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Holiday houses & apartments in Chianti

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Relaxed vacation at a holiday home in Chianti

Whether it be a cozy holiday apartment in an old-fashioned village, a picturesque rural holiday house surrounded by lush green meadows and age-old farmhouses, or a bed and breakfast in a villa, there are many holiday rentals to suit your needs in Chianti. Centrally located between Siena and Florence, Chianti is a great place to base yourself and a day trip in the surrounding areas is quick and easy. It is famous for its vineyards and wineries, which produce some of the world's most popular red wines.

Tips for a vacation in Chianti

In Chianti, you can look forward to driving down winding roads to enjoy the view of the vineyards over the hills or stopping to visit wine cellars and taste great red wines. Hilltop villages, many with medieval churches and buildings still standing, offer a charming backdrop for your holiday in Chianti. Go beyond the olive groves and vineyards of Chianti to enjoy the various activities and events that take place throughout the year. The area’s food festivals, sporting events and rock concerts are great fun for the entire family. If you love contemporary art and spending time outdoors, don't forget to visit the beautiful Chianti Sculpture Park, which is set in the woods between Vagliagli and Pievasciata. Although you might think that Chianti is all about wine, there are many fun family activities in Chianti that don’t necessarily involve wine, unless you want them to. Popular attractions for the whole family include the Multifunctional observatory of the Chianti, the Archeological Museum of Chianti Senese and la Rocca di Staggia castle.

Why book a holiday home in Chianti through TUIvillas.com?

TUIvillas.com offers a trustworthy and competent platform for renting a holiday home in Chianti. TUIvillas.com is a reliable source for not only luxury holiday houses but budget-friendly holiday rentals as well.


  • Sorting:
  • Property no. 922150

    Villa a Sesta, Chianti

    Holiday apartment for max. 5 persons

    4.6 out of 5 (7 Customer reviews)
    from USD 827
    for 1 week
    Approx. 130 m², 2 bedrooms, 1 bathroom, pets not allowed, satellite TV, WLAN, washing machine, dishwasher,
  • Property no. 271861
    + 2 more

    Castellina in Chianti, Chianti

    Studio for max. 2 persons

    4.9 out of 5 (9 Customer reviews)
    from USD 440
    for 1 week
    Approx. 45 m², 1 bathroom, pets are allowed (max. 1), satellite TV, Internet, WLAN, dishwasher, non-smoking property,
    There are 2 further property types with 2 accommodations for this complex
  • Holiday apartment 1156406 for 6 persons in Castellina in Chianti NEW
    Property no. 1156406

    Castellina in Chianti, Chianti

    Holiday apartment for max. 6 persons

    from USD 969
    for 1 week
    Approx. 95 m², 2 bedrooms, pets are allowed (max. 2), satellite TV, Internet, beach approx. 121 km,
  • Holiday apartment 1156410 for 6 persons in Castellina in Chianti NEW
    Property no. 1156410

    Castellina in Chianti, Chianti

    Holiday apartment for max. 6 persons

    from USD 1,283
    for 1 week
    Approx. 140 m², 2 bedrooms, pets are allowed (max. 2), satellite TV, Internet, dishwasher, beach approx. 121 km,
  • Holiday apartment 1300087 for 4 persons in Bucine NEW
    Property no. 1300087

    Bucine, Chianti

    Holiday apartment for max. 4 persons

    from USD 671
    for 1 week
    Approx. 70 m², 1 bedroom, pets are allowed (max. 2), TV, washing machine, beach approx. 140 km,
  • Holiday apartment 1300089 for 3 persons in Bucine NEW
    Property no. 1300089

    Bucine, Chianti

    Holiday apartment for max. 3 persons

    from USD 671
    for 1 week
    Approx. 60 m², 1 bedroom, pets are allowed (max. 2), TV, washing machine, beach approx. 140 km,
  • Property no. 275328
    + 1 more

    Montevarchi, Chianti

    Holiday apartment for max. 4 persons

    5.0 out of 5 (7 Customer reviews)
    from USD 403
    for 1 week
    Approx. 40 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), satellite TV, Internet, WLAN, washing machine,
    There is one further property type with one accommodation for this complex
  • Property no. 833104
    + 3 more

    Poggibonsi, Chianti

    Holiday apartment for max. 4 persons

    5.0 out of 5 (5 Customer reviews)
    from USD 530
    for 1 week
    Approx. 54 m², 2 bedrooms, 2 bathrooms, pets not allowed, satellite TV, WLAN, sea approx. 90 km, ,
    There are 3 further property types with 3 accommodations for this complex
  • Property no. 487860
    + 3 more

    Barberino Val d'Elsa, Chianti

    Holiday apartment for max. 5 persons

    5.0 out of 5 (1 Customer review)
    from USD 497
    for 1 week
    Approx. 65 m², 2 bedrooms, 1 bathroom, pets are allowed (on request), satellite TV, Complete WLAN coverage, washing machine, dishwasher, sea approx. 80 km,
    There are 3 further property types with 3 accommodations for this complex
  • Property no. 636453
    + 5 more

    San Polo in Chianti, Chianti

    Holiday apartment for max. 8 adults + 1 child

    from USD 960
    for 1 week
    Approx. 80 m², 4 bedrooms, 2 bathrooms, pets are allowed (on request), satellite TV, Complete WLAN coverage, dishwasher,
    There are 5 further property types with 5 accommodations for this complex
    more
  • Property no. 969968
    + 1 more

    Gaiole in Chianti, Chianti

    Holiday home for max. 2 persons

    5.0 out of 5 (1 Customer review)
    from USD 640
    for 1 week
    Approx. 72 m², 1 bedroom, 1 bathroom, pets not allowed, satellite TV, Complete WLAN coverage, non-smoking property, sea approx. 100 km, ,
    There is one further property type with one accommodation for this complex
  • Property no. 871710

    Poggibonsi, Chianti

    Holiday apartment for max. 4 persons

    from USD 1,129
    for 1 week
    3 bedrooms, 1 bathroom, pets not allowed, satellite TV, Internet, washing machine, dishwasher, ,
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The TUI quality algorithm

We scan hundreds of thousands of holiday homes for you and only take on verified providers. But only when a holiday home fulfils our quality and service criteria, will our quality algorithm single it out with the TUI smile.

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Offer to holiday home owners

You have a holiday home or apartment of your own and you want to increase your occupancy rate and reach more customers? TUI Villas will assume the active mediation process and Europe-wide marketing – without any risk for you as the owner.

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