Tuscan Shadows
10 guests
5 bedrooms
Castiglion Fiorentino, Arezzo
Set high in the Tuscan hills, this villa has everything you need for a carefree stay. With a private pool and two terraces, you'll probably spend most of your time in the garden.
Luxury Long Stay Rentals in Castiglion Fiorentino
We selected the 2834 homes worth renting in this location
Home spotlights in Castiglion Fiorentino
Citrus & Sangiovese
10 guests
5 bedrooms
Cortona, Arezzo
Tucked away in the Tuscan countryside, this home offers a taste of rural Italian life. You’re quite secluded here – the nearest supermarket is a short drive away – but the views over the Val di Chiana are well worth the price of admission.
Rosewood Manor
18 guests
9 bedrooms
Castiglion Fiorentino, Arezzo
This Tuscan villa was once a hotel, so it’s well set up for large groups. All of the bedrooms are en-suite, there’s an industrial kitchen, and the huge lounge has plenty of sofas.
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 Long Stay Rentals
Explore the 2834 most perfect homes in our collection
View on map
Check upcoming rates & availability for Castiglion Fiorentino Long Stay Rentals
Frequently asked questions
Similar destinations
Explore our collection of luxury Extended Stay Rentals available for you to rent in Castiglion Fiorentino, Arezzo, Tuscany, Italy. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Castiglion Fiorentino, Arezzo, Tuscany, Italy collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.
Search our collection