Mulberry & Olive
6 guests
3 bedrooms
Casanuova di Ama, Gaiole in Chianti
Full of charm, we love this home’s history. It’s hard to imagine its olive press past, save for the very obvious reminder in the living area.
Book Luxury Monthly Rentals in Gaiole in Chianti
We selected the 3156 homes worth renting in this location
Home spotlights in Gaiole in Chianti
The Chianti Essence
8 guests
4 bedrooms
Gaiole in Chianti, Siena
Surrounded by vineyards and olive groves, this charming stone villa welcomes families to explore Chianti. Drive to the lively market town of Gaiole and Brolio Castle, or admire the Tuscan countryside of Castellina in Chianti.
Chianti Classico
12 guests
6 bedrooms
Radda in Chianti, Tuscany
High up in the hills of Chianti sits this magnificent eighteenth-century residence, flanked by olive groves, rose gardens and lemon trees. The sublime archway structures harken back to the traditional Italian palazzo, and the interiors – prizing terracotta tiles and antique furniture – have a distinctly regal feel.
The Olive Vine
6 guests
3 bedrooms
Gaiole in Chianti, Siena
Just outside of Gaiole's idyllic town, serving authentic cuisine and Chianti wine, this hillside home offers pastoral vistas. There's an upside-down layout inside, putting the bedrooms below the living space, which opens out onto several terraces and a leafy garden with an infinity pool.
We selected the top 3% holiday homes in Gaiole in Chianti Monthly Rentals
Explore the 3156 most perfect homes in our collection
View on map
Check upcoming rates & availability for Gaiole in Chianti Monthly Rentals
Frequently asked questions
Discover the ultimate collection of luxury Monthly Rentals in Gaiole in Chianti, Siena, Tuscany, Italy, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Gaiole in Chianti Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.
Search Our Collection