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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.


  • Castellina in Chianti, Chianti

    Holiday home for max. 6 persons

    Property no. 3468587
    from USD 2,332
    for 1 week
    3 bedrooms, 1 bathroom, pets are allowed (max. 1), Internet, Wifi, dishwasher,
  • Poggibonsi, Chianti

    Holiday home for max. 14 persons

    Property no. 493394
    from USD 4,332
    for 1 week
    Approx. 500 m², 7 bedrooms, 7 bathrooms, pets are allowed (any), Wifi, washing machine, dishwasher, ,
  • Bucine, Chianti

    Holiday home for max. 22 persons

    Property no. 877805
    Approx. 550 m², 9 bedrooms, 9 bathrooms, pets are allowed (max. 1), satellite TV, Wifi, washing machine, dishwasher,
    2.0 out of 5
    1 Customer review
  • Castellina in Chianti, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1156405
    from USD 1,019
    for 1 week
    Approx. 50 m², 1 bedroom, 1 bathroom, pets are allowed (max. 2), satellite TV, Internet, beach approx. m,
  • Greve in Chianti, Chianti

    Holiday apartment for max. 3 persons

    Property no. 1361400
    from USD 2,028
    for 1 week
    Approx. 61 m², 1 bedroom, 1 bathroom, pets are allowed (max. 2), satellite TV, Internet, dishwasher, beach approx. m,
  • Terranuova Bracciolini, Chianti

    Holiday home for max. 10 persons

    Property no. 1368893
    Approx. 300 m², 5 bedrooms, 5 bathrooms, pets are allowed (max. 1), TV, Internet, Wifi, washing machine, dishwasher,
  • San Colombano a Bibbione, Chianti

    Holiday apartment for max. 6 persons

    Property no. 3258673
    Approx. 100 m², 3 bedrooms, 1 bathroom, pets are allowed (max. 1), Internet, Wifi, washing machine, dishwasher, non-smoking property, sandy beach approx. m
  • Castellina in Chianti, Chianti

    Holiday home for max. 17 persons

    Property no. 3468583
    from USD 6,727
    for 1 week
    Approx. 20000 m², 8 bedrooms, 5 bathrooms, pets are allowed (max. 1), Internet, Wifi, washing machine, dishwasher,
  • Gavignano, Chianti

    Holiday home for max. 3 persons

    Property no. 350360
    Approx. 30 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1) (from 01/01/2025), satellite TV (from 01/01/2025), Wifi (from 01/01/2025), non-smoking property (from 01/01/2025),
    4.3 out of 5
    3 Customer reviews
  • Pergine Valdarno, Chianti

    Holiday home for max. 7 persons

    Property no. 648365
    from USD 2,508
    for 1 week
    Approx. 215 m², 5 bedrooms, 3 bathrooms, pets not allowed, Wifi, washing machine, dishwasher, non-smoking property,
  • San Casciano in Val di Pesa, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1025954
    + 5 more
    from USD 2,344
    for 1 week
    Approx. 40 m², 1 bedroom, 1 bathroom, pets not allowed, satellite TV, Wifi, dishwasher, non-smoking property, sandy beach approx. 110 km, , , , ,
  • 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