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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.


  • Property no. 1670710
    from USD 1,214
    for 1 week

    Tavarnelle Val di Pesa, Chianti

    Holiday apartment for max. 4 persons

    Approx. 120 m², 2 bedrooms, 2 bathrooms, pets not allowed, satellite TV, Wifi, washing machine, dishwasher, non-smoking property,
  • Property no. 1670711
    from USD 1,126
    for 1 week

    Tavarnelle Val di Pesa, Chianti

    Holiday apartment for max. 4 persons

    Approx. 120 m², 2 bedrooms, 2 bathrooms, pets not allowed, satellite TV, Wifi, washing machine, dishwasher, non-smoking property,
  • Property no. 3444201
    from USD 2,425
    for 1 week

    Pievasciata, Chianti

    Holiday home for max. 10 persons

    Approx. 300 m², 5 bedrooms, 3 bathrooms, pets are allowed (max. 2), satellite TV, Wifi, dishwasher, , , ,
  • Property no. 466429
    from USD 1,021
    for 1 week

    Figline Valdarno, Chianti

    Holiday apartment for max. 2 adults + 2 children

    Approx. 40 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
  • Property no. 636419
    + 4 more
    from USD 643
    for 1 week

    San Polo in Chianti, Chianti

    Holiday apartment for max. 5 persons

    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
  • Property no. 1219451
    from USD 1,515
    for 1 week

    Panzano in Chianti, Chianti

    Holiday home for max. 4 persons

    Approx. 100 m², 2 bedrooms, 2 bathrooms, pets not allowed, satellite TV, washing machine
    5.0 out of 5
    1 Customer review
  • Property no. 3241696
    from USD 790
    for 1 week

    Prumiano, Chianti

    Holiday apartment for max. 2 persons

    Approx. 40 m², 1 bedroom, 1 bathroom, pets not allowed, sea approx. 100 km, , , , ,
    4.0 out of 5
    2 Customer reviews
  • Property no. 1670679

    Tavarnelle Val di Pesa, Chianti

    Holiday apartment for max. 2 persons

    Approx. 60 m², 1 bedroom, 1 bathroom, pets not allowed, satellite TV, Wifi, washing machine, dishwasher, non-smoking property,
  • Property no. 1336334
    from USD 2,946
    for 1 week

    Cavriglia, Chianti

    Holiday home for max. 6 adults + 2 children

    Approx. 250 m², 4 bedrooms, 4 bathrooms, pets are allowed (max. 3), satellite TV, washing machine, dishwasher, sandy beach approx. 130 km, , , ,
    4.0 out of 5
    2 Customer reviews
  • Property no. 1363100

    Pergine Valdarno, Chianti

    Holiday home for max. 6 persons

    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
  • Property no. 1433464
    + 3 more
    from USD 749
    for 1 week

    Terranuova Bracciolini, Chianti

    Holiday apartment for max. 4 persons

    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
  • Property no. 854318
    + 5 more
    from USD 988
    for 1 week

    Rapale, Chianti

    Holiday apartment for max. 6 adults + 2 children

    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