Castiglion Fiorentino vacation rentals
Vacation rentals in Castiglion Fiorentino by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.
Castiglion Fiorentino in Tuscany is surrounded by the scenic Val di Chio, with landmarks such as the Cassero Fortress, Pinacoteca Comunale, and the Church of Sant'Angelo al Cassero. Travelers visit for local wine tasting tours, participation in the Palio dei Rioni medieval festival, and enjoying the Tuscan countryside. On Houfy, book direct with local hosts in Castiglion Fiorentino. Discover rustic farmhouses, hillside villas, and quaint town apartments with easy access to nearby areas like Cortona and Arezzo. Olive harvest season in autumn offers a unique glimpse into traditional Tuscan agricultural life.
Recommended Homes in Castiglion Fiorentino
Handpicked properties we think you'll love in Castiglion Fiorentino.
€427.00 EUR total for 3 nights
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Villa mit privatem Pool in der Nähe von Cortona
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€999.00 EUR total for 3 nights
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Why visit Castiglion Fiorentino
Discover what makes Castiglion Fiorentino a perfect vacation rental destination.
Explore Etruscan Ruins
Ancient history comes alive.
Visit the Etruscan tombs dating back to the 6th century BC at the Cassero Archaeological Museum, just a 5-minute walk from the city center.
Tuscan Culinary Delights
Savor authentic Italian cuisine.
Enjoy local dishes like ribollita and pici pasta at Trattoria La Grotta, located in Piazza San Francesco, a mere 10-minute walk from your rental.
Scenic Val di Chiana
Beautiful landscapes for nature lovers.
Hike through the rolling hills and vineyards of the Val di Chiana countryside, which starts just 2 miles outside the town.
Annual Castiglion Film Festival
Celebrate cinema in the summer.
Join the community for screenings and workshops at the historic Teatro Comunale during this summer event, located centrally in town.
Where to stay in Castiglion Fiorentino
The best areas and neighborhoods for your vacation rental in Castiglion Fiorentino.
Centro Storico
This medieval heart of Castiglion Fiorentino offers cobbled streets and ancient architecture, perfect for history buffs.
Brolio
A quiet neighborhood surrounded by vineyards and olive groves, ideal for a peaceful retreat with scenic views.
La Nave
Known for its local markets and traditional Tuscan houses, providing a taste of authentic Italian living.
Montecchio Vesponi
Dominated by its medieval castle, this area offers stunning panoramic views of the surrounding valleys.
Castiglion Fiorentino vacation rentals with free WiFi, air conditioning or kids friendly
Free WiFi, air conditioning, kids friendly and more — every Castiglion Fiorentino vacation rental here is listed by a verified host and bookable direct, with the price the host set.
Top attractions in Castiglion Fiorentino
All within driving distance of Castiglion Fiorentino vacation rentals.
Cassero Archeological Museum
Featuring Etruscan artifacts and medieval finds. · 0.3 miles
Teatro Comunale
Hosts numerous cultural events and performances all year round. · 0.2 miles
Val di Chiana
A picturesque valley perfect for hiking and biking. · 2 miles
Loggia del Vasari
An architectural marvel offering panoramic views of the valley. · 0.1 miles
Trattoria La Grotta
A local favorite serving traditional Tuscan cuisine. · 0.5 miles
Pinacoteca Comunale
Displays Renaissance artworks and local artists. · 0.4 miles
Getting to and around Castiglion Fiorentino
Castiglion Fiorentino is accessible by train and car, with nearby airports offering regional connections.
- CASTIGLION FIORENTINO STATION
- Connects to major cities like Florence and Rome, with frequent daily services.
- A1 MOTORWAY
- Provides access via the Monte San Savino exit, 15 minutes away by car.
- PERUGIA SAN FRANCESCO D'ASSISI AIRPORT
- Located 47 miles away, offering flights to major Italian and European destinations.
Similar vacation rentals near Castiglion Fiorentino
Homes within 60 miles of Castiglion Fiorentino, from verified hosts.
€1,604.00 EUR total for 3 nights
Oct 7 – 10, 2026
![Villetta La Poderosa [Saturnia Hotsprings]](https://www.assets.houfy.com/assets/images/properties/332401/c818c0e5340be04d67bff39c3fbd6563.jpg?im_w=480)
![Villetta La Poderosa [Saturnia Hotsprings]](https://www.assets.houfy.com/assets/images/properties/332401/f8e82171432ea6c1ab3abdc9c1d649ae.jpg?im_w=480)
![Villetta La Poderosa [Saturnia Hotsprings]](https://www.assets.houfy.com/assets/images/properties/332401/9642a01fb6df6335689a4521dc1fe943.jpg?im_w=480)
![Villetta La Poderosa [Saturnia Hotsprings]](https://www.assets.houfy.com/assets/images/properties/332401/0499d8d73ec2756035fb97138059512c.jpg?im_w=480)
![Villetta La Poderosa [Saturnia Hotsprings]](https://www.assets.houfy.com/assets/images/properties/332401/60ec106ed2d8d6bc428db79190ab40f2.jpg?im_w=480)
€646.75 EUR total for 5 nights
Oct 13 – 18, 2026
€360.00 EUR €306.00 EUR total for 3 nights
Sep 29 – Oct 2, 2026
€12,647.34 EUR total for 6 nights
Jun 20 – 26, 2027
€240.00 EUR total for 3 nights
Sep 28 – Oct 1, 2026
€5,600.00 EUR total for 7 nights
Oct 24 – 31, 2026
$432.00 USD total for 3 nights
Sep 26 – 29, 2026
€258.00 EUR total for 3 nights
Sep 26 – 29, 2026
Explore near Castiglion Fiorentino
Cities and towns within driving distance of Castiglion Fiorentino, each bookable direct with the host.
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More vacation rental destinations around Castiglion Fiorentino
Frequently asked questions
Quick answers about booking vacation rentals in Castiglion Fiorentino and what direct booking on Houfy actually means.
The average price for vacation rentals ranges from €70 to €150 per night, depending on location and amenities.
Yes, many rentals in Castiglion Fiorentino welcome pets. Look for listings that specify pet-friendly policies.
Centro Storico is popular for its historic charm, while Brolio is perfect for nature lovers.
Visit in late spring or early autumn for pleasant weather and fewer tourists.
Choices range from rustic farmhouses to modern apartments, with options for all group sizes.
Rentals offer more space and privacy, often at more competitive prices than hotels.
Don't miss the Palio dei Rioni, a medieval horse race festival held every June.
Houfy is a platform for booking vacation rentals; guests pay the listed price directly to the host.
Yes, Houfy provides secure, direct transactions with verified hosts, ensuring a safe booking experience.