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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
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12 Sept - 14 Sept
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10 Oct - 12 Oct

Featured Villas in Cortona and around

Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Relax in a serene outdoor setting with a wicker lounge chair and shaded patio area.

Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany

10.0 out of 10, Exceptional, (42)
"We spent a few nice days in spring '25 in Cortona"
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Luxury Cortona view hilltop Villa
Outdoor pool, a heated pool

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (48)
"The location and accommodations are perfect for a family. Nestled in the Italian countryside providing easy access to the nearby renaissance villages, art and landscapes and the people of Italy. The accommodations that Mieke has provided will only put a smile on your face."
Luxury Cortona view hilltop Villa
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
Stroll through the serene garden, leading to a charming traditional home with a pitched roof and multiple windows.

Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

9.8 out of 10, Exceptional, (32)
"We love our stay st Ca de Santi. Everything was great and the property is really amazing. You feel the Tuscany atmosphere."
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Stroll through the serene garden, surrounded by lush greenery and tall cypress trees, and enjoy a moment of peace by the seating area.

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

9.2 out of 10, Wonderful, (45)
"We liked our stay very much"
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
I Cipressi, 5 bedrooms with pool near Cortona
Surrounded by lush greenery, this property features a swimming pool and a two-story building with a unique roof design.

I Cipressi, 5 bedrooms with pool near Cortona

10.0 out of 10, Exceptional, (2)
"The home is beautiful: Wonderfully decorated and lovingly cared for. Views are amazing; Caretakers are lovely and we all fell in love with Zorro the Dog. My only complaint is that the beds were only box springs and could have been more comfortable."
I Cipressi, 5 bedrooms with pool near Cortona
Casale Le Vigne, 8 pax, private pool
Relax in a serene outdoor space with a thatched roof, brick wall, and comfortable lounge chairs.

Casale Le Vigne, 8 pax, private pool

10.0 out of 10, Exceptional, (9)
"Group of 9 had a fantastic stay. The villa is superbly fitted out with lovely decor and kitchen equipment. The kids loved the pool as did the adults and the evening meal area was superb. Very good communication with the host who gave us some great suggestions. Loved our holiday and the villa was exactly what we needed. Very secluded so loved watching the stars with lots of local wine."
Casale Le Vigne, 8 pax, private pool
17th-century Tuscan villa, few km from Cortona!
Outdoor pool

17th-century Tuscan villa, few km from Cortona!

17th-century Tuscan villa, few km from Cortona!
Stunning private villa with WIFI, A/C, private pool, TV, veranda, panoramic view and parking
Relax by the serene pool surrounded by a lush lawn and rustic stone wall, with rolling hills in the distance.

Stunning private villa with WIFI, A/C, private pool, TV, veranda, panoramic view and parking

10.0 out of 10, Exceptional, (1)
"This was a fabulous stay for my family! Giuseppe and Adelfa went above and beyond, actually making a beautiful fruit torta upon our return and stocking the kitchen with necessary supplies for the jet-lagged crew. The house itself is stunning, we had many beautiful Tuscan dinners under the pergola. The pool is perfect for lounging, salt water clean, grass areas up to the pool edge, incredible view of the Val d’Chiana. The cafe at Torreone run by Luca is a short walk. Thank you again for a...
Stunning private villa with WIFI, A/C, private pool, TV, veranda, panoramic view and parking
Heritage Tuscan Farmhouse with private swimming pool
Relax by the serene pool surrounded by lush greenery and breathtaking mountain views.

Heritage Tuscan Farmhouse with private swimming pool

10.0 out of 10, Exceptional, (48)
"Lovely old property with lots of history. Good size pool and lots or nice spots to sit around the house. Great restaurants not far away. Louise was an excellent host."
Heritage Tuscan Farmhouse with private swimming pool
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Experience a tranquil countryside retreat in this traditional farmhouse-style guesthouse with a central entrance and multiple rooms.

Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.

9.6 out of 10, Exceptional, (11)
"Surrounding very nice and quiet. Accomodation very comfortable and huge garden. Large Shilling pool. Everything compiled to have a very nice stay."
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Villa Mulino - Completely renovated old mill in Tuscany
Guests can enjoy a serene setting amidst lush green surroundings and manicured lawns.

Villa Mulino - Completely renovated old mill in Tuscany

9.8 out of 10, Exceptional, (7)
"Absolutely perfect. The house is immaculate, a tasteful blend of traditional and contemporary and still eminently functional. The owner should be very proud of what he has created here, he has impeccable taste and his attention to detail to ensure the comfort of his guests is an example to others. He is also an excellent host, charming, warm and genuinely concerned as to your comfort. The garden has to be at least an acre and is absolutely beautiful and not surprisingly well maintained. The pool...
Villa Mulino - Completely renovated old mill in Tuscany
Private Villa with private pool, WIFI, A/C, patio, panoramic view, parking, close to Montepulciano
Enjoy the serene views from this balcony with a table for two.

Private Villa with private pool, WIFI, A/C, patio, panoramic view, parking, close to Montepulciano

8.4 out of 10, Very good, (23)
"Everything’ we could have wished for. Wonderfully private Glorious garden Brilliant swimming pool Smiling and generous owner who could not do enough Incredibly helpful caretaker. Everything was excellent"
Private Villa with private pool, WIFI, A/C, patio, panoramic view, parking, close to Montepulciano
Beautifully converted farmhouse alone on a tuscan hillside with stunning views
Relax by the serene pool surrounded by lush green hills and a seating area with a table and chairs.

Beautifully converted farmhouse alone on a tuscan hillside with stunning views

8.8 out of 10, Excellent, (16)
"Had a good time, check in wasn't done properly. But we believe that it was a coincidence and will not happen again. Anything else was nice. The road is a bit difficult to drive on. Would recommend a car with a bit ground clearance. We are coming back most definitely."
Beautifully converted farmhouse alone on a tuscan hillside with stunning views
Casa Emma, Near Cortona, Private Pool. BBQ, Stunning views, BBand,Relax, enjoy!
Surrounded by lush greenery, this property features a main building with a tiled roof and a nearby swimming pool.

Casa Emma, Near Cortona, Private Pool. BBQ, Stunning views, BBand,Relax, enjoy!

9.6 out of 10, Exceptional, (46)
"We had a very nice and relaxing time there because it is very quiet in this area. We can only recommend this property."
Casa Emma, Near Cortona, Private Pool. BBQ, Stunning views, BBand,Relax, enjoy!
Villa Margherita Tre - Country villa with swimming pool in Cortona, Tuscany
Relax by the serene pool surrounded by lush greenery and a panoramic view of the surrounding hills.

Villa Margherita Tre - Country villa with swimming pool in Cortona, Tuscany

9.2 out of 10, Wonderful, (30)
"The villa is very cozy, it's about a 20 minutes drive from Cortona, in the middle of the country side, plan on grabbing groceries and supplies immediately. It's perfect if you want to experience a rustic simple authentic Italian country side life. We love our gift of fresh eggs the day before we left. Thanks."
Villa Margherita Tre - Country villa with swimming pool in Cortona, Tuscany
House only 4 km from Cortona, sleeps 12. Private pool, AC, Wi-Fi and small gym
Relax by the pool surrounded by lush greenery and distant hills.

House only 4 km from Cortona, sleeps 12. Private pool, AC, Wi-Fi and small gym

10.0 out of 10, Exceptional, (13)
"Massimiliano was an excellent host. Always helping to find reservations& directions. Beds are very firm. Listing failed to mention there were 2 flights of concrete stairs to 4 of the bedrooms. Excellent pool for the family."
House only 4 km from Cortona, sleeps 12. Private pool, AC, Wi-Fi and small gym
Tuscan Villa private infinity pool, exclusive location, AC, extra services
Surrounded by lush greenery, this serene pool area offers a tranquil atmosphere perfect for relaxation.

Tuscan Villa private infinity pool, exclusive location, AC, extra services

10.0 out of 10, Exceptional, (61)
"The Baldoni family were amazing hosts, from the warm welcome, to the delicious pizza dinner at their home, to their generous sharing of their culture and history. Chiara, Davide, and all the family were so welcoming and helpful. Highly recommend and hope to return some day soon."
Tuscan Villa private infinity pool, exclusive location, AC, extra services
Romantic Lux Country House
Experience the charm of a traditional European-style building with a prominent tower and secure, entrance.

Romantic Lux Country House

9.8 out of 10, Exceptional, (10)
"The picturesque setting is truly beautiful. The communication was clear, professional, kind and present. Great beds, pool, view and location. It is an easy drive to Sienna and the other Tuscan towns. Communication through the WhatsApp is helpful with the managers of the property. Thank you for a wonderful stay."
Romantic Lux Country House
Villa Giare - Villa with private pool
Relax by the serene pool surrounded by lush greenery and rolling hills.

Villa Giare - Villa with private pool

10.0 out of 10, Exceptional, (5)
"very good"
Villa Giare - Villa with private pool
Tuscan Dream: Gorgeous Private Cortona House with Fantastic Views, Garden & Pool
Dine al fresco with a scenic mountain view, surrounded by fine china and elegant table settings.

Tuscan Dream: Gorgeous Private Cortona House with Fantastic Views, Garden & Pool

10.0 out of 10, Exceptional, (20)
"We had a great and relaxing time at the villa. Nice outdoor space. The location is perfect - a short walk into Cortona and an easy drive to other towns in both Tuscany and Umbria."
Tuscan Dream: Gorgeous Private Cortona House with Fantastic Views, Garden & Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cortona Hotel Reviews

Hotel Villa Marsili

Hotel Villa Marsili

10/10 Excellent
"This hotel is wonderful! The staff is so inviting and friendly! It is in a perfect location. Very close to the city center. Highly recommend! "
Bernadette 1-night trip
Posted 2 days ago
Hotel Villa Marsili

Frequently asked questions

How much do villas in Cortona cost?
Rates for villas in Cortona range between and per night. Whatever your budget, you can find someplace that fits your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Cortona?
Cortona has 502 villas to choose from. Find a stay that's right for you quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool.
Why book your villa in Cortona with Expedia?
Use Expedia to find your ideal villa in Cortona. Taking the kids on holiday? Make the most of our helpful filters to search for stays with amenities like WiFi and a pool. If you need to stick to a budget, choose how much you're willing to spend and the star rating of the property. We'll help you find a perfect place that suits your taste and style.