Book Luxury Vacation Rentals in Castiglion Fiorentino

A Tuscan Sunrise

• 6 guests

• 3 bedrooms

Montecchio, Castiglion Fiorentino

Tucked between olive groves and a pine forest, this cosy villa is a scenic drive away from Cortona, Arezzo and Pienza – but you might not want to leave once you're here. The three bedrooms (each with their own bathroom) are downstairs, while upstairs it’s all about spending time together – cooking in the kitchen, chatting around the travertine island, or sharing a bottle of local wine at the glass-and-timber table made from a tree that once grew on the property.

Wild Rosemary

• 10 guests

• 5 bedrooms

Castiglion Fiorentino, Arezzo

A truly idyllic escape to rural Tuscany requires rolling hills, a rustic farmhouse and panoramic views across olive groves and vineyards. And you'll have all of this and more at this beautiful home deep in the countryside between Arezzo and Cortona.

Sunflower Beams

• 3 guests

• 2 bedrooms

Cortona, Arezzo

Located in Cortona’s historic centre, this handsome apartment blends rustic charm with modern comforts to create a memorable, relaxing stay. Housed in a historic building, you’ll find plenty of traditional features here including exposed dark wood beams and terracotta floor tiles sitting alongside inviting contemporary furnishings to create the perfect mix of old meets new.