Hillside Harvest
4 guests
2 bedrooms
Gaiole in Chianti, Siena
Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there's a private patio where you can enjoy an alfresco glass of wine.
Tuscan Hilltop
37 guests
18 bedrooms
Greve in Chianti, Florence
If you’re a large group seeking a sun-kissed Italian getaway, look no further than this expansive estate in Greve. Made up of three villas, each with a private pool and separate outdoor space, it’s the perfect blend to allow sociable time gathered as a group and quiet time when needed.
Chianti Memories
10 guests
5 bedrooms
Radda in Chianti, Tuscany
With rolling Chianti hills all around, this traditional villa couldn't feel more Tuscan if it tried. Comprised of a main house and three en-suite bedroom cottages, it's perfect for a large family getaway.
The Tuscan Muse
14 guests
7 bedrooms
Tregole, Tuscany
With majestic views across rolling hills and olive groves, this home makes it easy to enjoy the magic of Italy. Set within a working winery, you’ll be treated to an authentic taste of rural life along with all the essentials you could need to slow down and spend quality time together.
Explore the 3876 most perfect homes in our collection
Book luxury Self-Catering Apartments in Castellina in Chianti, Siena, Tuscany, Italy, and enjoy a memorable stay for all the right reasons. We leave no stone unturned in our pursuit of the most remarkable homes, vetting everything from shower pressure to design aesthetic. Every home in our collection of luxury Castellina in Chianti Self-Catering Rentals comes fully furnished with a well-equipped kitchen, all linens, and essential bathroom toiletries included. And should you need any help in finding the perfect home, our friendly experts are always on hand to help.
