Book Luxury Airbnb Alternatives in Siena

We selected the 3256 homes worth renting in this location

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Home spotlights in Siena

A Rustic Reverie

A Rustic Reverie

  • 4 guests

  • 2 bedrooms

Sovicille, Tuscany

For a taste of authentic Tuscan living, this holiday home is a great choice. This apartment is one of six, renovated from a 15th-century structure by a historically conscious architect.

Rolling In Olives

Rolling In Olives

  • 14 guests

  • 7 bedrooms

Stellino, Castelnuovo Berardenga

This traditional farmhouse, buried deep in the Tuscan hills, offers guests a taste of everything this area is known for – picturesque mountain views, pretty vineyards and lush olive groves. Sat in the heart of 'Chiantishire', you’re surrounded by idyllic villages like Castellina and Radda, and perfectly placed to explore this world-renowned wine region.

Toscana Per Sempre

Toscana Per Sempre

  • 2 guests

  • 1 bedrooms

Gaiole in Chianti, Siena

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 in the shared grounds, while the private terrace with its countryside views is perfect for a celebratory sundowner after a day of fun and exploring.

Tuscan Delight

Tuscan Delight

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Nestled on a hillside in Chianti with far-reaching views, this ground-floor apartment is part of a small resort. While it does lack natural light in some areas due to its history as a farm building, it’s comfortable and well-equipped for a restful retreat.


We selected the top 3% holiday homes in Siena Airbnb Alternatives

Explore the 3256 most perfect homes in our collection

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Most popular homes in Siena

Land of Beauty

Land of Beauty

  • 12 guests

  • 6 bedrooms

Castelnuovo Berardenga, Siena

The Olive Stone

The Olive Stone

  • 6 guests

  • 3 bedrooms

Gaiole in Chianti, Siena

Tranquil in Tuscany

Tranquil in Tuscany

  • 5 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Tuscan Hills

Tuscan Hills

  • 4 guests

  • 2 bedrooms

Monte Sante Marie, Asciano

Dreaming of Chianti

Dreaming of Chianti

  • 6 guests

  • 3 bedrooms

Castellina in Chianti, Tuscany

My Chianti Heart

My Chianti Heart

  • 12 guests

  • 4 bedrooms

Gaiole in Chianti, Siena

Chianti Sunrise

Chianti Sunrise

  • 4 guests

  • 2 bedrooms

Castelnuovo Berardenga, Siena

Chianti Views

Chianti Views

  • 6 guests

  • 3 bedrooms

Castelnuovo Berardenga, Siena

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Frequently asked questions

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