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 Tuscan Moon
10 guests
5 bedrooms
Castellina in Chianti, Tuscany
Nestled between the pretty hilltop towns of Chianti, this home offers a traditional Italian sanctuary. Enjoy breathtaking views across vineyards while relaxing on the terrace.
The Sun Kingdom
10 guests
5 bedrooms
Tignano, Barberino Tavarnelle
Surrounded by olive and cypress trees, this home is the perfect setting to slow down and savour the magic of Italian living. Spend blissful days relaxing by the pool, sipping drinks on the terrace and dining under the stars.
A Guide to the Hills
9 guests
5 bedrooms
Radda in Chianti, Tuscany
Overlooking the Chianti hills, this home is the ideal setting for a restorative Tuscan getaway. Spread across two floors (connected by external stairs), there are two kitchens, family-friendly rooms and plenty of space for groups to stretch out and enjoy quality time together.
Explore the 636 most perfect homes in our collection
A handpicked selection of the best luxury homes in Castellina in Chianti, Siena, Tuscany, Italy, 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.
