The Hilltop Dream
12 guests
6 bedrooms
Radda in Chianti, Tuscany
With breathtaking views across the Chianti countryside, this home will captivate you from the moment of arrival. There’s also a private pool, a peaceful garden and a pergola with a barbecue – perfect for alfresco dining.
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.
Bellissima
16 guests
9 bedrooms
Castellina in Chianti, Tuscany
If you dream of tucking yourself away somewhere in remote Italy, and indulging in nothing but pappardelle pasta, limoncello, and local wines, you’ve come to the right place. This traditional Tuscan home, perched in the idyllic Chianti hills, offers the simple pleasures of rural Italian life.
The Vine Song
8 guests
4 bedrooms
Castelnuovo Berardenga, Siena
Accessible via an unpaved, cypress-lined road and perched on sloping, vineyard-covered hills, this stylish stone villa is Tuscany at its best. Whether you’re here for an intimate wedding or a big family holiday, the place will set your heart pounding.
Explore the 524 most perfect homes in our collection
A handpicked selection of the best luxury homes in Gaiole in Chianti, as chosen by the experts who've visited and vetted thousands of the city's homes. Luxurious interiors, sumptuous bedrooms and prime city centre locations. Available for short and extended stays.
