Villa Carlotta

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!

The gorgeous and quintessentially Tuscan Villa Carlotta is nestled between rows of cypress trees on the bucolic rolling slopes of the countryside below Cortona. Although the home is just a short drive from the historic center, its location offers a great sense of privacy and exclusivity, complete with breathtaking views of the vineyards and olive groves in the surrounding valley and the city of Cortona on the mountain above.

Villa Carlotta's incomparable vistas can be best enjoyed while taking a refreshing swim in the home's elegant infinity pool. This crystal blue pool is surrounded by a pristine green lawn as well as complete outdoor lounging and dining areas with a full barbecue, perfect for grilling up Tuscan ingredients from the local market. 

The interior of this recently renovated villa features beautiful traditional Tuscan adornments as well as modern amenities throughout, offering maximum comfort and style. With thick stone walls, wooden-beamed ceilings below terra cotta roofing, and arched glass doorways opening up to the garden and landscape beyond, Villa Carlotta makes you feel at every turn that you are anchored in the Tuscan soil.

Property type: Countryside Villa

Bedrooms: 3 bedrooms with queen-size beds

Bathrooms: 3 full bathrooms: 1 full en-suite bath, 2 full bathrooms

Extra Sleeping: 1 double sofa bed in ground floor smaller living room

Capacity: 8 guests

Décor: Elegant traditional/modern Tuscan

Amenities: Garden, swimming pool, full kitchen, Wi-Fi, hair dryer, washing machine, enclosed property, safety gate surrounding pool, outdoor chaise longues, television, fireplace, barbeque, outdoor kitchen, on-site parking, heating and air conditioning in the 2 upstairs bedrooms. *Heating and air conditioning incur an extra fee based on usage, to be paid at the end of your stay.

Location: Foothills (Il Castagno) directly below Cortona, a 10 to 15-minute drive from central Cortona.

Check-in/check-out: Saturday to Saturday stays only.

The pool is open from April 15th - October 30th


What your trip includes: 

  • Seven-night stay in the Tuscan countryside, about a 10-15 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.