Cortona Vacation Rentals

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Vacation Rentals in Cortona

Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (55)
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
View from property
Cortonas Rooftop Nest
10.0 out of 10, Exceptional, (5)
"Our recent stay in Cortona was pure bliss. The apartment boasted expansive views of the picturesque town, complemented by tasteful furnishings and a fully equipped, spacious kitchen. The Wi-Fi was top-notch, perfect for both work and leisure. Margherita, our charming host, was a delight. Fluent in English, she was always available and attentive to our needs. Highly recommend this gem for an unforgettable Tuscan experience."
The price is CA $220
CA $252 total
includes taxes & fees
May 21 - May 22
Cortonas Rooftop Nest
Exterior
Cottage " I due Pini"
10.0 out of 10, Exceptional, (35)
"Beautiful location in a natural environment. Wonderful hosts, and I especially liked their dog Akila who is very friendly."
Cottage " I due Pini"
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Fridge, microwave, oven, stovetop
Vintage Villa Vagnucci - Cortona
10.0 out of 10, Exceptional, (1)
"Have stayed in area before, but not Cortona. We were taken around the property by Nonna and her grandson. A great team. They bogg live on siteNonna was attentive but not intrusive, and always left us tomatoes and basil from her garden, but spoke no english - more of a comment about us than her as it would have been great to talk to her more fully. A lovely lady. Stefano was great as translator, go to guy for info - taxi firms, air con specialists, bar to watch womens footy final! Etc A great...
Vintage Villa Vagnucci - Cortona
Indoor pool, outdoor pool
Private Pool & Cottage for 6 in Secluded Hamlet Spectacular Views 7 km to Corton
10.0 out of 10, Exceptional, (8)
"We were greeted upon arrival by Rafaello, our host, who was very helpful in getting us situated for our 5 night stay. The house is lovely, surrounded by the olive trees. The pool is pristine because Raffi comes to clean it every day. We did laundry in the unique washer and hung out the clothes on the drying rack that was provided. The views of the Tuscan countryside are lovely. Central location makes it easy to visit other Tuscan towns like Cortona, Siena, Montepulciano. I would recommend this...
Private Pool & Cottage for 6 in Secluded Hamlet Spectacular Views 7 km to Corton
Outdoor dining
Charming small villa near Cortona,garden,olive grove.A/C.Fiber Wifi -LA COLONICA
10.0 out of 10, Exceptional, (132)
"La Colonica is large and beautifully furnished - we only used one, but there are 2 large double bedrooms with showers. The hosts are very friendly, and David is English, so no communication problems. We were free to roam about the grounds - there is an olive grove attatched. There is an enormous, friendly dog who leaves white hairs all over you! The only drawback is that in the village (very picturesque) there are only 2 places to eat - 1 pizzeria and 1 restaurant. Apart from that the place is...
Charming small villa near Cortona,garden,olive grove.A/C.Fiber Wifi -LA COLONICA
Pool
Belvilla by OYO Sparsa Girasole
10.0 out of 10, Exceptional, (1)
Belvilla by OYO Sparsa Girasole
Exterior
Gorgeous Comfortable House with Garden & Pool - Its all yours.
10.0 out of 10, Exceptional, (15)
"We loved our stay at “Villa Rosa”. The owner was very informative and provided all the detail and recommendations we would ever need. Alex the property manager was there to greet us to show us around and later provided further answers. The Villa is very comfortable with all the amenities you could possibly need. Great Wi-fi too. We enjoyed particularly the pool area which is very private and secluded with great views over the rolling hills. My husband is a keen wildlife enthusiast, so he was...
Gorgeous Comfortable House with Garden & Pool - Its all yours.
Pool
Belvilla by OYO Loggia
10.0 out of 10, Exceptional, (7)
Belvilla by OYO Loggia
Property grounds
Nice apartment for 6 guests with pool, WIFI, TV and parking
10.0 out of 10, Exceptional, (4)
"Liebevoll restauriertes, landestypisches Haus. Sehr sauber, Vermieter immer freundlich und hilfsbereit. Landschaftlich top."
Nice apartment for 6 guests with pool, WIFI, TV and parking
Pool
Heritage Tuscan Farmhouse with private swimming pool
10.0 out of 10, Exceptional, (39)
"We had a lovely holiday at Villa Rasenna. Louise is a great host and was very helpful and replied very quickly to any queries. The kitchen is well equipped and the sitting area comfortable and homely. We made good use of the pool. We enjoyed a great meal in the villa cooked by Elena and a local wine tasting and pizza in the village. There are lovely walks from the villa in the local countryside. Would definitely recommend a holiday and we would love to return. Thanks Louise."
Heritage Tuscan Farmhouse with private swimming pool
Property grounds
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
10.0 out of 10, Exceptional, (40)
"What a beautiful place to enjoy Christmas with family. The villa is beautiful, comfortable and has a well stocked kitchen with everything you could need. The views are amazing and we watched the New Year fireworks from the sitting room. Denise did an amazing job buying all of our groceries for our arrival. Mieke is a wonderful host - responsive and patient, answering all of our questions. We hope to come back in the summer one day."
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
Outdoor dining
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (54)
"This is a wonderful property in a quiet area, but only a short walk to the piazza and restaurants. The only improvement I would recommend is the shower caddy; all of my travel sized items kept falling out of it."
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
La Finestra sul Teatro
9.8 out of 10, Exceptional, (29)
"This unit met and exceeded our expectations! The host was extremely friendly and helpful, and this well-stocked home has a perfect location within the best area of Cortona. I highly recommend this unit to anyone wishing for a clean, 'light & bright' home within walking distance to everything you would ever want to do here. Thank you, Rossana, for sharing your home with us, we look forward to our next visit!"
The price is CA $214
CA $310 total
includes taxes & fees
Jun 2 - Jun 3
La Finestra sul Teatro
Fridge, microwave, oven, stovetop
Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
9.8 out of 10, Exceptional, (40)
"We had a fantastic week in this lovely villa. It really does have everything you could possibly need - a real home from home. Lots of lovely spaces inside and out to enjoy. We loved sitting out in the evenings having dinner and we’re lucky to be there during the Perseus meteor shower and saw lots of shooting stars in the clear skys. We also ate out in the lovely town of Cortona - la buccia with beautifully presented food and a couple of more casual restaurants which were also excellent. The...
Villa Gioia near Cortona, Private Pool,Bband,bbq,stunning views.
Pool
Beautiful villa with spectacular views in a rural location
9.8 out of 10, Exceptional, (35)
"We absolutely loved our stay! Hosted by Madeleine and her son Phillip who are both lovely and super helpful, this place is rural and quiet. The views are stunning and the house is well equipped and comfortable. It's a drive to the shops but so worth it for the peaceful location!"
Beautiful villa with spectacular views in a rural location
Exterior
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
9.8 out of 10, Exceptional, (52)
"The property was built in 1500 but updated recently. It definitely has its quirks related to gas and electricity. More written instructions in the home would be useful. The home is spacious with the exception of the galley style kitchen. There is a lovely courtyard that seems to be very unique to properties within the walls of Cortona. There are a couple of nice walks around Cortona. You are not too far from Sienna for a day trip."
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Fridge, microwave, oven, dishwasher
Prestigious apartment with panoramic terrace, located in the center of Cortona.
9.6 out of 10, Exceptional, (4)
"This is a great home, perfect location (close to parking and walk to everything) and really nice and thoughtful manager!!!"
Prestigious apartment with panoramic terrace, located in the center of Cortona.
Pool
Villa Primula - Holiday Rental in Cortona, Tuscany
9.6 out of 10, Exceptional, (45)
"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
A heated pool
Villa Mulino - Completely renovated old mill in Tuscany
9.6 out of 10, Exceptional, (4)
Villa Mulino - Completely renovated old mill in Tuscany
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See all available properties in Cortona
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.

Cortona Vacation Rental Travel Info

Other types of properties in Cortona you may be interested in

Sauna, spa tub, steam room, massages
Monastero di Cortona Hotel & Spa
5.0 star property
10.0 out of 10, Exceptional, (166)
"Excellent experience!!! Very attentive staff in ALL areas. Room was beautiful!! Breakfast was outstanding!!! Spa space was amazing!!!! A few tight corners but well worth the drive!!!! Love, love, loved the stay! "
The price is CA $449
CA $506 total
includes taxes & fees
May 22 - May 23
Monastero di Cortona Hotel & Spa
Courtyard
Villa di Piazzano - Small Luxury Hotel of the World
5.0 star property
9.8 out of 10, Exceptional, (174)
"Absolutely amazing"
The price is CA $786
CA $876 total
includes taxes & fees
May 26 - May 27
Villa di Piazzano - Small Luxury Hotel of the World
Panoramic Studio Suite, 1 Bedroom, Terrace, Valley View | Terrace/patio
Hotel San Michele
4.0 star property
9.0 out of 10, Wonderful, (223)
"Amazing breakfast buffet. "
The price is CA $177
CA $206 total
includes taxes & fees
Jun 9 - Jun 10
Hotel San Michele
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cortona. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Cortona?

Yes, there are vacation rentals close to the most popular sights in Cortona, or you can go with a secluded option if you're looking for a relaxing stay. Cortona is known for its cathedral and monuments. Make sure you have time to check out the temples and musical theater during your trip.

What are some of the best vacation home rentals that Cortona has to offer?

Podere Casorbica with free parking, large garden, swimming pool.: Visitors give good reviews to this Cortona vacation home rental, which is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a spa tub so you can immerse yourself in your vacation. Another good choice for your trip to Cortona is Nice house in the country of Cortona..

How many vacation rentals are there in Cortona?

With 275 Expedia vacation rentals, you're sure to find just the right place for your Cortona stay.

What’s there to see and do in Cortona?

Enjoy the outdoors at Lake Trasimeno and Val di Chiana, or simply take in cultural attractions like Signorelli Theatre and Museum of the Etruscan Academy. While here, Piazza della Repubblica and Cathedral of Cortona are other places worth a visit.

What’s a vacation rental in Cortona like?

A vacation rental is a private property where you can stay for a long or short time in Cortona. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.

Recent reviews of Cortona properties
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