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Holiday houses in Chianti & holiday apartments in Chianti

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    From USD 389

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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.

Reviews from our customers

4.4 out of 5 (631 Customer reviews)
1 The holiday homes and apartments in in Chianti have been rated by 631 customers, scoring 4.4 out of 5 houses, on average.

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  • Property no. 842042
    from USD 1,097
    for 1 week

    Tavernelle Val di Pesa, Chianti

    Holiday home for max. 8 persons

    Approx. 160 m², 4 bedrooms, 3 bathrooms, pets are allowed (max. 2), satellite TV, WLAN, washing machine, dishwasher, sea approx. 90 km,
    4.3 out of 5
    7 Customer reviews
  • Property no. 922150
    from USD 764
    for 1 week

    Villa a Sesta, Chianti

    Holiday apartment for max. 5 persons

    2 bedrooms, 1 bathroom, pets not allowed, satellite TV, WLAN, washing machine, dishwasher,
    4.8 out of 5
    4 Customer reviews
  • Property no. 881917
    from USD 2,152
    for 1 week

    Pergine Valdarno, Chianti

    Holiday home for max. 15 persons

    Approx. 290 m², 9 bedrooms, 7 bathrooms, pets are allowed (max. 2), satellite TV, WLAN, washing machine, dishwasher, , ,
    5.0 out of 5
    2 Customer reviews
  • Property no. 644384
    from USD 678
    for 1 week

    San Donato in Poggio, Chianti

    Holiday apartment for max. 4 persons

    Approx. 55 m², 2 bedrooms, 1 bathroom, pets not allowed, satellite TV, Complete WLAN coverage, dishwasher, sea approx. 90 km,
    5.0 out of 5
    1 Customer review
    There are 3 further property types with 3 accommodations for this complex
  • Property no. 695023
    from USD 1,115
    for 1 week

    Poggibonsi, Chianti

    Holiday apartment for max. 6 persons

    2 bedrooms, 1 bathroom, pets are allowed (max. 1), Internet, washing machine, dishwasher, , ,
    4.8 out of 5
    6 Customer reviews
    There is one further property type with one accommodation for this complex
  • Property no. 638076
    from USD 603
    for 1 week

    Gaiole in Chianti, Chianti

    Holiday apartment for max. 5 persons

    Approx. 70 m², 2 bedrooms, 1 bathroom, pets are allowed (on request), satellite TV, Internet, washing machine, ,
    4.3 out of 5
    8 Customer reviews
    There is one further property type with one accommodation for this complex
  • Property no. 655806
    from USD 1,033
    for 1 week

    Gaiole in Chianti, Chianti

    Holiday apartment for max. 9 persons

    Approx. 180 m², 4 bedrooms, 3 bathrooms, pets are allowed (max. 2), satellite TV, Internet, WLAN, washing machine, dishwasher, beach approx. 120 km, ,
    4.2 out of 5
    5 Customer reviews
  • Property no. 939526
    from USD 1,612
    for 1 week

    Poggibonsi, Chianti

    Holiday home for max. 10 persons

    4 bedrooms, 4 bathrooms, pets are allowed (max. 1), satellite TV, washing machine, dishwasher, ,
  • Property no. 477073
    from USD 785
    for 1 week

    Monteriggioni, Chianti

    Holiday apartment for max. 4 persons

    Approx. 60 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 2), beach approx. 80 km, ,
    4.8 out of 5
    4 Customer reviews
    There is one further property type with one accommodation for this complex
  • Property no. 410800
    from USD 715
    for 1 week

    Castellina in Chianti, Chianti

    Holiday home for max. 8 persons

    Approx. 180 m², 4 bedrooms, 3 bathrooms, pets are allowed (max. 1), washing machine, , ,
    4.2 out of 5
    5 Customer reviews
  • Property no. 962124
    from USD 732
    for 1 week

    Bucine, Chianti

    Holiday home for max. 2 persons

    Approx. 45 m², 1 bedroom, 1 bathroom, pets are allowed (on request), satellite TV, Internet, washing machine, sea approx. 150 km,
    5.0 out of 5
    2 Customer reviews
  • Property no. 466428
    from USD 715
    for 1 week

    Figline Valdarno, Chianti

    Holiday apartment for max. 4 persons

    2 bedrooms, 1 bathroom, pets are allowed (max. 1), TV, Complete WLAN coverage, non-smoking property, sandy beach approx. 90 km, , , ,
    5.0 out of 5
    2 Customer reviews
    There are 3 further property types with 3 accommodations for this complex
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