Book Luxury Airbnb Alternatives in Castellina in Chianti

We selected the 2714 homes worth renting in this location

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Home spotlights in Castellina in Chianti

The Olive Tint

The Olive Tint

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

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 great fit for families with a lovely private garden as well as flexible sleeping arrangements – the twin beds can be converted into doubles upon request.

Dreaming of Chianti

Dreaming of Chianti

  • 6 guests

  • 3 bedrooms

Castellina in Chianti, Tuscany

After a day touring world-class vineyards, this home is the perfect place to unwind with a glass of Chianti. Sure, there’s no air conditioning here, and the traditional interiors may not be to everyone’s taste, but there’s no denying the beauty of the outdoor space.

Over the Chianti Hills

Over the Chianti Hills

  • 4 guests

  • 1 bedrooms

Barberino Tavarnelle, Florence

Over the Chianti Hills and far away lies an abundance of Tuscan charm and Mediterranean serenity. Set in the ancient medieval village of San Donato, you'll get a quintessential Italian countryside experience with captivating views over the Tuscan landscape to remind you of your dreamlike location at every opportunity.

The Tuscan Muse

The Tuscan Muse

  • 14 guests

  • 7 bedrooms

Tregole, Tuscany

With majestic views across rolling hills and olive groves, this home makes it easy to enjoy the magic of Italy. Set within a working winery, you’ll be treated to an authentic taste of rural life along with all the essentials you could need to slow down and spend quality time together.


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

Explore the 2714 most perfect homes in our collection

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Most popular homes in Castellina in Chianti

The Rosso

The Rosso

  • 8 guests

  • 4 bedrooms

Radda in Chianti, Tuscany

Vineyard Sunset

Vineyard Sunset

  • 6 guests

  • 3 bedrooms

Radda in Chianti, Tuscany

Chianti Rosemary

Chianti Rosemary

  • 4 guests

  • 2 bedrooms

Castellina in Chianti, Tuscany

The Papessa

The Papessa

  • 6 guests

  • 2 bedrooms

Barberino Tavarnelle, Florence

The Olive Stone

The Olive Stone

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

Wild Roses

Wild Roses

  • 10 guests

  • 5 bedrooms

Radda in Chianti, Tuscany

A Little Bit of Chianti

A Little Bit of Chianti

  • 4 guests

  • 2 bedrooms

Castellina in Chianti, Tuscany

Sunflowers & Sangiovese

Sunflowers & Sangiovese

  • 10 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

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Frequently asked questions

Airbnb is a shot in the dark. We meticulously vet all our homes in Castellina 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 Castellina 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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