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Hugo II

Tuscany: Cortona
Reference number: U3
Sleeps: 10
Bedrooms: 5
Bathrooms: 5
Square feet: 2800

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Hugo 2 is a charming ivy-covered stone house located in a peaceful position below the town of Cortona.

This Cortona villa rental is situated on the grounds of a large and beautiful estate owned by the same family for almost 200 hundred years. The interiors are very comfortable and elegant, with some very nice antique furniture and botanical prints, the color palette is soothing mix of soft yellow, sage green and light blue.

Just outside the entrance is a paved terrace looking out on the valley below, comfortable outdoor couches  and dining table. The pool is located behind the owner’s villa, and access is via a private tree lined pathway. The gardens that surround the estate are quite lovely and perfectly maintained by the staff.


Contact us for Availability

For those guests who enjoy walking, Cortona can be reached in approximately 40 minutes ( uphill) along a former Roman road.

Prices 2024

(price per week in U.S dollars)



  • Final cleaning
  • Washing machine
  • Wireless internet
  • Dishwasher
  • BBq
  • A/C


  • Phone : Based on usage
  • Heating : Based on usage
  • Air Conditioning Extra based on usage
  • Final Cleaning Euro 250


First Floor

A large living/dining room with fireplace, bedroom with double bed and private bathroom. A Galley-style kitchen with beautiful olive wood counters. Stairway to the second floor

Second Floor

Two large air-conditioned bedrooms (one with queen size bed, one with two single beds), two bathrooms with shower, one of which is an en-suite to the twin bedroom, screens on bedroom and bathroom windows

two bedroom suite

Access via an exterior staircase

Living room with fireplace, dining room, kitchen, two king-size bedrooms with en-suite baths

Arrivals and Departures

Friday Arrival: from 4 pm to 6 pm/Departure no later than 9:30 AM

Security Deposit

400.00 In Euro. To be paid upon check in

Pool dates

May 10th – September 30th

Depending on weather

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Exceeded expectations for a villa stay in Italy!

Exceeded expectations for a villa stay in Italy!

We cannot say enough about how wonderful our stay at Hugo II was this July! Writing this in August and the memories are still making me smile. Hugo and his family are perfect hosts; there if you need them, but don’t intrude on your vacation. Their property is amazing from the gigantic pool and postcard worthy grounds to the charming outdoor and interior spaces. We spent the bulk of our time outside or at the pool. The interiors are a little dark, but probably by design to keep it cool, and with the stunning landscapes outside your door, you won’t spend much time inside. The beds and bedding were over the top awesome. Bring bug spray and pick up some citronella candles at the store if you are going in the summer. Mosquitos are not horrible compared to other places we’ve been, but they are there.

Ideal for two families of 4+ who want separate separate spaces. We loved the grocery store at the bottom of the hill, but really relished eating out at all the great restaurants Cortona had to offer. Great food is remarkably reasonably priced and we loved experiencing local cuisine. We walked to Cortona on the old trail, but it was blazing hot, so drove in a lot as well. You could spend at least several days just exploring around Cortona, but it was also a great jumping off spot to explore other hill towns and the Val d’Orcia.

John and Michelle at Italian Town and Country were invaluable to us in planning our trip. They matched us with just the right place and went the extra mile. Hands down the best way to rent a villa and have the confidence that your experience will be unforgettable and free of unpleasant surprises. Would go back and do it all again in a heartbeat!

Heather & Sam Berger

Paradise at Hugo2

We were in Paradise at Hugo2 villa. The setting, the pool, eating all our meals outside, the hike to Cortona, the great little market at the bottom of the hill–all of it was the highlight of our trip to Italy.

The owner is also was a godsend, as we needed to arrange some transportation for a few of our party and there was a train strike in Italy. He arranged a very reasonable cab driver to pick up a few of them from Florence at midnight and drive them to the villa. Wow, what a relief.

We were just so happy with everything–including Ada and Enzo.
Thank you, thank you!
Jeanie, Tom and family

Hugo 2

Hi John,
It was absolutely amazing! We loved Cortona so much. I would go back in a heartbeat. Hugo2 was beautiful. The grounds were spectacular, as was the huge pool! We spent most of the time outside either at the pool or at the two tables outside. I loved the comfortable outdoor furniture – couches and chairs – near the driveway. Such amazing views from there. The roman trail behind the villa was a neat path into town. I often would run (walk the steep hills) it in the mornings to get to town. Who knew you could get there that way?! So cool.
Thanks for all your help.
Much appreciated!