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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. 493977
    + 1 more
    from USD 978
    for 1 week

    Barberino Val d'Elsa, Chianti

    Holiday apartment for max. 7 persons

    Approx. 160 m², 4 bedrooms, 3 bathrooms, pets are allowed (on request), cable TV, washing machine, dishwasher, , , ,
    There is one further property type with one accommodation for this complex
  • Property no. 844200
    + 5 more
    from USD 512
    for 1 week

    San Donato in Poggio, Chianti

    Holiday apartment for max. 2 persons

    Approx. 40 m², 1 bedroom, 1 bathroom, pets not allowed, satellite TV, Complete WLAN coverage, dishwasher, sea approx. 90 km,
    5.0 out of 5
    3 Customer reviews
    There are 5 further property types with 5 accommodations for this complex
    show more
  • Property no. 1295343
    from USD 760
    for 1 week

    Pergine Valdarno, Chianti

    Holiday home for max. 7 persons

    Approx. 100 m², 3 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, Internet, WLAN, washing machine, dishwasher,
    5.0 out of 5
    2 Customer reviews
  • Property no. 261343
    + 2 more
    from USD 602
    for 1 week

    Castellina Scalo, Chianti

    Holiday home for max. 4 persons

    Approx. 90 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, WLAN, washing machine,
    5.0 out of 5
    1 Customer review
    There are 2 further property types with 2 accommodations for this complex
  • Property no. 1363100
    from USD 2,792
    for 1 week

    Pergine Valdarno, Chianti

    Holiday home for max. 6 persons

    Approx. 130 m², 3 bedrooms, 4 bathrooms, pets are allowed (max. 1), satellite TV, Internet, WLAN, washing machine, dishwasher,
  • Property no. 1363104
    from USD 1,781
    for 1 week

    Terranuova Bracciolini, Chianti

    Holiday home for max. 10 persons

    5 bedrooms, 5 bathrooms, pets are allowed (max. 1), Internet, WLAN, washing machine, dishwasher, non-smoking property,
  • Property no. 1300088
    from USD 679
    for 1 week

    Bucine, Chianti

    Holiday apartment for max. 4 persons

    Approx. 45 m², 1 bedroom, pets are allowed (max. 2), TV, washing machine, beach approx. 140 km,
  • Property no. 1300091
    from USD 836
    for 1 week

    Bucine, Chianti

    Holiday apartment for max. 6 persons

    Approx. 110 m², 2 bedrooms, pets are allowed (max. 2), TV, Internet, washing machine, beach approx. 140 km,
  • Property no. 389953
    from USD 559
    for 1 week

    Badia a Passignano, Chianti

    Holiday home for max. 6 persons

    Approx. 85 m², 3 bedrooms, 3 bathrooms, pets are allowed (max. 1), TV, Internet, WLAN, washing machine, dishwasher,
  • Property no. 958387
    + 1 more
    from USD 815
    for 1 week

    Barberino Val d'Elsa, Chianti

    Holiday apartment for max. 4 persons

    Approx. 70 m², 2 bedrooms, 1 bathroom, pets are allowed (on request), satellite TV, sandy beach approx. 100 km, , ,
    5.0 out of 5
    2 Customer reviews
    There is one further property type with one accommodation for this complex
  • Property no. 1222558
    from USD 2,075
    for 1 week

    Linari, Chianti

    Holiday home for max. 8 persons

    Approx. 200 m², 3 bedrooms, 3 bathrooms, pets not allowed, satellite TV, Internet, WLAN, washing machine, dishwasher, non-smoking property,
  • Property no. 1363098
    from USD 553
    for 1 week

    Pergine Valdarno, Chianti

    Holiday home for max. 4 persons

    Approx. 65 m², 1 bedroom, 2 bathrooms, pets not allowed, satellite TV, Internet, WLAN, washing machine, non-smoking property
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