),
  • Cavriglia, Chianti

    Holiday home for max. 8 persons

    Property no. 3467240
    from USD 1,251
    for 1 week
    Approx. 240 m², 4 bedrooms, 1 bathroom, pets are allowed (max. 2) (from 01/01/2025), cable TV (from 01/01/2025), Wifi (from 01/01/2025), non-smoking property (from 01/01/2025),
  • Casastieri, Chianti

    Holiday home for max. 4 persons

    Property no. 1241021
    from USD 1,380
    for 1 week
    Approx. 70 m², 2 bedrooms, 2 bathrooms, pets not allowed, Wifi (from 01/01/2025), washing machine (from 01/01/2025), dishwasher (from 01/01/2025), non-smoking property (from 01/01/2025),
    5.0 out of 5
    1 Customer review
  • Greve in Chianti, Chianti

    Holiday home for max. 8 persons

    Property no. 1580502
    Approx. 170 m², 4 bedrooms, 4 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher,
  • Greve in Chianti, Chianti

    Holiday home for max. 11 persons

    Property no. 2319893
    Approx. 500 m², 6 bedrooms, 6 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher,
  • Greve in Chianti, Chianti

    Holiday home for max. 23 persons

    Property no. 2319894
    Approx. 825 m², 12 bedrooms, 12 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher,
  • Pergine Valdarno, Chianti

    Holiday home for max. 12 persons

    Property no. 3294722
    Approx. 250 m², 6 bedrooms, 3 bathrooms, pets not allowed, TV, Internet, Wifi, washing machine, dishwasher, ,