Villa Sebastiano

Join us in Cortona, one of Tuscany’s ancient Etruscan hill towns, with its picturesque medieval buildings and spectacular vistas of the Val di Chiana and beyond. Cortona is perfectly situated to explore all the rich culture that Tuscany has to offer: gastronomical delights, world-class wines, Renaissance art, historic architecture, the generosity of the Italian spirit and so much more. Come create treasured Tuscan memories that will last a lifetime!

Nestled in the scenic countryside just below the historic town center, Villa Sebastiano is a spacious villa with panoramic views of the Tuscan hillside. The home features sprawling manicured gardens and lovely space for dining al fresco. The villa itself is divided into two separate apartments that feature their own kitchenette while still having a large main kitchen for cooking and gathering. Throughout the gardens, there are furnished patios where for relaxation, dining, and sunbathing. Sun loungers and umbrellas also line the private swimming pool. The villa has private parking on-site.

Bedrooms: 7 bedrooms with queen-size beds and twin-size beds

Capacity: 14 guests

Bathrooms: 5 full bathrooms

Décor: Traditional Tuscan

Amenities: Air conditioning, television, Wi-Fi, dishwasher, oven, stove, fridge and freezer, coffee maker, toaster, kettle, washing machine, iron and ironing board, hairdryer, barbecue, swimming pool, parking on-site. *Heating and air conditioning incur an extra fee based on usage, which is to be paid at the end of your stay.

Location: Tuscan countryside just below Cortona

The pool is open April 30th through September 30th


What your trip includes: 

  • Seven-night stay in the countryside, a 5-10 minute drive to 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.