5-Star Luxury Accommodation Gaiole in Chianti

The Olive Vine
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The Olive Vine

Gaiole in Chianti, Tuscany, Italy
From€397
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 livin.....
€397 price from6 guests3 bedrooms
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My Chianti Heart
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My Chianti Heart

Gaiole in Chianti, Tuscany, Italy
From€1,134
Surrounded by vineyards tumbling down hillsides and towering trees, this stone villa sits in the heart of the Chianti Hills. The beautiful village of Lecchi with its ancient castle is just a six-minut.....
€1,134 price from12 guests4 bedrooms
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Chianti Lake
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Chianti Lake

Gaiole in Chianti, Tuscany, Italy
From€267
Tucked away amid the picturesque Chianti Hills, this charming villa offers a peaceful escape. It’s on an agriturismo with five villas and direct access to a beautiful lake where you can swim and sunba.....
€267 price from4 guests2 bedrooms
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From the Hilltop
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From the Hilltop

Gaiole in Chianti, Tuscany, Italy
From€740
This Tuscan villa offers breathtaking views of the surrounding vineyards from its hilltop position. And while the traditional interiors here may not be everyone’s cup of tea, the multiple living space.....
€740 price from6 guests4 bedrooms
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The Tuscan Vine
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The Tuscan Vine

Gaiole in Chianti, Tuscany, Italy
From€1,102
Escape to this Tuscan house that offers a rural setting and traditional features. Located just outside one of Chianti’s oldest hamlets, Vertine, this villa is ideally situated for exploring the quaint.....
€1,102 price from8 guests4 bedrooms
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Chianti Soul
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Chianti Soul

Gaiole in Chianti, Tuscany, Italy
From€585
This restored two-storey stone-built home has a hillside location, so it has wonderful vistas (just don’t bring your sports car as the access road is very steep). You can enjoy the glorious views from.....
€585 price from6 guests3 bedrooms
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Tuscan Memories
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Tuscan Memories

Gaiole in Chianti, Tuscany, Italy
From€507
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 thoughtf.....
€507 price from6 guests3 bedrooms
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Chianti Escape
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Chianti Escape

Gaiole in Chianti, Tuscany, Italy
From€502
Tucked away in the vineyard of a prestigious winery, this elegant cottage overlooks the beautiful Tuscan countryside. But not only are the views from the swimming pool and outdoor seating beautiful, b.....
€502 price from4 guests2 bedrooms
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Chianti Hills
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Chianti Hills

Gaiole in Chianti, Tuscany, Italy
From€1,414
Perched upon a private hilltop in the Chianti hills, the setting of this villa estate is hard to beat. Designed to make the most of those next-level views from all angles, the home has a private pool.....
€1,414 price from12 guests6 bedrooms
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Chianti Blush
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Chianti Blush

Gaiole in Chianti, Tuscany, Italy
From€148
This cottage overlooks Chianti's vine-covered hills, providing an idyllic background for a romantic Tuscan stay. We love the private terrace – there's no better spot to savour a glass of locally-made.....
€148 price from2 guests1 bedroom
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Sunflowers & Sangiovese
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Sunflowers & Sangiovese

Gaiole in Chianti, Tuscany, Italy
From€729
Treat yourself to a relaxing stay at this rustic villa in the heart of Chianti, one of the Old World’s best known wine regions. Fully renovated in 2016, this authentic Italian home will delight even t.....
€729 price from10 guests4 bedrooms
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A Toast to the Tuscan Sun
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A Toast to the Tuscan Sun

Gaiole in Chianti, Tuscany, Italy
From€190
Wrapped in Tuscan countryside, this home is an ideal base for friends or a small family seeking a serene retreat to relax. Dine out under the sun on the private terrace, or head to the communal pool o.....
€190 price from4 guests2 bedrooms
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The Olive Stone
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The Olive Stone

Gaiole in Chianti, Tuscany, Italy
From€895
Enjoying a secluded spot in the Chianti countryside, this traditional stone villa is packed with things to keep you entertained. The gardens are a delight, where olive groves provide a spot for a shad.....
€895 price from6 guests3 bedrooms
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An Ode to Serenity
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An Ode to Serenity

Gaiole in Chianti, Tuscany, Italy
From€382
Surrounded by the Tuscan countryside, this villa suits a small family or two couples looking for a restful escape. Outside, there’s a terrace for relaxing or dining and a hot tub – the perfect place t.....
€382 price from4 guests2 bedrooms
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Ivy & Olive
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Ivy & Olive

Gaiole in Chianti, Tuscany, Italy
From€243
Calling all wine connoisseurs – this villa puts Chianti's vineyards at your fingertips. Whether you're touring local wineries or day-tripping to the towns of Radda and Siena, this is a picture-perfect.....
€243 price from8 guests4 bedrooms
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Oak & Vine
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Oak & Vine

Gaiole in Chianti, Tuscany, Italy
From€171
Surrounded by Chianti countryside, this home has tranquillity running through its core. Ideal for a couple on an Italian getaway, we love the private terrace here – just the spot to enjoy undisturbed.....
€171 price from2 guests1 bedroom
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Toscana Per Sempre
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Toscana Per Sempre

Gaiole in Chianti, Tuscany, Italy
From€162
Housed within a complex of stone buildings that were once a wine and olive oil-producing estate, this home offers Tuscan relaxation in spades. A communal pool, children’s pool and tennis courts await.....
€162 price from2 guests1 bedroom
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Tuscan Idyll
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Tuscan Idyll

Gaiole in Chianti, Tuscany, Italy
From€304
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.....
€304 price from4 guests2 bedrooms
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The Hillside Sanctuary
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The Hillside Sanctuary

Gaiole in Chianti, Tuscany, Italy
From€230
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.....
€230 price from2 guests1 bedroom
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The Chianti Garden
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The Chianti Garden

Gaiole in Chianti, Tuscany, Italy
From€134
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.....
€134 price from2 guests1 bedroom
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Chianti Belle
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Chianti Belle

Gaiole in Chianti, Tuscany, Italy
From€697
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.....
€697 price from8 guests4 bedrooms
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Vino on the Terrace
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Vino on the Terrace

Gaiole in Chianti, Tuscany, Italy
From€182
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.....
€182 price from4 guests2 bedrooms
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Olive & Olive Wood
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Olive & Olive Wood

Gaiole in Chianti, Tuscany, Italy
From€655
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.....
€655 price from8 guests5 bedrooms
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The Chianti Way
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The Chianti Way

Gaiole in Chianti, Tuscany, Italy
From€213
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.....
€213 price from4 guests2 bedrooms
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Sangiovese Sunset
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Sangiovese Sunset

Gaiole in Chianti, Tuscany, Italy
From€164
This semi-detached cottage is wrapped in glorious Chianti countryside, making it an ideal base for a relaxing break for two. We love the private hot tub, nestled in a shady spot and perfect for quiet.....
€164 price from2 guests1 bedroom
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