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.
The Alabaster Breeze
8 guests
4 bedrooms
Cavriglia, Arezzo
Tucked away in a peaceful spot in the Cavriglia countryside and situated on an idyllic working farm, this characterful farmhouse makes the perfect place for a dreamy holiday with family and friends. Inside, you'll find charming decor reminiscent of a quaint country cottage, with original features such as beam ceilings and exposed stonework that make it feel special.
Tuscan Memories
6 guests
3 bedrooms
Gaiole in Chianti, Siena
This rustic stone villa is located just a short stroll from the historic centre of Gaiole, surrounded by world-class vineyards and sun-drenched olive groves. The traditional building has been thoughtfully restored and now boasts contemporary decor alongside many of its original features.
Chianti Belle
8 guests
4 bedrooms
Gaiole in Chianti, Siena
This 17th-century villa in the heart of the Chianti countryside offers far-reaching views across the vineyards and olive groves out to Siena. You're within walking distance of Lecchi, as well as being a fifteen-minute drive from Radda in Chianti for dreamy day trips exploring the region.
Explore the 3726 most perfect homes in our collection
Explore our collection of luxury Extended Stay Rentals available for you to rent in Gaiole in Chianti, Siena, Tuscany, Italy. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Gaiole in Chianti, Siena, Tuscany, Italy collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.
