5-Star Luxury Rentals Gaiole in Chianti

Sangiovese Sunset
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Sangiovese Sunset

Gaiole in Chianti, Tuscany, Italy
From€145
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.....
€145 price from2 guests1 bedroom
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I Dream of Chianti
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I Dream of Chianti

Gaiole in Chianti, Tuscany, Italy
From€840
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.....
€840 price from10 guests5 bedrooms
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Sweet Vine
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Sweet Vine

Gaiole in Chianti, Tuscany, Italy
From€230
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.....
€230 price from4 guests2 bedrooms
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Citrus Pavillion
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Citrus Pavillion

Gaiole in Chianti, Tuscany, Italy
From€1,790
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.....
€1,790 price from20 guests9 bedrooms
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The Chianti Cottage
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The Chianti Cottage

Gaiole in Chianti, Tuscany, Italy
From€356
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.....
€356 price from2 guests1 bedroom
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Tuscan Whisper
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Tuscan Whisper

Gaiole in Chianti, Tuscany, Italy
From€150
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.....
€150 price from2 guests1 bedroom
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Hillside Harvest
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Hillside Harvest

Gaiole in Chianti, Tuscany, Italy
From€229
Nestled on a hilltop estate surrounded by vineyards, this home is one of six on the site of a former medieval castle. You'll share access to the grounds and swimming pool with other guests, but there'.....
€229 price from4 guests2 bedrooms
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The Soul Of Wine
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The Soul Of Wine

Gaiole in Chianti, Tuscany, Italy
From€1,475
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,.....
€1,475 price from14 guests7 bedrooms
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The Olive Dawn
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The Olive Dawn

Gaiole in Chianti, Tuscany, Italy
From€159
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.....
€159 price from4 guests2 bedrooms
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