Holiday Rentals in Cortona

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Holiday Rentals in Cortona

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (64)
"Property is perfect for the view and the loction"
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (62)
"Firstly, the property was absolutely perfect. It was big, all air conditioned (when it’s so hot outside it needs to be) and really felt like a home from home. All the bedrooms are big and the shutters make it super dark at nighttime for sensitive sleepers. It had everything that we needed and more, with lots of different areas to sit and relax. The pool was beautiful, larger than I was expecting and a great infinity effect as you look over at Cortona. The location was great. Close enough to...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Outdoor dining
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
9.8 out of 10, Exceptional, (7)
" The introduction to the apartment by the agent was really nice. maybe take a moment with non Europeans and explain how the stove works. Kitchen great. Well stocked to get started. Bathroom great bedroom good. Bed great. Location easy in and out of the city. Great. View, phenomenal. Beyond great. The only disconcerting thing about this house is there isn't anyplace to really sit and relax in comfort. I would highly recommend the owner replace the furniture in the sitting parlor with some...
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Casa Nobile - a noble apartment few steps from the main square
Interior
Casa Nobile - a noble apartment few steps from the main square
Casa Nobile - a noble apartment few steps from the main square
Panoramic View Village of Villa Luigina Cortona
Property grounds
Panoramic View Village of Villa Luigina Cortona
Panoramic View Village of Villa Luigina Cortona
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
Pool
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
7.4 out of 10, Good, (3)
"Un luogo che ha lasciato tutti noi (sia adulti che bambini) a bocca aperta: un paradiso terrestre! Per chi ama la natura, vuole staccare dalla caotica vita quotidiana e godere del tempo con i propri cari , questo è il posto che offre tutto ciò e di più! Non conoscendo bene la zona siamo arrivati un po’ impreparati ma tutto si è risolto con un viaggio al supermercato vicino Cortona! *essendo immersi nella natura c’è’ da far conto di insetti e possibili cervi e cinghiali, che rendono questo posto...
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
La Torretta - downtown Cortona, on the second floor of a noble palazzo
Microwave, oven, dishwasher, coffee/tea maker
La Torretta - downtown Cortona, on the second floor of a noble palazzo
10.0 out of 10, Exceptional, (4)
"Very roomy, well equipped, and a really good location. Would stay again!"
La Torretta - downtown Cortona, on the second floor of a noble palazzo
Cottage " I due Pini"
Outdoor dining
Cottage " I due Pini"
10.0 out of 10, Exceptional, (36)
"Beautiful location in a natural environment. Wonderful hosts, and I especially liked their dog Akila who is very friendly."
Cottage " I due Pini"
Villa Primula - Holiday Rental in Cortona, Tuscany
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
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)
"Nice enough property, very clean. You need to reconfigure furniture in living room so more people can sit. Ok for 2 people but not really inviting and comfortable. Don't need the dining table in that room or that huge hutch. More wine glasses and bowls needed. Update master bedroom mattress. Very uncomfortable. Grounds very enjoyable! Property manager very responsive and helpful. Not really walkable up to hilltop. Reason for the lower rating is the house is over 200 years old...
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
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
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)
"Fabulous location and property. We had a fantastic family holiday in the house. Great area to explore. Madeline was lovely. We will be back"
Beautiful villa with spectacular views in a rural location
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Outdoor dining
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
9.8 out of 10, Exceptional, (53)
"We spent the summer in Cortona at Il Roseto. Our family of four, plus my mother. It was a dream. The apartment is so lovely and perfectly situated, close to everything, yet tucked away in a quiet spot. The outdoor terrace is filled with roses and fragrant shrubs. Fernando and Pierfrancesco responded quickly to every question or need. Il Roseto was truly our home, and it felt that way. The apartment was recently renovated with new foam mattresses and pillows, and AC mini splits and smart TVs in...
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Heritage Tuscan Farmhouse with private swimming pool
Pool
Heritage Tuscan Farmhouse with private swimming pool
10.0 out of 10, Exceptional, (44)
"We had a very happy stay at this house in the country with our two friends. It is ideally located within an hour’s drive of interesting sites and historic towns. The place and its surroundings allowed us a restful and pleasant respite from our busier daytrips. The house was comfortable, beds were very good and the garden provided a peaceful setting with a choice of sitting and lounging areas. Louise was lovely, an excellent hostess who responded quickly to our questions and needs. "
Heritage Tuscan Farmhouse 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)
"This property is all it explains to be. The stay included myself, my husband, my daughters and their families. The property is spectacular, the rooms as beautiful as shown. The guesthouse was perfect for my daughter, her husband and 2 young children. The travel cots were perfect and opening the chest of toys brought so much joy to my 2 year old granddaughter. We utilized the kitchen and pizza oven and have such wonderful memories to hold. Our only disappointment was that the pool heater was not...
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
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)
"Having vacationed in this area for the last 20 years and lived here for four, rarely have we come across a restoration with the attention to detail and clearly a personal touch from someone passionate about this special place. A beautifully restored farmhouse interior with plenty of space and good size rooms all finished to a high standard. The living room especially is a comfortable and inviting escape when it’s too hot outside. The outside areas and furniture could do with some renewal to...
Beautifully converted farmhouse alone on a tuscan hillside with stunning views
Luxury Peaceful Villa With Vine Covered Pergola Enjoying Panoramic Views.
Exterior
Luxury Peaceful Villa With Vine Covered Pergola Enjoying Panoramic Views.
10.0 out of 10, Exceptional, (34)
"House was lovely. Great views. Only downside was the difficult drive up to the property and the driveway which was very hard to get the car up and down."
Luxury Peaceful Villa With Vine Covered Pergola Enjoying Panoramic Views.
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)
"We were a family group of 15 ranging in age from 20 to 92. We used the pool every day. Laughed at the clothes dryer because they have the same kind in Portugal where we vacationed. Many people walked into Camucia and enjoyed the restaurants grocery stores etc. Several of us have been to Italy before my first time in Assisi but we shared experiences with them. Staff was prompt to arespond to any problems. And a week of perfect weather makes it all the better"
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
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, (20)
"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
City / Village Apartment in Cortona with 2 bedrooms sleeps 4
Outdoor dining
City / Village Apartment in Cortona with 2 bedrooms sleeps 4
10.0 out of 10, Exceptional, (62)
"Absolutely amazing, villa is impeccable, location is perfect, the view is stunning and the people who take care of this place are true friends! Whenever we come back in Cortona, we’ll definitely come say hi! We would’ve stayed another month for sure. You can trust this place, you won’t regret it…"
City / Village Apartment in Cortona with 2 bedrooms sleeps 4
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 types of properties in Cortona you may be interested in

Monastero di Cortona Hotel & Spa
Sauna, hot tub, steam room, massages
Monastero di Cortona Hotel & Spa
5.0 star property
10.0 out of 10, Exceptional, (199)
"I would prefer if they had an option to include the spa in the package rather than having to pay separately. Everything else was phenomenal "
Monastero di Cortona Hotel & Spa
Villa di Piazzano - Small Luxury Hotel of the World
Courtyard
Villa di Piazzano - Small Luxury Hotel of the World
5.0 star property
9.8 out of 10, Exceptional, (200)
"The Villa di Piazzano is stunning down to the smallest detail. The staff is attentive, pleasant and helpful. The food and wine at the onsite restaurant was some of the best we had on our 23-day trip across Italy. One of our favorite stays for sure!"
The price is €517
includes taxes & fees
5 Nov - 6 Nov
Villa di Piazzano - Small Luxury Hotel of the World
Hotel San Luca
View from property
Hotel San Luca
4.0 star property
8.6 out of 10, Excellent, (405)
"This hotel is in the perfect location and has amazing views! The breakfast was very good! Would definitely stay here again. "
The price is €95
includes taxes & fees
5 Nov - 6 Nov
Hotel San Luca
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

Can I find holiday rentals in Cortona?

Yes, there are holiday rentals close to the most popular sights in Cortona, or you can select a more 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 theatre during your trip.

How many holiday rentals are there in Cortona?

With 266 Expedia holiday rentals, you're guaranteed to find just the right place for your Cortona stay.

What’s there to see and do in Cortona?

Cultural attractions include Museum of the Etruscan Academy and Signorelli Theatre, whereas Val di Chiana is one spot to enjoy nature. While here, Piazza della Repubblica and Cortona Cathedral are other places worth a visit.

What’s a holiday rental in Cortona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cortona. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips or small group gatherings.