Cortona Summer Rentals, Cottages & Cabins

There are a lot of options in Cortona. If you plan on staying in the Cortona area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Cortona:

• Monastero di Cortona Hotel & Spa
• Your Holiday Under the Tuscan Sun
• Tuscan Villa private infinity pool, exclusive location, AC, extra services
• Luxury Cortona view hilltop Villa
• Cortona Farmhouse in Tuscany - Casa Sant'Angelo
• Cottage " I due Pini"
• Wonderful villa for 6 guests with pool, WIFI, A/C, TV and panoramic view
• Beautifully restored 16th C farmhouse w/exclusive pool, woodlands, olive groves
• Tuscany as it once was
• Vacation apartments in the countryside near Cortona

In 2026, Treehouse Rental offers 1389 summer rentals in or around Cortona. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.

The average price per night for a summer rental in Cortona is $447. Check the full list of summer accommodations in Cortona.

There are 1389 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Treehouse Rental.

Yes, here are some popular summer holiday rentals in Cortona that have a private or indoor pool:

• "Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
• B&B Gabri
• Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
• Built in 1251 yet totally remodeled in 2014- Located in Historic Cortona City

Check all holiday rentals with a pool in Cortona on Treehouse Rental.