Book Luxury Airbnb Alternatives in Castiglion Fiorentino

We selected the 3036 homes worth renting in this location

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Home spotlights in Castiglion Fiorentino

Casa Castagna

Casa Castagna

  • 6 guests

  • 3 bedrooms

Castiglion Fiorentino, Arezzo

Nothing says ‘la dolce vita’ quite like this authentic Italian villa, which you’ll find tucked away on the outskirts of Castiglion Fiorentino. Nestled deep in the heart of the Tuscan countryside, this rustic home dates back to the 17th century, so it’s no wonder that stepping inside feels like travelling back in time.

The Lucia

The Lucia

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

This quintessentially Italian home is nestled in the countryside just 5 kilometres from the beautiful town of Cortona. Days here can be spent hiking, cycling and exploring the historic hilltop towns of Tuscany.

Between The Olive Groves

Between The Olive Groves

  • 24 guests

  • 12 bedrooms

Monte San Savino, Arezzo

When staying in Tuscany, who doesn’t want a 16th-century villa, with life-size frescoes and acres of grounds to explore? This place sits between the medieval borgo of Monte San Savino (a ten-minute drive) and the alluring city of Arezzo (a fifteen-minute drive).

By and By

By and By

  • 10 guests

  • 5 bedrooms

Fratticciola, Cortona

Ideal for a group of friends or perhaps a multi-generational break, this farmhouse is said to be the oldest building in the village and, although it's been smartly modernised, it's still beautifully traditional. Just as it would have been when it was built, the main house is divided into separate apartments – one upstairs and one on the ground floor.


We selected the top 3% holiday homes in Castiglion Fiorentino Airbnb Alternatives

Explore the 3036 most perfect homes in our collection

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Most popular homes in Castiglion Fiorentino

Tuscan Stone & Olive Trees

Tuscan Stone & Olive Trees

  • 2 guests

  • 1 bedrooms

Cortona, Arezzo

Tuscan Tradition

Tuscan Tradition

  • 8 guests

  • 4 bedrooms

Fratticciola, Cortona

Timeless Harmony

Timeless Harmony

  • 14 guests

  • 5 bedrooms

Arezzo, Tuscany

Limestone & Antique

Limestone & Antique

  • 12 guests

  • 6 bedrooms

Marciano della Chiana, Arezzo

Tuscan Garden

Tuscan Garden

  • 12 guests

  • 6 bedrooms

Castiglion Fiorentino, Arezzo

Upon a Golden Dream

Upon a Golden Dream

  • 8 guests

  • 4 bedrooms

Cortona, Arezzo

Noah's Son

Noah's Son

  • 2 guests

  • 1 bedrooms

Cortona, Arezzo

A Gift of Laurel

A Gift of Laurel

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

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Frequently asked questions

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