
The rolling hills, fertile valleys, vineyards, old estates, palaces, ancient villages and incredible cuisine of Chianti all make for a perfect holiday destination. It is a scenic place where you can potentially do it all – make day trips to famous cities like Florence and Pisa, explore endless villas and churches, visit famous wineries, go hiking, cycling, horseback riding and more – or do nothing at all and simply relax. Whether you like to unwind by a pool with a good book or through cultural pursuits or on adrenaline-pumping adventures, you'll find it all.
But what is the most important part of planning a trip to Chianti? Finding the perfect villa in which to rest and from which to enjoy your holiday, of course! So, to help you out, we rounded up some of our most idyllic, typically Tuscan, charming and perfect vacation rentals in Chianti.
But what is the most important part of planning a trip to Chianti? Finding the perfect villa in which to rest and from which to enjoy your holiday, of course! So, to help you out, we rounded up some of our most idyllic, typically Tuscan, charming and perfect vacation rentals in Chianti.

1. Villa Casanova (No longer available)
Villa Casanova is a stone Tuscan farmhouse dating to the 1800s located in the Chianti Classico countryside, a short distance from the town of Castelnuovo Berardenga. Set amongst vineyards and olive groves that grow flush against this 9 bedroom, 10 bath property, it boasts stunning views across the surrounding landscape. With typical and highly finished interiors that are luxurious and cosy, the house features floors in handmade Florentine red brick and exposed-beam ceilings. Elegance, tradition, comfort and modern luxuries all come together in this exceptional rental villa.
Villa Casanova is a stone Tuscan farmhouse dating to the 1800s located in the Chianti Classico countryside, a short distance from the town of Castelnuovo Berardenga. Set amongst vineyards and olive groves that grow flush against this 9 bedroom, 10 bath property, it boasts stunning views across the surrounding landscape. With typical and highly finished interiors that are luxurious and cosy, the house features floors in handmade Florentine red brick and exposed-beam ceilings. Elegance, tradition, comfort and modern luxuries all come together in this exceptional rental villa.

There are two buildings: the main house, where the bedrooms are located, and a second building furnished and organised as a large veranda and dining area for breakfast, lunch, and dinner. Each of the tastefully-appointed guest rooms has a private bath, satellite TV, minibar, air-conditioning, and WIFI. On the grounds there is a private swimming pool (open from the first of May to the end of October), a terrace with sun beds and comfortable chairs by famous Italian design brand EMU and a cottage that acts as a wellness centre and boasts a jacuzzi, sauna, gym and two bathrooms with showers. Special services offered by the owners, at extra cost, include breakfast, lunch and dinners with a private chef, cooking classes and tours of the area.

Absolute luxury, this gem is ideal for weddings and large family or friend groups.
If this incredible property is not within budget or doesn't suit your needs, never fear! For more of our picks of Chianti gems at different price points and of different varieties, just read on to the rest of this series.
If this incredible property is not within budget or doesn't suit your needs, never fear! For more of our picks of Chianti gems at different price points and of different varieties, just read on to the rest of this series.