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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 237 Vacation Homes in Cortona with updated reviews, rates, and availability.

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)
"Very thoughtfully restored old Villa just minutes from Cortona . The house and grounds are exactly as pictured. The very private road that leads there is a bit rough and seems very remote at first but after you venture out once you see that every convenience is minuets away and beautiful Cortona as well. A car is a good idea if you plan to go around Tuscany. 2 trains in town go everywhere but it helps to get to train and town with a car. The host is very responsive and hands on."
Casa Fontelunga, Tuscan holiday villa with private pool
Podere Casorbica with free parking, large garden, private pool.
Exterior

Podere Casorbica with free parking, large garden, private pool.

9.4 out of 10, Exceptional, (13)
"The property was lovely. Wifi was intermittently availble throughout our stay."
Podere Casorbica with free parking, large garden, private pool.
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Dishwasher, coffee/tea maker, toaster

Casa delle Rose: charming house with stunning balcony in the heart of Cortona

9.8 out of 10, Exceptional, (9)
"We travelled to Italy for 2 weeks and visited Venice, Florence, Cortona and Rome. Our most favorite stay was without a doubt was this home in Cortona. It was exactly as described and we loved the location. Only downside is parking. If you have a car, you will be lugging your luggage uphill for a good ways from the parking area. "
Casa delle Rose: charming house with stunning balcony in the heart of 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
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Living area

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

10.0 out of 10, Exceptional, (4)
"Our two adult children who were studying abroad met us here with our younger two children. We had two nights in a 12 day stay in Italy. Of all our stops, this was by far our favorite. The house was like a story book. The garden was so lovely, we spent an afternoon eating and sharing a bottle of wine. We were here in November and the weather was very mild compared to Chicago winters. Most of the stores and restaurants were open with far less people. We weren’t really here to see anything, we were...
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
3 bedrooms, iron/ironing board, WiFi, bed sheets

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

9.8 out of 10, Exceptional, (55)
"H"
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
beautiful tuscan villa with pool, ideal for groups
Terrace/patio

beautiful tuscan villa with pool, ideal for groups

10.0 out of 10, Exceptional, (25)
"A wonderful property, submerged in beautiful natural surroundings, the flora and fauna were fantastic. Our whole family were delighted by the swifts, starlings and kestrels nesting at the property, my parents described the place as simply magical. Wonderful location for my Father's 80th birthday celebrations, John and Sabine are welcoming and warm hosts. We all felt very relaxed in this comfortable, spacious home. The outside is as well equipped as inside with lots of seating and a great pool...
beautiful tuscan villa with pool, ideal for groups
Small stone farmhouse overlooking Cortona with private pool and garden
Pool

Small stone farmhouse overlooking Cortona with private pool and garden

9.0 out of 10, Wonderful, (4)
"Lovely renovated country house with olive grove outside the door and large swimming pool (which we didn't use because it was too cold). It was very clearly someone else's house, with many personal effects, photos, etc. which was a bit strange. The parking was terrible, across the street on a steep hill, with plenty of slippery mud from recent rains. It was difficult to pull out of the mud/gravel area onto the paved road. This was not made clear at all until we arrived at the house with the...
Small stone farmhouse overlooking Cortona with private pool and garden
La Pergola typical Tuscan house with wonderful view
Interior

La Pergola typical Tuscan house with wonderful view

10.0 out of 10, Exceptional, (10)
"Our stay at the villa was relaxing, and peaceful. A great central location for the Tuscan area and Cortana. We walked the trails, visited and emerged ourself into the history and surrounding countryside of beauty. Surrounded by olive trees, beautiful wildflowers and the charm of the villa gives you a true feel for the culture. "
La Pergola typical Tuscan house with wonderful view
The Old Fashion House
Smart TV, fireplace

The Old Fashion House

10.0 out of 10, Exceptional, (4)
"Newly renovated plus old world charm. Ideal location just a few steps from Piazza Garibaldi, this roomy apartment has been outfitted with every convenience, including air conditioning and a washing machine. We stayed for two weeks and hated to leave!"
The Old Fashion House
Pet friendly home in Cortona with WiFi
2 bedrooms, iron/ironing board, travel crib, free WiFi

Pet friendly home in Cortona with WiFi

10.0 out of 10, Exceptional, (1)
"Wir haben die Zeit hier sehr genossen, tolles Haus, tolle Gastgeber"
Pet friendly home in Cortona with WiFi
4 bedroom amazing home in Cortona
Fridge, microwave, stovetop, dishwasher

4 bedroom amazing home in Cortona

4 bedroom amazing home in Cortona
Casa Vinalia inside the Etruscan walls of Cortona
Fridge, microwave, oven, stovetop

Casa Vinalia inside the Etruscan walls of Cortona

10.0 out of 10, Exceptional, (4)
"We rented this house for a month. We loved it here and felt very comfortable calling it home for so long. Fully renovated with modern appliances just as pictured. Kitchen is equipped with everything you need to cook a meal, which we did 1/2 the time. Beds are comfortable and bathrooms big. Washer / dryer was a plus. Walking up and down the hills kept us in great shape to eat all the pasta we wanted! From here, we traveled by train to Florence, Lake Trasimeno, Arezzo. Owner was quick to respond...
Casa Vinalia inside the Etruscan walls of Cortona
Holiday home in Cortona with pool
Property grounds

Holiday home in Cortona with pool

10.0 out of 10, Exceptional, (12)
"Very well equipped property. The host is absolutely lovely and very helpful. "
Holiday home in Cortona with pool
Stunning Town House Cortona, Tuscany. Private Courtyard & Rooftop Terrace
Smart TV, fireplace, books

Stunning Town House Cortona, Tuscany. Private Courtyard & Rooftop Terrace

Stunning Town House Cortona, Tuscany. Private Courtyard & Rooftop Terrace
I Mandorli 8, Emma Villas
5 bedrooms, desk, iron/ironing board, free WiFi

I Mandorli 8, Emma Villas

I Mandorli 8, Emma Villas
Cosy cottage with large private pool and perfectly mantained garden - 2-BR
Pool

Cosy cottage with large private pool and perfectly mantained garden - 2-BR

9.0 out of 10, Wonderful, (2)
"The management company welcomed us to the property. The amenities were excellent with a private swimming pool. Written instructions for the washing machine, dishwasher and garbage disposal would have been helpful"
Cosy cottage with large private pool and perfectly mantained garden - 2-BR
"Gabolandia", a holiday home in Cortona
4 bedrooms, iron/ironing board, free WiFi, bed sheets

"Gabolandia", a holiday home in Cortona

9.2 out of 10, Wonderful, (5)
"We were pleasantly suprised by the hospitality of our hosts - nothing was an exra mile for them in trying to help or please their guests. Many special thanks to Marzia and Massiamo and all their big and friendly family for being the wonderful hosts. The house we stayed in is spacious and clean and had everything we need. The place is a real countryside gem - quiet and full of active leasure options. We really enjoyed our holiday at this place and would recommend it to anyone wishing a restful...
"Gabolandia", a holiday home in Cortona
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
Outdoor pool

Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

9.6 out of 10, Exceptional, (4)
"The villa was so comfortable and lovely. Michele was very responsive and helpful. 10/10 experience."
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
Maya Luxury Home - private garden for breathtaking view, nearby the centre
Living area

Maya Luxury Home - private garden for breathtaking view, nearby the centre

10.0 out of 10, Exceptional, (4)
"A wonderful short break and Isabella and her team were exceptionally kind and very helpful. They even helped us with car hire as another company had tried to rip us off yet these guys were very kind and genuine. Can highly recommend."
Maya Luxury Home - private garden for breathtaking view, nearby the centre
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

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Terrace/patio

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

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

10.0 out of 10, Exceptional, (4)
"Our two adult children who were studying abroad met us here with our younger two children. We had two nights in a 12 day stay in Italy. Of all our stops, this was by far our favorite. The house was like a story book. The garden was so lovely, we spent an afternoon eating and sharing a bottle of wine. We were here in November and the weather was very mild compared to Chicago winters. Most of the stores and restaurants were open with far less people. We weren’t really here to see anything, we were...
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)
"Very thoughtfully restored old Villa just minutes from Cortona . The house and grounds are exactly as pictured. The very private road that leads there is a bit rough and seems very remote at first but after you venture out once you see that every convenience is minuets away and beautiful Cortona as well. A car is a good idea if you plan to go around Tuscany. 2 trains in town go everywhere but it helps to get to train and town with a car. The host is very responsive and hands on."
Casa Fontelunga, Tuscan holiday villa with private pool
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.