Holiday Rentals in Umbria

Discover our handpicked holiday rentals in Umbria and on the Tuscany border. Every property is personally managed and inspected by Tony, so you can book with confidence, knowing each villa is maintained to a high standard. To learn more or book your stay, use the links below each villa image.
Time to Relax at one of these luxury villas in Umbria
Villa Tegolaio – A premier luxury estate that Tony has personally managed for more than two decades. This extraordinary length of service reflects the absolute trust, consistency, and meticulous attention to detail required to maintain a high-end rental property at its peak value year after year.
Location: Tuscany / Umbria Border
Capacity: Sleeps 10 | 4 Bedrooms | 4 Bathrooms
Originally a traditional tobacco barn, Villa Tegolaio has been beautifully converted and fully renovated to a premium standard, blending modern comforts with original features.
- The Space: Offers four large bedrooms, a well-appointed open kitchen, and a dedicated study containing a double sofa bed and television.
- Family & Group Friendly: The villa features a fully fenced, secure garden and a children’s play area, making it perfect for those travelling with small children.
- Outdoor Living: Unwind in landscaped gardens or float in the large, private fenced swimming pool offering incredible panoramic views across the valley.




👉View & Book Villa Tegolaio here
Casa Isabella – A stunning property under Tony’s dedicated oversight for the last four years. We handle the complete coordination of trusted specialists, ensuring the villa is perfectly prepared, flawlessly presented, and structurally immaculate for the owner’s peace of mind.
Location: San Leo Bastia
Capacity: Sleeps 6 | 3 Bedrooms (5 Beds) | 1 Bathroom
Perched on a picturesque hilltop between Cortona and Città di Castello, Casa Isabella is nestled within 20,000 m² of serene forests and meadows, offering the perfect countryside escape.
- Relaxation & Wellness: Features its own private sauna and a private swimming pool with spacious terraces perfect for sunbathing.
- Scenic Surroundings: Enjoy peaceful walks or bike rides through nature, accompanied at all times by stunning panoramic views.
- Outdoor Comfort: Multiple cozy seating areas are scattered around the grounds, ideal for relaxing and unwinding in absolute tranquility.




👉 View & Book Casa Isabella here
Looking for Another Villa?
The villas featured on our website are personally managed and inspected by Tony, ensuring they meet the high standards our guests expect.
Tony also manages several other holiday properties in Umbria that are not currently featured on our website. If you’re looking for a larger villa, different location, or have specific requirements, please get in touch. We’ll be happy to discuss your needs and, where possible, recommend a suitable property from our trusted network.
Contact us today and let us help you find the perfect holiday villa in Umbria or on the Tuscany border.
