San Regolo, Vacation Villa in Tuscany, Italy

 

San Regolo is a spectacular luxury Tuscany villa rental offering 6,253 square feet of beautifully restored living space, breathtaking countryside views. Combining historic architecture with refined contemporary comforts, this exceptional six-bedroom retreat is ideal for families and groups seeking privacy, elegant surroundings, and an immersive Tuscan experience.

San Regolo offers guests the opportunity to experience one of Tuscany's most treasured countryside destinations. Originally established in the year 998, the estate evolved over centuries into a thriving agricultural community before undergoing an extraordinary restoration that carefully preserved its architectural heritage while introducing the luxuries expected by today's discerning travelers.

Surrounded by vineyards and native woodland, San Regolo has been thoughtfully restored to showcase the beauty of traditional Tuscan craftsmanship. Exposed timber beams, natural stone walls, elegant fireplaces, handcrafted details, and sophisticated Italian furnishings create interiors that are both warm and inviting. Expansive windows frame panoramic countryside views, while generous open-plan living spaces provide the perfect environment for gathering with family and friends after a day exploring the surrounding region. This is one of the estate’s largest homes, with a 3-bedroom main residence and two 1-bedroom guest houses — fitting for multi-family getaways or groups who enjoy their own space.

The outdoor spaces invite guests to embrace Tuscany's celebrated lifestyle. A stunning heated glass-tiled infinity pool overlooks the rolling hills, while beautifully landscaped gardens provide numerous places to relax beneath the Italian sun. Covered terraces, elegant outdoor lounges, and spacious alfresco dining areas create idyllic settings for leisurely breakfasts, afternoon aperitivos, and memorable dinners overlooking the countryside.

Guests staying at San Regolo enjoy access to an exceptional collection of estate amenities designed to celebrate the region's culture, cuisine, and natural beauty. Guests can explore scenic walking and cycling trails that wind through vineyards and olive groves savor exceptional Tuscan cuisine prepared with locally sourced ingredients, or discover the area's renowned wineries through guided vineyard tours and private tastings.

To further personalize your stay, a variety of exclusive in-house services can be arranged at an additional cost. Guests may enjoy private chef experiences private transportation, personal shopping, and customized celebrations for special occasions. For an especially memorable arrival, guests may also arrange a delightful four-course welcome dinner prepared by a talented local chef using fresh seasonal ingredients sourced from the surrounding countryside. Delivered upon arrival, this authentic Tuscan meal offers the perfect introduction to the region's renowned culinary traditions and can be added to new reservations when confirmed at least seven days before arrival.

Every reservation with Dream Exotic Rentals also includes our complimentary concierge service. With 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 exclusive winery visits, restaurant reservations, private cultural excursions, transportation, and bespoke itineraries tailored to your interests.

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