Book Luxury Airbnb Alternatives in Gaiole in Chianti

We selected the 2704 homes worth renting in this location

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Home spotlights in Gaiole in Chianti

Vineyard Sunset

Vineyard Sunset

  • 6 guests

  • 3 bedrooms

Radda in Chianti, Tuscany

Nestled in the Tuscan countryside with a private pool, serene outdoor space and views across Chianti’s vineyard-laced hills – what’s not to love about this home? Comfortable for a family or group of friends, inside, you’ll find a seamless blend of traditional and modern.

Chianti Lake

Chianti Lake

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

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 sunbathe.

Oak & Vine

Oak & Vine

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

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 quality time with your loved one, whether sunbathing, dining alfresco or raising a glass in a toast to your holiday.

The Olive Vine

The Olive Vine

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

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 living space, which opens out onto several terraces and a leafy garden with an infinity pool.


We selected the top 3% holiday homes in Gaiole in Chianti Airbnb Alternatives

Explore the 2704 most perfect homes in our collection

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Most popular homes in Gaiole in Chianti

Hillside Harvest

Hillside Harvest

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

My Chianti Heart

My Chianti Heart

  • 12 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

Tuscan Bloom

Tuscan Bloom

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

Mulberry & Olive

Mulberry & Olive

  • 6 guests

  • 3 bedrooms

Casanuova di Ama, Gaiole in Chianti

The Olive Dawn

The Olive Dawn

  • 4 guests

  • 2 bedrooms

Gaiole in Chianti, Siena

The Rosso

The Rosso

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Chianti Dream

Chianti Dream

  • 4 guests

  • 2 bedrooms

San Sano, Gaiole in Chianti

Whispering Cypresses

Whispering Cypresses

  • 6 guests

  • 3 bedrooms

Montevarchi, Arezzo

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Frequently asked questions

Airbnb is a shot in the dark. We meticulously vet all our homes in Gaiole in Chianti to ensure you won’t waste your precious holiday. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury Gaiole in Chianti Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.

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