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Villas Cortona to rent

We have 31 properties to choose from.
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House Castroncello
800 m² house ∙ 18 guests ∙ 9 bedrooms

House Michelangioli

Castroncello, Castiglion Fiorentino, Italy
from £826
per night
5.0
Outstanding
(20 ratings)
from £826
per night
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House Cortona
318 m² house ∙ 12 guests ∙ 6 bedrooms

House Antico Duomo

Cortona, Province of Arezzo, Italy
from £292
per night
from £292
per night
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Apartment Cortona
38 m² apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Antico Duomo

Cortona, Province of Arezzo, Italy
from £78
per night
from £78
per night
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House Cortona
250 m² house ∙ 6 guests ∙ 3 bedrooms

House Virgo

Cortona, Province of Arezzo, Italy
from £239
per night
from £239
per night
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Chalet Cortona
65 m² chalet ∙ 2 guests ∙ 1 bedroom

Chalet Aries

Cortona, Province of Arezzo, Italy
from £118
per night
from £118
per night
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House Cortona
365 m² house ∙ 14 guests ∙ 5 bedrooms

House Arcitenens

Cortona, Province of Arezzo, Italy
from £475
per night
from £475
per night
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House Passignano sul Trasimeno
200 m² house ∙ 6 guests ∙ 3 bedrooms

House Feronia

Passignano sul Trasimeno, Province of Perugia, Italy
from £862
per night
from £862
per night
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Farmhouse Cortona
110 m² farmhouse ∙ 6 guests ∙ 3 bedrooms

Farmhouse Cortona Sunshine

Cortona, Province of Arezzo, Italy
from £293
per night
4.9
Outstanding
(15 ratings)
from £293
per night
View deal
House Pievuccia
160 m² house ∙ 7 guests ∙ 2 bedrooms

House Santa Lucia

Pievuccia, Castiglion Fiorentino, Italy
from £133
per night
4.9
Outstanding
(54 ratings)
from £133
per night
View deal
House Castiglion Fiorentino
120 m² house ∙ 4 guests ∙ 2 bedrooms

House Volpe

Castiglion Fiorentino, Province of Arezzo, Italy
from £71
per night
5.0
Outstanding
(31 ratings)
from £71
per night
View deal
Chalet Passignano sul Trasimeno
70 m² chalet ∙ 2 guests ∙ 1 bedroom

Chalet Il Talamo

Passignano sul Trasimeno, Province of Perugia, Italy
from £168
per night
4.8
Outstanding
(40 ratings)
from £168
per night
View deal
Apartment Cortona
38 m² apartment ∙ 2 guests ∙ 1 bedroom

Apartment Antico Duomo

Cortona, Province of Arezzo, Italy
from £61
per night
from £61
per night
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Apartment Cortona
38 m² apartment ∙ 2 guests ∙ 1 bedroom

Apartment Antico Duomo

Cortona, Province of Arezzo, Italy
from £61
per night
from £61
per night
View deal
Apartment Cortona
45 m² apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Antico Duomo

Cortona, Province of Arezzo, Italy
from £78
per night
from £78
per night
View deal
Farmhouse Cortona
110 m² farmhouse ∙ 8 guests ∙ 4 bedrooms

Farmhouse La Coccinella

Cortona, Province of Arezzo, Italy
from £150
per night
5.0
Outstanding
(2 ratings)
from £150
per night
View deal
House Cortona
130 m² house ∙ 6 guests ∙ 3 bedrooms

House Bramasole

Cortona, Province of Arezzo, Italy
from £108
per night
4.6
Excellent
(32 ratings)
from £108
per night
View deal
Farmhouse Cortona
90 m² farmhouse ∙ 7 guests ∙ 4 bedrooms

Farmhouse La Dama

Cortona, Province of Arezzo, Italy
from £136
per night
4.8
Outstanding
(15 ratings)
from £136
per night
View deal
House Castiglion Fiorentino
200 m² house ∙ 6 guests ∙ 3 bedrooms

House La Felcaia

Castiglion Fiorentino, Province of Arezzo, Italy
from £108
per night
4.9
Outstanding
(44 ratings)
from £108
per night
View deal
Apartment Fossa del Lupo
120 m² apartment ∙ 6 guests ∙ 3 bedrooms

Apartment Rina

Fossa del Lupo, Cortona, Italy
from £76
per night
4.8
Outstanding
(5 ratings)
from £76
per night
View deal
House Castiglion Fiorentino
40 m² house ∙ 3 guests ∙ 1 bedroom

House Nido del Sorbino

Castiglion Fiorentino, Province of Arezzo, Italy
from £66
per night
4.8
Outstanding
(77 ratings)
from £66
per night
View deal

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Chalet Cortona
50 m² chalet ∙ 2 guests ∙ 1 bedroom

Chalet Amphora

Cortona, Province of Arezzo, Italy
from £102
per night
from £102
per night
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Customer reviews in Cortona

A country style house on a quiet farmstead with 2 other holiday homes, rural setting but a close drive to local amenities. Shady parking & shared pool area with sun loungers. Comfy beds though all decor is traditional & a little old fashioned. Fairly well stocked kitchen though there were no useful household items (soap, washing up liquid etc) & on arrival we found ants established in the kitchen. Also worth noting that EU plugs did not work so you need to buy Italian specific plugs

Jane

Reviewed on 25/08/2025

As we arrived along the Cypress Tree lined driveway we knew this was a special place. The views from the house are truly classic Tuscan rolling hills, with the house perched at the top of a gentle hill, the outlook heads down toward the bottom of the hill and then up toward Cortona. The infinity edge pool set in lovely gardens makes the most of this view. The house itself looks very much like the pictures with all rooms being very spacious. The loft room is particularly charming

DANIEL

Reviewed on 18/08/2025

A bit like the place you MUST visit one more time...that s the simple disription of the place that had ALL we wanted

JESPER

Reviewed on 21/07/2025

We had a very pleasant time at Lucija's house. The house is very clean and nicely decorated, and has enough space for six people, and everything necessary for a stay. All recommendations from me.

Jelena

Reviewed on 17/10/2024

Very nice big House in toscan style. Acctually two houses together with all facilities you need. Views are wunderfull and the big garden wel maintained. Had great evenings baking our own pizza's in the pizza oven with wooden fire together with a few bottles of wine.   M. as host living close by was always available to advise us about sightseeing oppertunities and service needed. We were with 8 and had a great time in this House.

Danny

Reviewed on 23/09/2024

We were a group of 5 families (9 adults, 10 children) who really loved our 1 week stay at the villa. The pool area is excellent and where we spent most of our time. Also made good use of the bikes provided for guest use, to explore the local area. Cortona town is an absolute must, very charming indeed - particularly at night. Villa is spacious and homely. Air con costs extra but we managed to just about get by without it in August, needed fans on at night though.

Matthew

Reviewed on 31/08/2022

2 lovely houses share 1 pool. Enjoyed the region (Cortona, Montepulciano, Siena) and the accomodation.

Nicolas

Reviewed on 05/08/2020

Pre-information was up-to-date and as expected, everything functioning. Friendly staff, clean house and nice environment around. Easy to access, good location for day trips. Nothing fancy but exceeding expectations and good value for money.

Jyrki

Reviewed on 23/09/2019

More travel options

Holiday houses and apartments in:

Discover Cortona

Discover the charm of a villa in Cortona, where your holiday home options are as diverse as they are delightful. Choose from apartments with kitchens and balconies, or indulge in a villa with a garden and pool. For a more rustic experience, consider a cozy country house. Many restored farmhouses in the region boast traditional Tuscan architecture and beautiful gardens, allowing you to enjoy the rural surroundings while remaining conveniently close to the city. A villa in Cortona offers the perfect blend of comfort and authenticity for your Tuscan getaway.

Cortona - Best Attractions

MAEC - Museum of the Etruscan Academy

MAEC - Museum of the Etruscan Academy

In the impressive Palazzo Casali from the 13th century, you immerse yourself in the ancient history of Italy at the MAEC - Museum of the Etruscan Academy. The modern museum in Cortona houses a collection of rare archaeological artifacts from the time of the Etruscans and Romans.

Hermitage Le Celle

Hermitage Le Celle

Saint Francis of Assisi founded the abbey in 1211 when he came to Cortona on a preaching journey. Years later, he is said to have written his famous testament here. Later, an oratory and a refectory were added to the complex.

Fortress Fortezza del Girifalco

Fortress Fortezza del Girifalco

Under the rule of the Medici, the Fortezza Medicea complex was expanded and consists of a total of four bastions and a main tower. The fortress can be visited, and there are changing exhibitions. The panoramic view of the Chiana Valley is particularly worthwhile.

Basilica of Santa Maria Nuova

Basilica of Santa Maria Nuova

The Renaissance church Santa Maria Nuova is one of the architectural treasures of Cortona. The house of worship was built in 1554 as an imposing central structure and was consecrated in 1610. Four large columns inside support the dome. From them, wing-like arms lead to smaller domes.

Republic Square

Republic Square

One of the most distinctive buildings in the Piazza della Repubblica in Cortona is the Palazzo Comunale from the 12th century. It testifies to the splendor of the Renaissance era and is known for its bell tower. Next to it rise other civic and town houses.

Cortona - In 3 days

Experience an unforgettable three-day vacation in one of the many high-quality villa in Cortona, a charming hill town in Tuscany. On your first day, explore the medieval atmosphere of Cortona and visit the Church of San Francesco with the impressive frescoes by Piero della Francesca. Stroll through Piazza della Repubblica and enjoy the view from the Fortezza del Girifalco. On the second day, you can visit the picturesque town of Arezzo, just 40 minutes from Cortona. Wander through the old town, enjoy Tuscan delicacies, and admire the historic buildings. The San Donato hill offers a magnificent view. End the day with a glass of Tuscan wine. On the third day, relaxation awaits you at the San Giovanni thermal baths in Rapolano Terme or a trip to Lake Trasimeno for water sports and recreation. The Valdichiana Outlet Village offers shopping opportunities, while wineries in the area are inviting for wine lovers. If time permits, a detour to Siena, one of the most beautiful cities in Tuscany, is worthwhile. Your vacation in Cortona promises culture, relaxation, and culinary delights amidst the beauty of Tuscany. Make your holiday unforgettable by relaxing in your villa in Cortona and exploring the region from there.

Cortona - Secret spots

The Pilgrimage Church of Santa Maria delle Grazie al Calcinaio
The Diocesan Museum in Cortona
Signorelli Square
Sodo Archaeological Park
Hand-picked and tested accommodation

Quality is our number one priority

Every property is checked before your arrival to ensure the best possible stay.

In-resort service and a 24/7 helpline

Make the most of our experience

Key collection is arranged by our helpful staff. Available 24/7 or on-site service to help you with all your questions, e.g.: tips and insights for your holiday destination and your booked accommodation.

A memorable holiday experience

Privacy and freedom in your own holiday homes

Be your own boss, eat whenever you want and make the most of plenty of space for all your friends and family.

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