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.
Citrus Pavillion
20 guests
9 bedrooms
Gaiole in Chianti, Siena
Overlooking vineyards, olive groves, and ancient oak forests, this collection of restored farmhouses offer the ultimate relaxed country retreat. With a refreshingly refurbished interior, saltwater infinity pool, bubbly outdoor jacuzzi, private spa and gym, and enough alfresco dining opportunities to shake a stick at, we are positive that this home offers something for each and every guest.
The Italian Dream
10 guests
5 bedrooms
Sarteano, Siena
This swoon-worthy Tuscany villa presents a dreamy fairytale-like setting amidst the quiet, green woodland of Sarteano. Unveiling romantic and characteristic scenery, the home itself is also brimming with charm and personality throughout.
Sixteenth Century
24 guests
12 bedrooms
Campiglia Marittima, Livorno
Perched on a hill overlooking the Tuscan countryside, this 500-year-old Italian castle is kitted out for huge group gatherings, celebrations, and luxurious family get-togethers. It's in the middle of a sprawling estate, flanked by olive trees and grapevines, yet it's only one kilometre from Venturina Terme, so you're not completely out in the sticks.
Explore the 164 most perfect homes in our collection
A handpicked selection of the best luxury homes in Castiglione della Pescaia, 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.
