Villa del ColleN°001
Umbria, Italy
Torgiano
Oct 21 – 26 · $9,544 for 5 nights
Smiling House brings together 3 hand-selected luxury villas in Umbria — each one chosen for its setting, its design and the service around it. Umbria, the green heart of Italy, is a landlocked region of medieval hill towns, vineyards and woodland. From intimate hideaways for two to expansive homes for family and friends, every villa is booked directly with our team — no middle-man, no surprises. Browse the homes below, then speak to a concierge who knows Umbria first-hand about dates, rates and the details that make a stay effortless.
Updated October 2026
Torre Del Melograno With Heated PoolN°002
Umbria, Italy
Castiglione in Teverina
From $493 per night
Villa San MartinoN°003
Umbria, Italy
Torgiano
Oct 20 – 24 · $4,307 for 4 nights
All 40 villas in Umbria
Every home in Umbria that can be booked with Smiling House, as a plain list.
- 19th Century Villa near Medieval Small Villages
- Adorable Posh Villa Overlooking Umbrian Hills
- Beautiful Private Hamlet With Pool and Views
- Beautiful Villa With An Oasis Of Peace All Around
- Best Escape Villa Surrounded by Meadows and Trees
- Private Pool Villa in Città della Pieve
- Casale Montemoro – Private Pool & Garden | Sleeps 10
- Cozy Two-Bedroom Retreat in Città Della Pieve
- Charming Medieval Villa Overlooking Assisi City
- Classic Middle Age Castle
- Exclusive Villa in San Giustino with Swimming Pool
- Fontesecca
- Fresh Oasis Villa with Private Deluxe Pool
- Girasole Apartment with Shared Pool 9 pax
- Glamorous Stone Villa With Insane View & Pool
- Historic Farmhouse Villa With Beautiful Mini jacuzzi
- Historic Villa in a Beautiful Area
- Il Giuncheto, Pool, Amazing View, Umbrian Countryside - Il Giuncheto Casale
- Il Giuncheto, Pool, Amazing View, Umbrian Countryside - Il Giuncheto Lago
- Majestic Paradise Villa Facing Green Sea of Umbria
- Opulent Estate with Views of the Entire Valley
- Poggio Padule
- Rustic Luxury – A Timeless Countryside Retreat
- Scenic Authentic Countryside Villa
- Scenic Landscape Villa in Umbria
- Serene Villa Surrounded by Fruit Trees and Forest
- Suite Sinfonia Blu
- Suite Sinfonia Oro
- Sweet Romance Villa with Beautiful Sunset Views
- Torre Del Melograno With Heated Pool
- Truly Enchanting Villa Near from Amelia
- Typical Farm Villa near Orvieto and Lake Trasimeno
- Ultimate Luxury Villa With Private Pool
- Umbria's Prime Estate near Citta di Castello
- Umbrian Charm With Poolside Relaxation
- Umbrian Paradise With Private Pool
- Charming Villa with Large Pool in Umbria
- Villa San Martino
- Villa With Timeless Elegance And Tranquility
- Villa del Colle
Smiling House also offers a concierge for private chefs, transfers, ski instructors, yachts and cars, a VIP Club with first access to new residences and member rates, chalets for sale in the Gstaad region through its real estate division and instantly bookable homes with live availability.
More to rent in Umbria
Villas in other destinations
Frequently asked
How do I book a villa in Umbria?
Choose a home below and send an enquiry, or ask to book directly. A Smiling House concierge confirms availability and rates with the owner and handles the booking end to end — you deal with our team, not a faceless platform.
What's included when I rent a villa in Umbria?
Every home is fully furnished and privately yours for the stay. Concierge support, and often housekeeping and local recommendations, come as standard; specific services vary by property and are listed on each home's page.
Is it cheaper to book direct with Smiling House?
Booking direct removes the platform mark-ups that sit on OTA listings, and puts you in touch with a team that knows Umbria personally. You get the real home, the real price and a human who answers.
How many villas are available in Umbria?
3 villas are featured here right now. Inventory changes as homes are booked and new ones join, so the collection is always current.