Cortona Vacation Rentals

TuscanDream represents only the finest villas in Cortona Italy, many of them air-conditioned and all available with a full staff to make sure that your holiday is a celebration of happiness and contentment!

Cortona is a majestic medieval city in the province of Arezzo rising above the lush and fertile Val di Chiana. The town was made famous by the classic romantic comedy, Under the Tuscan Sun, which was filmed at Villa Laura, one of the sensational villas in Cortona which TuscanDream is proud to represent!

We have personally visited all our villas in Cortona Italy and we know the owners, the neighborhood, and all the details you want to know.

Experience Cortona Luxury – from Food to Scenery

Guests lucky enough to rent a villa in Cortona through TuscanDream quickly fall in love with the breathtaking scenery and the famed Cortona cuisine and hospitality!

Cortona is famous for its Syrah grapes and produces fabulous wines including Baracchi Smeriglio Ardito. When you rent a villa in Cortona through TuscanDream you not only are getting a spectacular villa, but you are getting a dedicated team of professionals who will be able to assist you with every facet of your holiday.

We know the pulse of Cortona and can guide you to the best restaurants and take you on fabulous wine tours. Our experienced guides can take you to the splendid Piazza della Repubblica and Piazza Signorelli highlighting the history and celebrating the artistic masterpieces at the city center.

Cortona is one of the most glorious cities in all of Italy and TuscanDream invites you to come join us under the Tuscan sun and celebrate the joy that is Tuscany by spending your next vacation in Italy in a Cortona Villa!

Villa Laura Cortona Under the Tuscan Sun Villa

Under the Tuscan Sun Villa in Cortona – Villa Laura

Cortona | 9 Bedrooms | 13 Bathrooms Air Conditioned, Staffed Villa, Wi-Fi

Book now

Villa Santa Croce – Historic 12th Century Rental Villa in Cortona

Cortona | 7 Bedrooms | 7 Bathrooms Bocce Court, Ancient Olive Grove

Book now

Hero

Not Sure Which Villa to Choose? We’re Here to Help.

Speak to a villa specialist

Local experts,
Internationally operated

Run entirely by an Italian team with deep local expertise and the efficiency and responsiveness international clients expect.

Over 20 years of experience

With over two decades of experience, we know how to design holidays filled with unforgettable moments, cultural richness, and seamless logistics.

Personalized travel planning

We have an expert English-speaking concierge team—all locals from the region—we can craft the holiday that's perfect for you.

Most exclusive villas in Tuscany

Thanks to decades-long relationships with villa owners, we offer access to the most exceptional and exclusive properties in Tuscany.