Villas and Vacation Homes in Cortona

Casina Paradiso is located near Cortona, a town renowned for its Etruscan history, noble palaces, and art, and is just a short drive from Trasimeno Lake's beaches and historic centers.
This 540 sq ft holiday home, perfect for up to 3 guests, features air conditioning, Wi-Fi, a shared swimming pool with panoramic views, and a private terrace-solarium with barbecue facilities, ideal for exploring Tuscany and Umbria.

Casale Margherita is a tranquil holiday home located in Cortona, approximately 19 miles from Piazza Grande and 35 miles from Perugia Airport, with convenient access to Corso Vannucci and the Magione Motorspeedway.
This 1080 sq ft villa offers a relaxing environment for up to 7 guests, featuring 2 bedrooms, 2 bathrooms, a seasonal outdoor swimming pool, sauna (unavailable October 31, 2026 - June 5, 2026), fitness room, garden, and terrace.

House rental for 4 guests with an excellent rating of 100% based on 22 reviews. This accommodation is based in Cortona.
Services and facilities: a solarium, an iron and a fitness center. Take advantage of the terrace in this house in Cortona.

Agriturismo Fringuello - Sofora is located in Cortona, 19 miles from Piazza Grande and 30 miles from Perugia Train Station, offering a prime location for exploring the region.
This expansive 1080 sq ft villa accommodates up to 21 guests with 6 bedrooms and 5 bathrooms, featuring a stunning infinity swimming pool, a spacious terrace, a lush garden, and modern amenities including air conditioning and WiFi.

Perched on the slopes of Cortona, this 17th-century villa offers panoramic views and a direct connection to the historic hill town famously featured in 'Under the Tuscan Sun'.
This expansive 550 m2 holiday home comfortably accommodates 34 guests with 15 bedrooms, featuring air conditioning, a swimming pool, a garden, and parking for an authentic Tuscan experience.

This elegant two-story villa is located in a rural setting near Cortona, just 1 mile from the town center, with a restaurant 0.2 miles away and a grocery store 0.3 miles away.
Accommodating up to 20 guests, this luxury holiday home boasts 10 bedrooms, 11 bathrooms, a private swimming pool with a barbecue, and is fully air-conditioned with Wi-Fi throughout.

Located just outside the main town, this villa offers exclusive relaxation with a private garden and pool, providing easy access to Cortona's historic center within a short drive.
This family-friendly holiday home accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, complimentary Wi-Fi, and private parking, alongside an included free wine tasting experience.

Located in Cortona, this 45 m2 apartment offers convenient access to the town's attractions, making it an ideal base for exploring the historic district.
This welcoming holiday home features one bedroom, one bathroom, a well-equipped kitchen with a microwave and fridge, and accommodates up to two guests, perfect for a comfortable stay.

This detached chalet offers a secluded retreat in a residential villa area, located just 2 miles from the historic center of Cortona and 10 miles from the recreational opportunities at Lake Trasimeno.
This 540 square foot holiday home accommodates up to 2 guests with 1 bedroom and 1 bathroom, featuring a private 200 square meter garden with a barbecue, air conditioning, and access to a shared swimming pool on the 2-hectare property.

Centrally located in Cortona, this ground-floor apartment offers immediate access to the town's attractions and is just a short walk to grocery stores, bars, and restaurants.
This welcoming holiday home comfortably accommodates up to 3 guests with 1 bedroom and a sofa bed, featuring a fully equipped kitchen with a dishwasher, WiFi, and all utilities included.

Strategically located in Camucia-Cortona, this 2-bedroom house offers excellent access to Cortona and Tuscan gems like Perugia and Arezzo, just a short walk from the Camucia-Cortona train station.
This welcoming holiday home accommodates up to 4 guests and features a kitchen with a freezer, parking, and is an ideal base for exploring the region's renowned tourist destinations.

Enjoy this 700 sq ft house in Cortona, Italy, offering panoramic views of the Val di Chiana and conveniently located just 400 meters from the historic Etruscan town.
This welcoming holiday home features 2 bedrooms, accommodates up to 5 guests, and boasts a private swimming pool, air conditioning, Wi-Fi, and a terrace, with optional chef-prepared meals and cooking classes available.

La Limonaia Cortona is located in Cortona, 17 miles from Piazza Grande and 38 miles from Perugia San Francesco d'Assisi Airport.
This 540 sq ft villa offers 2 bedrooms, 1 bathroom, and accommodates up to 7 guests with a private swimming pool, air conditioning, and free WiFi.

Colle Degli Ulivi is located in the Cortona district, 19 miles from Piazza Grande and 24 miles from Magione Motorspeedway.
This spacious 4090 square foot villa offers 7 bedrooms, 6 bathrooms, and accommodates up to 27 guests, featuring a seasonal outdoor pool, a garden with seating, barbecue facilities, and complimentary WiFi.

Located in Cortona, Casa del Sole 4 is a luxurious villa offering elegant accommodations, situated 18 miles from Piazza Grande and 22 miles from Magione Motorspeedway.
This family-friendly holiday home features a swimming pool with a view, a garden, air conditioning, a terrace, and a fully equipped kitchen, with free on-site private parking available for guests.

Set within a two-hectare olive grove, this villa offers unparalleled panoramic views of Cortona from its tranquil, elevated position, just 3 miles from the historic town center and convenient to Tuscan and Umbrian cultural hubs.
This spacious 1830 sq ft holiday home accommodates up to 8 guests across 3 bedrooms and 5 bathrooms, featuring a private fenced swimming pool, a large garden with barbecue and wood-burning oven, air conditioning, and internet.

Located in a peaceful residential area, this chalet offers a quiet retreat 2 miles from Cortona's historic center and 10 miles from Lake Trasimeno, with convenient access to Castiglion Fiorentino (13 miles) and Passignano sul Trasimeno (20 miles).
This welcoming 700 sq ft holiday home, perfect for two guests, features air conditioning, a kitchenette, a private 200 sq meter garden with a barbecue, and access to a shared seasonal swimming pool, making it an ideal villa for exploring the region.

Offering panoramic views, this independent villa is located just outside Cortona's town center, providing convenient access to its historical attractions.
This luxurious 2690 sq ft holiday home accommodates up to 10 guests with 5 bedrooms and 4 bathrooms, featuring air conditioning, Wi-Fi, a private pool, garden with outdoor dining, and complimentary wine tasting.

Farm rental for up to 5 people. Your accommodation will be located in Cortona.
Services and facilities: free parking, a restaurant and rooms suitable for events. Take advantage of the air conditioning in this accommodation in Cortona.

Surrounded by fields, this detached country house is located 3 miles from Cortona's center and 13 miles from Lake Trasimeno.
This expansive 3,800 square foot villa, featuring 8 bedrooms and 7 bathrooms, offers a private garden with a 6x12 meter swimming pool, air conditioning, and a cook service available upon request.