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.
Into the Olive Grove
10 guests
5 bedrooms
San Filippo a Ponzano, Barberino Tavarnelle
Conveniently located in San Filippo a Ponzano, a rural village on a hill in Chianti, from here you'll be within easy reach of Florence (a forty-five-minute drive away) and Siena (a thirty-minute drive away). Prepare to be blown away by the never-ending landscapes amidst fields of oak woods, vineyards, and olive groves upon arrival.
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.
A Touch of Chianti
8 guests
4 bedrooms
Castellina in Chianti, Tuscany
Stylishly rustic, this country home sets the tone for a restorative retreat in the heart of Chianti. Dating back to the 10th century, the house has a wonderful sense of character with plenty of space for groups to relax and enjoy the garden views.
Explore the 1834 most perfect homes in our collection
Secure a luxury stay in one of the remarkable Villas in our Castellina in Chianti, Siena, Tuscany, Italy collection. Our quality and consistency is unmatched, with only the top 3% of homes making it onto our site. Our meticulous home experts test everything from shower pressure to a home's feel and atmosphere, so there really is no need to worry about a thing. Your chosen home is also guaranteed to be fully furnished, with an excellently-equipped kitchen, essential bathroom toiletries, and linens all included. Acquire the help of our friendly experts, on standby 24/7 and always eager to assist you in your hunt for the finest luxury Villa in the entirety of Castellina in Chianti.
