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Check prices for these dates

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8 Aug - 10 Aug
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15 Aug - 17 Aug
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29 Aug - 31 Aug
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26 Sept - 28 Sept

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

9.8 out of 10, Exceptional, (40)
"This is a lovely, updated home in a fantastic location to use as base for Tuscan/ Umbrian day trips. The town of Camucia has all conveniences, many within walking distance including groceries, restaurants and the train station (@ 10 min). Cortona is a short drive up the hill. We spent most evenings in the house and really appreciated the comfortable living area. The kitchen was well equipped for any meal but we mainly used it for morning coffee/breakfast. It was too early in the season to use...
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
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
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
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, (1)
"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
Beautiful 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.

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

10.0 out of 10, Exceptional, (1)
"A beautiful estate with a stunning view."
Beautiful private villa with WIFI, A/C, private pool, TV, veranda, panoramic view and parking
Luxury Cortona view hilltop Villa
Outdoor pool, a heated pool

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (47)
"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
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
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
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.
Casa Violina - Holiday Rental with private swimming pool in Valdichiana, Tuscany.
Relax by the serene pool surrounded by lush greenery and a distant mountain range.

Casa Violina - Holiday Rental with private swimming pool in Valdichiana, Tuscany.

9.6 out of 10, Exceptional, (17)
"The booking service was excellent and they were very helpful. Excellent Villa and pool. Very clean and tidy. Owners supplied us with fruit & veg!! Will recommend to friends."
Casa Violina - Holiday Rental with private swimming pool in Valdichiana, Tuscany.
Villa Primula - Holiday Rental in Cortona, Tuscany
Enjoy al fresco dining or relaxation on the balcony with a garden view.

Villa Primula - Holiday Rental in Cortona, Tuscany

9.6 out of 10, Exceptional, (46)
"A great villa for a 3 generation group; lovely pool and garden with plenty of outside furniture. Cafes, shops and transport are within walking distance. Spacious rooms and well equipped kitchen. Owner very helpful."
Villa Primula - Holiday Rental in Cortona, Tuscany
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
Casa Emma Near Cortona, Private Pool. BBQ, Stunning views, BBand,Relax and enjoy
Surrounded by lush greenery, this property offers a, residential setting with a swimming pool.

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

9.6 out of 10, Exceptional, (45)
"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 and enjoy
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
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
Beautiful villa with spectacular views in a rural location
Relax by the rectangular pool surrounded by lush greenery and a stone patio.

Beautiful villa with spectacular views in a rural location

9.8 out of 10, Exceptional, (41)
"We had a very nice break at a wonderful place with a unique view. We would come back at any time."
Beautiful villa with spectacular views in a rural location
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, (30)
"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
Casa Lamate
Experience the charm of a traditional stone building with a well-maintained courtyard and potted plants.

Casa Lamate

9.4 out of 10, Exceptional, (3)
"The furniture and bedding could be updated. "
Casa Lamate
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Gorgeous hotel, very helpful and friendly staff, stunning pool and spa. Loved everything about this hotel! Just know that it’s an uphill walk to get there from the town center. "
Jordan 2-night trip
Posted 6 days ago
Monastero di Cortona Hotel & Spa

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.