5-Star Luxury Rentals Radda in Chianti

We immediately fell in love with the view from the swimming pool at this villa tucked into the Chianti hills. Nothing but green hills as far as the eye can see. The grounds are kept blissfully private.....

This former lookout tower once guarded the passage between Florence and Siena. Today, it exists as a calm sanctuary offering idyllic views, a private pool and serene grounds. The rooms are spread acro.....

Peace and placidity await you at this authentically Tuscan bungalow. It sits in a serene countryside spot in Radda in Chianti, just a short stroll from some lovely shops and restaurants in the heart o.....

Nestled in the Chianti countryside between Siena and Florence, this home has serenity running through its core. Sat atop a hill, surrounded by olive groves and vineyards (the site is actually an activ.....

This traditional Tuscan home opens its doors to the natural beauty of the Chianti region. Nestled amid the trees, the private garden lends itself perfectly to lazy days by the pool. You’ll also find p.....

Perched on the slopes of the Chianti hills, this stone villa effortlessly blends traditional Tuscan farmhouse charm with modern comforts. Since children under six aren’t permitted here, this villa is.....

Amidst the vineyards of Chianti, this apartment is a peaceful sanctuary where days can be spent lounging by the shared pool or out exploring the region. It’s just a short (albeit steep) walk to the vi.....

You'll find this stone villa in the Chianti countryside. Radda and Castellina are both 5 kilometres away, so you'll be well-positioned to explore the area's vineyards and villages. Florence is also dr.....

Ceperano is a charming Tuscan farmhouse that has been restored to a high standard and can accommodate up to 14 guests. The property is situated in the heart of the Chianti region, surrounded by olive.....

Nestled within the iconic green hills of Tuscany, close to the charming hilltop town of Radda, this beautifully restored farmhouse has everything you need for a good time – delicious food, great wine.....

You’ll find this restored farmhouse in the heart of Chianti, surrounded by vineyards and olive groves. Spread across a main house and a separate cottage, this place is perfect for a group of ten to ge.....

Overlooking the Chianti hills, this home is the ideal setting for a restorative Tuscan getaway. Spread across two floors (connected by external stairs), there are two kitchens, family-friendly rooms a.....

Tucked away in the Tuscan countryside, this idyllic villa promises plenty of rest, relaxation and rustic charm. Famous for its rolling hills, acres of vineyards and quaint, historic hamlets, there's n.....

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.....

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.....

At this rustic villa, rolling vineyards are on your doorstep. We mean that quite literally – the owners are local winemakers, and they offer tastings in the medieval tower-turned-wine bar. They'll als.....

Sit back, relax and soak up the sunshine at this characterful villa in Chianti. It may be a little dated inside, but the twin apartment layout is perfect for families and groups that want their own sp.....

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 geta.....

Overlooking the Tuscan countryside from its hillside position, this rustic villa boasts some incredible views – best celebrated from the outside dining area and elegant infinity pool. We think it's a.....

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. With its two.....