The Rosso
8 guests
4 bedrooms
Radda in Chianti, Tuscany
Perched on the slopes of the Chianti hills, this stone villa effortlessly blends traditional Tuscan farmhouse charm with modern comforts. Since children under six aren’t permitted here, this villa is a perfect spot for a group seeking a retreat amongst sprawling gardens.
The Princess of Chianti
6 guests
3 bedrooms
Barbischio, Gaiole in Chianti
This enchanting home in the Chianti region of Tuscany is set on a tiny hamlet near Gaiole and dates back to the 14th century. Offering picturesque views of Chianti woodland and vineyards, dare we say, it feels like somewhere straight out of a fairytale.
Stonehill Vines
6 guests
3 bedrooms
Radda in Chianti, Tuscany
This grand stone villa looks the perfect part in a region known for its Renaissance history and castles. Located on a gentle hillside slope, this 16th century home sings of rural Tuscany.
The Olive Vine
6 guests
3 bedrooms
Gaiole in Chianti, Siena
Just outside of Gaiole's idyllic town, serving authentic cuisine and Chianti wine, this hillside home offers pastoral vistas. There's an upside-down layout inside, putting the bedrooms below the living space, which opens out onto several terraces and a leafy garden with an infinity pool.
Explore the 2928 most perfect homes in our collection
Looking for alternatives to overpriced, cramped hotels in Gaiole in Chianti? You've come to the right place: we’ve cherry-picked a selection of hotel alternatives which offer better value, more space, more privacy and more flexibility. Our vetted homes are located in central, vibrant neighbourhoods. 100% ready for living and available for short or extended stays.
