Villa Rosa

Villa Rosa is a splendid private estate nestled in the picturesque Tuscan countryside, just a short distance from the historic town of Cortona. This charming medieval gem traces its roots back to the ancient Etruscan civilization, which is still evident in the city today.

The property comprises a main villa and a separate elegant cottage. Together, they can comfortably accommodate up to 12 guests in six bedrooms, each with its own bathroom. These two delightful structures sit within close proximity, offering the perfect setting for group vacations while allowing for personal space and independence.

The estate is enveloped by meticulously manicured outdoor spaces adorned with an abundance of flowers and plants. A private pool basks in a sun-soaked position throughout the day. Sun loungers and umbrellas are thoughtfully provided for your relaxation under the Tuscan sun.

Villa Rosa boasts a stunning panoramic veranda complete with a dining table and outdoor sofas, perfect for savoring meals or sipping wine amidst the vibrant colors and scents of the countryside, set against a backdrop of breathtaking sunsets. Barbecue facilities are also available.

Perched in a lofty position and enveloped by woodlands, olive groves, and fragrant herbs, Villa Rosa offers an invigorating and rejuvenating atmosphere. Nature lovers can embark on scenic walks that lead to awe-inspiring vistas of the Tuscan countryside, neighboring Umbria, and Lake Trasimeno.

The villa and cottage have undergone extensive renovations, fusing the rich traditions of Tuscany with modern and stylish elements. The result is a unique property where every detail exudes character, luxurious comfort, and unparalleled beauty.

The villa, is spread across three levels, offering spacious rooms for group dining. The ground floor houses a fully equipped kitchen with a dining table and provides access to the living room, where a fireplace and satellite TV await. From the living room, you can step onto the rooftop terrace, perfect for al fresco dining. The ground floor also features two double bedrooms, each with direct garden access, and a bathroom with a shower. A beautiful stone staircase from the kitchen leads to a third double room with an en-suite shower.

The living room's staircase descends to the basement, where you'll find a study area/living room with another bathroom and shower, along with a second room fitted with a professional kitchen and dining table. This second kitchen offers direct access to the outdoors.

The cottage spans two levels, with the living area on the ground floor. Here, you'll find a fully equipped kitchen with a dining table and a sitting area complemented by a fireplace and satellite TV. French doors lead to a spacious sun terrace with outdoor furniture. The ground floor accommodates two bedrooms: a double room with an en-suite shower and a twin room, which can be converted into a double if needed, with an adjacent bathroom featuring a shower. A stone staircase from the living room leads to the third bedroom, a splendid suite with a private shower.

Bedrooms: 6 bedrooms

5 bedrooms with queen-size beds

1 bedroom with 2 twin beds

Capacity: 12 guests

Bathrooms: 6 full bathrooms

Décor: Antique elegant Tuscan

Amenities: Private garden and parking, fence around the entire property, gate, swimming pool with sun deck, sun beds, umbrellas, outdoor table and chairs, barbecue, washing machine, hair dryer, Wi-Fi, television, fully equipped kitchens, heating and air conditioning. *Heating and air conditioning incur an extra fee based on usage, to be paid at the end of your stay.

Location: in the valley below Cortona, about a 10-minute drive to town

The pool is open May 1st through October 15th


What your trip includes: 

  • Seven-night stay in the countryside about a 10-minute drive from the historic center of Cortona

  • Personalized planning assistance & local cortona concierge service who assist our guests in planning additional tours, experiences and other aspects of their stay 

  • Exclusive access to Stacey and Rob’s Insider Tips to Cortona


About our Insider Tips: Having lived in Cortona for over 20 years, Sojourn Ventures founders Stacey and Rob have created their highly acclaimed Insider Tips, an exclusive guide for our guests that provides tips about our favorite shops, restaurants, cafes, and other activities to experience in Cortona. Using this guide can give you a more personalized experience that goes above the standard tourist level, especially when you mention that you are “Friends of Stacey and Rob.” 

Additional Details:

  • Welcome packets will be emailed to winners upon notification of their purchase.

  • Reservations are based on availability. Stays are Saturday to Saturday only.

  • Package is valid for 2 years from the date of purchase. 

  • Airfare and ground transportation are not included. 

  • All sales are final. There are no cash refunds. Packages cannot be resold to a third party. 

  • Photos provided are actual images of the private homes pictured. In the rare event that a home is no longer available due to circumstances beyond our control, force majeure, property damage, and/or change of ownership, Sojourn Ventures reserves the right to provide a private home and experience of equal value and quality.

  • CANCELLATION POLICY: Cancellation prior to arrival may be subject to forfeiture of reservations and funds.

  • BLACKOUT DATES AND SURCHARGE RATES APPLY for the months of July and August as well as the weeks of Christmas, New Year’s, and Easter.