Book Luxury Airbnb Alternatives in Castellina in Chianti

We selected the 3876 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.

First Of The Summer Wine

First Of The Summer Wine

  • 6 guests

  • 4 bedrooms

Castellina in Chianti, Tuscany

Surrounded by olive trees and vast swathes of vineyards, this Tuscan home in the heart of the Chianti wine region is a haven of rural relaxation. Its exposed stone exterior gives way to a bright interior, where farmhouse simplicity meets elegant design in the living room.

Paolo's Vine

Paolo's Vine

  • 6 guests

  • 3 bedrooms

Galenda, Gaiole in Chianti

This beautiful home is a secluded base in Chianti. It’s surrounded by the hills and vineyards of the countryside and boasts 180-degree views.

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.


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

Explore the 3876 most perfect homes in our collection

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Most popular homes in Castellina in Chianti

Sun of Splendour

Sun of Splendour

  • 15 guests

  • 7 bedrooms

Fonterutoli, Castellina in Chianti

A Taste of the Hills

A Taste of the Hills

  • 2 guests

  • 1 bedrooms

Castellina in Chianti, Tuscany

The Summer Harvest

The Summer Harvest

  • 14 guests

  • 7 bedrooms

Castelnuovo Berardenga, Siena

Stonehill Vines

Stonehill Vines

  • 6 guests

  • 3 bedrooms

Radda in Chianti, Tuscany

The Etruscan View

The Etruscan View

  • 4 guests

  • 2 bedrooms

Galenda, Gaiole in Chianti

The Tuscan Muse

The Tuscan Muse

  • 14 guests

  • 7 bedrooms

Tregole, Tuscany

Being of Beauty

Being of Beauty

  • 18 guests

  • 9 bedrooms

Lilliano, Castellina in Chianti

Chianti Classico

Chianti Classico

  • 12 guests

  • 6 bedrooms

Radda in Chianti, Tuscany

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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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