Discover Tuscany and Umbria with us.

Vacation rentals, tours and experiences in the heart of Italy

On vacation, your only worry should be what to order at a restaurant. For a truly stress-free holiday, allow us to take care of any arrangements you may need during your stay.

The comfort of a private home

From cozy to spacious, luxury to rustic charm, our portfolio comprises of over 60 properties in some of central Italy's most enchanting landscapes. We have options for all ages and groups of all sizes, as well as for different budgets. The one thing they all have in common is the great service the guests receive.

Book your vacation rental online

Select your preferred dates below and then click the submit button to check availability and pricing.

Experiences worth writing home about

It’s hard to find other areas with so many UNESCO world heritage sites, works of art, monuments and picturesque villages. Wherever you look you’ll find beauty, from the incredible churches and castles, to the serene splendor of the hilly countryside.

Wholesome food and sublime wine

From classes in wineries and countryside villas to lessons held right in the comfort of your own accommodation, we offer plenty of occasions to gather around a table with your favorite people and enjoy life's simple joys.



Casa Sogni

Tranquil and airy, this independent house is located in a small hamlet just outside the walls of Cortona. A former convent, it still maintains some of the original sandstone.
Tuscany vespa tour

Vespa tour

Discover the treasures that await beyond the usual routes on this tour. You’ll be joined by a guide and you’ll get to know (and taste!) some of the area’s most famous exports.
cooking class

Private Chefs and Catering

Enjoy delicious catered meals in the comfort of your vacation rental, whether it is for one day or the entire duration of your stay.

What our guests say

Honest feedback from travellers who booked with us.

Denyse & her staff were fantastic in helping to plan our vacation to Tuscany.

Anne Elam

I would recommend Together in Tuscany & Umbria to all my friends traveling to Italy.

Tom and Sherry Reis

My guests and I enjoyed a trip of a lifetime thanks to Denyse, her guides and drivers! 

Bonnie Wong

How to find us

Our offices are a 2-min walk from the Terontola-Cortona train station and within easy reach of the highway. On-street parking is available immediately outside.

Together in Tuscany & Umbria

via XX settembre, 26
52044 Cortona, Italy
> Click here for GPS coordinates