Villa Simonetta

Villa Simonetta comprises two distinct structures: the primary villa, subdivided into two separate apartments, each with its own private entrance and garden. Both apartments are elegantly furnished in the classic Tuscan style, showcasing meticulous attention to detail and comfort.

Additionally, situated in front of the main villa is a charming cottage, housing the third apartment. This unit is also tastefully adorned with typical Tuscan decor and boasts a private entrance and garden.

The larger of the two apartments within the main villa, with its entrance on the ground floor, can comfortably accommodate up to 6 individuals. It spans two floors, featuring a living area on the ground floor and sleeping quarters on the first floor, connected by a stone staircase.

The second apartment, also accessible from the ground floor, offers accommodation for up to 4 people. This unit is spread over two levels, with the living area on the ground floor and the sleeping area on the first floor, connected by an internal wooden staircase.

The cottage, situated just a few steps away from the primary building, can host up to 4 guests. It, too, is distributed over two stories, with the living area and one bedroom on the ground floor, and the second bedroom on the first floor, connected by an internal wooden staircase.

Bedrooms: 7 bedrooms with queen-size beds

Capacity: 14 guests

Bathrooms: 5 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 from April 15th 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.