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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 534 Villas in Cortona with updated reviews, rates, and availability.

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

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

8.2 out of 10, Very Good, (21)
"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, private pool, A/C, patio, panoramic view, parking, close to Montepulciano
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, (43)
"We liked our stay very much"
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
I Cipressi, 5 bedrooms with pool near Cortona
Outdoor pool

I Cipressi, 5 bedrooms with pool near Cortona

I Cipressi, 5 bedrooms with pool near Cortona
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.

9.4 out of 10, Exceptional, (10)
"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 La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Pool

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

10.0 out of 10, Exceptional, (37)
"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
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
Casale Le Vigne, 8 pax, private pool
Interior

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

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

10.0 out of 10, Exceptional, (1)
"A beautiful estate with a stunning view."
Stunning private villa with private pool, A/C, WIFI, TV, veranda, panoramic view and parking
Rustic Farmhouse for 8+2 person with Private Swimming Pool
Outdoor dining

Rustic Farmhouse for 8+2 person with Private Swimming Pool

9.8 out of 10, Exceptional, (35)
"We had a pleasant time at the nice old house. The place has a lot of space and even with a bunch of people there are enough littleS places to have a quiet time for themselves. Mauro was a very nice and helpful host, and his sister cooked Tuscan food for us - delicious!"
Rustic Farmhouse for 8+2 person with Private Swimming Pool
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
Outdoor dining

Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool

10.0 out of 10, Exceptional, (46)
"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,great for families/groups; A/C & heatable pool
Heritage Tuscan Farmhouse with private swimming pool
Pool

Heritage Tuscan Farmhouse with private swimming pool

10.0 out of 10, Exceptional, (44)
"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
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 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)
"Perfect relaxing vacation!"
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv
Typical house with large pool and lovely views
Pool

Typical house with large pool and lovely views

9.4 out of 10, Exceptional, (12)
"A very spacious house with spacious and very clean and airconditioned rooms, fresh sheets and towels, an enormous swimmingpool, great views over the valley, perfect surroundings with beautiful villages and to top it off a visit of a small fox late at night: all great! The long, steep and slippery climb is something to consider for small cars or cars pulling trailers and the kitchen could use an update, but that's minor compared to all the advantages."
Typical house with large pool and lovely views
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)
"We enjoyed our stay very much. Everything is perfect. The "
Villa Mulino - Completely renovated old mill in Tuscany
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 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)
"Very nice quiet stay with amazing view and pool"
Villa Margherita Tre - Country villa with swimming pool in Cortona, Tuscany
Stunning private villa for 5 guests with WIFI, private pool, pets allowed and parking
Outdoor dining

Stunning private villa for 5 guests with WIFI, private pool, pets allowed and parking

9.4 out of 10, Exceptional, (13)
"Un cadre idyllique au milieu des oliviers de la vigne et des figuiers. Une petite maison typique avec le strict minimum (dont des ventilateurs), une vue magique et une piscine (sans escaliers) très bien. Le chemin d’accès ne doit pas vous décourager !"
Stunning private villa for 5 guests with WIFI, private pool, pets allowed and parking
Belvilla by Oyo Villa Letizia
1 bedroom, WiFi

Belvilla by Oyo Villa Letizia

8.0 out of 10, Very Good, (8)
"This house really gives you the Tuscan feel and Luca the owner is an amazing cook. Everything was perfect!!"
Belvilla by Oyo Villa Letizia
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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Other property types in Cortona

Casa Bacco - private house with a remarkable garden in the centre of Cortona
Outdoor dining

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (5)
"This home was outstanding from the moment we arrived. There were 6 adults and we had plenty of room to gather together. The courtyard is lovely for early morning coffee or evening wine. Close to everything that Cortona offers."
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Casa Fontelunga, Tuscan holiday villa with private pool
Outdoor pool

Casa Fontelunga, Tuscan holiday villa with private pool

9.4 out of 10, Exceptional, (8)
"We had a two week escape in the Tuscan countryside. We enjoyed touring around the area and a organized cooking class"
Casa Fontelunga, Tuscan holiday villa with private pool
Appartamento Loggetta
Apartment, 1 Bedroom | View from room

Appartamento Loggetta

Appartamento Loggetta
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.

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 534 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 vacation? 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.