San Damiano, Vacation Villa in Tuscany, Italy

San Damiano is a beautifully restored luxury Tuscany villa rental offering 4,736 square feet of elegant living. Set within an extraordinary private estate whose history stretches back to the year 998, San Damiano offers guests the rare opportunity to experience more than a millennium of Tuscan heritage.

San Damiano enjoys one of the estate's most tranquil and picturesque settings. Originally inspired by the classic Tuscan farmhouse, the residence has been thoughtfully reimagined with refined interiors that celebrate both tradition and contemporary design. Designed to accommodate up to eight guests, the property features a spacious three-bedroom main residence complemented by a private one-bedroom guest house, providing the ideal balance between shared gathering spaces and personal privacy. The open-plan living areas include two comfortable lounges, one centered around a traditional fireplace, an elegant dining room with panoramic countryside views, and a fully equipped gourmet kitchen with breakfast bar that opens onto the outdoor pergola.

San Damiano features heated glass-tiled infinity pool, overlooking the sweeping valley below, while a relaxing hot tub positioned beside the pool offers the perfect place to unwind. Multiple outdoor dining and lounge areas encourage leisurely afternoons and unforgettable evenings beneath the stars, complemented by a traditional wood-fired forno, barbecue, and a striking stone-built fire pit where family and friends can gather to share exceptional local cuisine and fine regional wines. Private hiking and cycling trails begin just beyond the villa, inviting guests to immerse themselves in the estate's peaceful forests and natural surroundings.

To further enhance your stay, a wide range of personalized in-house services can be arranged at an additional cost. Every reservation with Dream Exotic Rentals also includes our complimentary concierge service. Backed by more than 25 years of experience creating exceptional luxury vacations around the world, our dedicated concierge team is available before and throughout your stay to arrange winery visits, private cultural excursions, restaurant reservations, transportation, and fully customized itineraries. From your arrival to your departure, every detail is thoughtfully planned, ensuring your stay at San Damiano is seamless, authentic, and truly unforgettable.

Check-in: 4:00 – 5:00 PM

Check-out: 10:00 AM

Ask about late or early check-in/out

Children welcomed (ask about age restrictions when applicable)

Events (inquire)

Pets (inquire)

No Smoking (penalty for smoking, damages applicable)

Rates vary depending on time of year

High season and holiday rates are higher

4 to 7 night minimum (based on season and arrival date)

Taxes shall apply to final bill

Refundable damage deposit to vary by capacity/length of stay

50% required to book your dates (ask if you need an exception)

Balance due 60 days prior to arrival (ask if you need more time)

Bring identification for verification upon check-in

Ask about trip cancellation & medical trip insurance

Please follow guidelines for travel, ask your travel advisor for updates

Concierge is included for planning & booking excursions

Unless otherwise noted, ask about cancellation policies which change rapidly

Bring a mask for your own protection in case of mandate