5-Star Luxury Rentals Gaiole in Chianti

Offering views of the surrounding hills and the owner's vineyard, this eco-friendly villa is set within the Chianti countryside. While the interior is fairly subdued and the unpaved road leading here.....

Nestled in the heart of Italy's Chianti region, this traditional Tuscan farmhouse, which was once a working mill, offers both character and charm. With wooden beams, exposed stone walls, and terracott.....

This marvellous Tuscan villa is perfect for groups eager to sample the unique delights of the Chianti region. Set back from civilisation in the region's rolling hills, up to eight guests can rest comf.....

Housed in a restored stone barn, this cottage places you in the heart of Chianti with views of rolling fields, vineyards and valleys as far as the eye can see. The home benefits from a beautifully ele.....

With stunning views of the valley, this ground-floor apartment in this countryside resort has its own outdoor dining area where you may spot passing deer and other animals. There’s a shared swimming p.....

Cosy, rustic 3-family house "Montechioccioli", surrounded by vineyards. 3 apartments in the property. In the hamlet Rietine 4 km from the centre of Gaiole in Chianti, 12 km from the centre of Radda in.....

Located in a former wine and olive oil estate, this property is rich in rustic stone, sweeping vistas, and tonnes of space for the little ones to run around – not to mention the added bonus of a kids'.....

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.....

Nestled in the heart of Chianti, this charming ground-floor apartment promises a tranquil retreat surrounded by nature. Set on a resort, there are shared facilities such as a communal swimming pool, t.....

Part of a 13th-century estate-turned-resort, this apartment makes the most of its scenic location in Chianti. Alongside a private terrace, you'll have access to a communal hilltop swimming pool, share.....

Nestled in the woods in the uplands of Gaiole, this ground-floor apartment is an ideal base for those keen to escape the hustle and bustle of everyday life. Sure, the traditional style of this home ma.....

Wake up to postcard-perfect views in the heart of Chianti, where this cottage offers a slice of classic Tuscan charm. Stone walls and high, beamed ceilings give a rustic feel, while WiFi and a fully e.....

Surrounded by the rolling vistas of a famous wine estate, this Tuscan villa boasts a spacious private pool, stunning views, and space for alfresco dining. The decor is quite traditional and won't be t.....

This Tuscan cottage can be found amid beautiful gardens with views of the gently rolling hills. The land used to be a vineyard, but has been restored into a resort of cottages and apartments in the st.....

This former defence watchtower dating back to the 10th century has been beautifully reimagined into a corker of a family home. Within the palatial grounds, there's a ping-pong table, pool table, table.....

Nestled in the Chianti hills, this home is surrounded by Tuscan countryside. While the swimming pool here is shared with guests at a neighbouring villa, you’ll have your own terrace to enjoy – perfect.....

You’ll find this apartment in a traditional stone building that was once part of an estate producing wine and olive oil. That heritage means this home is full of rustic character, brought up to date w.....

The detached cottage in the Tuscan hills boasts extensive views and a large aromatic garden with a private plunge pool and covered dining terrace. Situated in Montebuoni, a restored estate that recrea.....

Overlooking vineyards, olive groves, and ancient oak forests, this collection of restored farmhouses offer the ultimate relaxed country retreat. With a refreshingly refurbished interior, saltwater inf.....

With incredible views across the Tuscan countryside, this home sets the tone for a magical Italian getaway. Nestled in the heart of Chianti, you’ll be welcomed by the sweet sounds of nature, a private.....

This studio apartment in a stone barn conversion is a perfect blend of modern and antique design. We love the infinity pool (40 metres away) which overlooks the Val d'Orcia, offering breathtaking view.....

In the quaint village of Lecchi in Chianti, this semi-detached cottage is part of Montebuoni, a Tuscan hamlet with stunning views of Chianti Classico's vineyards. While the little cottage and its priv.....

Once a hay barn, now a romantic retreat for two, this villa has tranquillity running through its core. Set on an estate surrounded by vineyards that produce some of the region’s most prestigious wines.....

To say this luxury handcrafted stone villa took our breath away, well, that's an understatement. This place is enchanting with its vistas over a patchwork of Chianti Classico vineyards, olive groves,.....

Set in a hamlet among vine-covered hills, this home is one of eleven houses, with origins dating back to 1400. There’s a flower and plant-filled private garden and shaded terrace perfect for alfresco.....