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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Featured Villas in Cortona and around

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

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

9.8 out of 10, Exceptional, (39)
"We loved this place! It feels very authentic and it’s so cozy. Would highly recommend to anyone."
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Private Villa with WIFI, A/C, private pool, patio, panoramic view, parking, close to Montepulciano
Dining

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

8.4 out of 10, Very good, (23)
"80 von 100 punkten. Ein sehr schönes Haus mit einem super Pool. Der Besitzer ist sehr sympathisch und hat uns frisches Gemüse gebracht, die Verwalterin ist äusserst zuvorkommend. Für den relatv hohen Preis dürfte das Mobiliar jedoch in einem besseren Zustand sein. Es hat keine bequemen Sessel im Aussenbereich um gemütlich zu sitzen, die sonnenliegen sind etwas gammlig und die Pfannen in der Küche praktisch unbrauchbar zum kochen."
Private Villa with WIFI, A/C, private pool, patio, panoramic view, parking, close to Montepulciano
I Cipressi, 5 bedrooms with pool near Cortona
Outdoor pool

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
Dining

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

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

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

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
Pool

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
Outdoor spa tub

Villa Mulino - Completely renovated old mill in Tuscany

9.8 out of 10, Exceptional, (6)
"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
Pool

Heritage Tuscan Farmhouse with private swimming pool

10.0 out of 10, Exceptional, (46)
"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.
Dining

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 Calcinaio - Holiday Country Villa with swimming pool in Cortona
Pool

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

9.2 out of 10, Wonderful, (44)
"We liked our stay very much"
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Casa Violina - Holiday Rental with private swimming pool in Valdichiana, Tuscany.
Pool

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

9.8 out of 10, Exceptional, (16)
"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 Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
Fridge, microwave, oven, stovetop

Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.

9.6 out of 10, Exceptional, (44)
"We had a very nice and relaxing time there because it is very quiet in this area. We can only recommend this property."
Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
Villa Primula - Holiday Rental in Cortona, Tuscany
Pool

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
Romantic Lux Country House
Pool

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
Outdoor pool

Beautiful villa with spectacular views in a rural location

9.8 out of 10, Exceptional, (40)
"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
Beautifully converted farmhouse alone on a tuscan hillside with stunning views
Pool

Beautifully converted farmhouse alone on a tuscan hillside with stunning views

8.6 out of 10, Excellent, (15)
"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
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
Outdoor dining

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

9.8 out of 10, Exceptional, (29)
"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
Dining

Casa Lamate

9.4 out of 10, Exceptional, (3)
"The furniture and bedding could be updated. "
Casa Lamate
Villa Margherita Due - Country villa with swimming pool in Cortona, Tuscany
Pool

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

9.4 out of 10, Exceptional, (33)
"Séjour agréable autour de la superbe piscine. Marguerite est très sympa. Mais pour nous, le prix est trop élevé par rapport aux prestations de la maison."
Villa Margherita Due - Country villa with swimming pool in Cortona, Tuscany
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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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 505 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.