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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. 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. 969968
    + 1 more
    from USD 640
    for 1 week

    Gaiole in Chianti, Chianti

    Holiday home for max. 2 persons

    Approx. 72 m², 1 bedroom, 1 bathroom, pets not allowed, satellite TV, Complete WLAN coverage, non-smoking property, sea approx. 100 km, ,
    5.0 out of 5
    1 Customer review
    There is one further property type with one accommodation for this complex
  • Property no. 357517
    from USD 466
    for 1 week

    San Casciano in Val di Pesa, Chianti

    Holiday apartment for max. 2 adults + 2 children

    Approx. 70 m², 2 bedrooms, 1 bathroom, pets not allowed, satellite TV, sandy beach approx. 85 km, , ,
    5.0 out of 5
    3 Customer reviews
  • Property no. 1318887
    from USD 781
    for 1 week

    Bucine, Chianti

    Holiday apartment for max. 6 persons

    Approx. 122 m², 3 bedrooms, pets are allowed (max. 2), satellite TV, dishwasher, beach approx. 124 km,
  • Property no. 842886
    from USD 453
    for 1 week

    San Filippo a Ponzano, Chianti

    Holiday apartment for max. 4 persons

    Approx. 50 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), satellite TV, WLAN, ,
    4.0 out of 5
    1 Customer review
  • Property no. 389953
    from USD 757
    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. 56944
    from USD 834
    for 1 week

    Greve in Chianti, Chianti

    Holiday home for max. 6 persons

    Approx. 95 m², 2 bedrooms, 2 bathrooms, pets not allowed, TV, washing machine, dishwasher, , ,
    4.5 out of 5
    2 Customer reviews
  • Property no. 4330
    + 1 more
    from USD 723
    for 1 week

    Greve in Chianti, Chianti

    Holiday apartment for max. 6 persons

    Approx. 65 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), TV, Internet, WLAN, dishwasher,
    5.0 out of 5
    2 Customer reviews
    There is one further property type with one accommodation for this complex
  • Property no. 948000
    from USD 1,895
    for 1 week

    Tavarnelle Val di Pesa, Chianti

    Holiday apartment for max. 6 persons

    3 bedrooms, 2 bathrooms, pets not allowed, washing machine, dishwasher, beach approx. 130 km,
  • Property no. 1148817
    from USD 3,773
    for 1 week

    Montechiaro, Chianti

    Holiday home for max. 10 persons

    5 bedrooms, 4 bathrooms, pets not allowed, washing machine, dishwasher, non-smoking property, ,
  • Property no. 4406
    from USD 1,931
    for 1 week

    San Casciano in Val di Pesa, Chianti

    Holiday home for max. 12 persons

    Approx. 390 m², 6 bedrooms, 6 bathrooms, pets are allowed (max. 1), TV, Internet, washing machine, dishwasher,
    3.5 out of 5
    2 Customer reviews
  • Property no. 922150
    from USD 827
    for 1 week

    Villa a Sesta, Chianti

    Holiday apartment for max. 5 persons

    Approx. 130 m², 2 bedrooms, 1 bathroom, pets not allowed, satellite TV, WLAN, washing machine, dishwasher,
    4.6 out of 5
    7 Customer reviews
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