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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.


  • 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,
  • Gavignano, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1643397
    from USD 1,004
    for 1 week
    Approx. 60 m², 2 bedrooms, 1 bathroom, pets are allowed (on request), TV, Wifi, washing machine, ,
  • Pievasciata, Chianti

    Holiday apartment for max. 6 persons

    Property no. 1670699
    from USD 1,409
    for 1 week
    Approx. 200 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 2), satellite TV, Wifi, dishwasher, non-smoking property, sea approx. 90 km, , ,
  • Gavignano, Chianti

    Holiday apartment for max. 2 adults + 1 child

    Property no. 2232510
    from USD 790
    for 1 week
    Approx. 40 m², 1 bedroom, 1 bathroom, pets not allowed, Wifi, sandy beach approx. 50 km
  • Prumiano, Chianti

    Holiday apartment for max. 2 persons

    Property no. 3242144
    from USD 735
    for 1 week
    Approx. 40 m², 2 bedrooms, 1 bathroom, pets not allowed, sea approx. 100 km, , , , ,
  • Prumiano, Chianti

    Holiday apartment for max. 4 persons

    Property no. 3242151
    from USD 1,577
    for 1 week
    Approx. 65 m², 2 bedrooms, 2 bathrooms, pets not allowed, non-smoking property, beach approx. 80.0 km, sea approx. 100 km, , , , , ,
  • Gavignano, Chianti

    Holiday home for max. 3 persons

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

    Holiday apartment for max. 2 persons

    Property no. 2202847
    from USD 751
    for 1 week
    Approx. 40 m², 1 bedroom, 1 bathroom, pets not allowed, satellite TV, Wifi, sandy beach approx. 35 km
  • Montevarchi, Chianti

    Holiday apartment for max. 2 persons

    Property no. 608084
    + 6 more
    Approx. 49 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), satellite TV, Wifi, dishwasher, non-smoking property, sea approx. 100 km, ,
    5.0 out of 5
    1 Customer review
    There are 6 further property types with 6 accommodations for this complex
    show more
  • San Gusmè, Chianti

    Holiday apartment for max. 4 persons

    Property no. 877854
    from USD 1,911
    for 1 week
    Approx. 100 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, Wifi, dishwasher,
  • Cortine, Chianti

    Holiday apartment for max. 2 persons

    Property no. 1323234
    Approx. 40 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), satellite TV, Wifi, dishwasher,
  • Cortine, Chianti

    Holiday apartment for max. 4 persons

    Property no. 1323235
    Approx. 60 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 1), satellite TV, Wifi, dishwasher,