Cortona Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Cortona holiday rentals

Interior
La casa di Laura

Apartment in Cortona Old Town

La casa di Laura
10.0 out of 10, Exceptional, (1)
"Best sleep I’ve had in a long time. Very quiet area. Beautiful views. Absolutely gorgeous. Water and coffee were provided. Clean. Bruno was very patient with us with the language barrier. We also had trouble getting to the place because we were not getting service on our phone till we connected to WiFi. Bruno met us and showed us where to park after showing us the way to the apartment. Very steep climb up to the apartment from the parking area, but Cortona is overall steep. You will climb up...
United States
Angie F.
The price is HK$826
HK$1,596 total
includes taxes & fees
7 Jan - 8 Jan 2026
La casa di Laura
Dining
Montecchio di Cortona

Holiday Home in Montecchio

Montecchio di Cortona
9.0 out of 10, Wonderful, (2)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is HK$549
HK$714 total
includes taxes & fees
17 Jan - 18 Jan 2026
Montecchio di Cortona
Property grounds
City / Village Apartment in Cortona with 1 bedrooms sleeps 2

Apartment in Cortona Old Town

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
10.0 out of 10, Exceptional, (6)
"This place was such a great find! So central and easily reachable. We really enjoyed our stay!"
United States
Julie R.
The price is HK$856
HK$892 total
includes taxes & fees
6 Jan - 7 Jan 2026
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Interior
Cortona Shabby Chic House<br>(Independent & balcony)

Apartment in Cortona Old Town

Cortona Shabby Chic House<br>(Independent & balcony)
10.0 out of 10, Exceptional, (3)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is HK$865
HK$1,057 total
includes taxes & fees
26 Dec - 27 Dec
Cortona Shabby Chic House<br>(Independent & balcony)
Exterior
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

Holiday Home in Cortona

Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi
9.0 out of 10, Wonderful, (2)
"Pros: Il camino è stato come tornare bambini.Atmosfera Natalizia e tanto di più. Cons: Il Bidè non funzionava."
Italy
Anonymous traveller
The price is HK$982
HK$1,019 total
includes taxes & fees
6 Jan - 7 Jan 2026
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi
Exterior detail
Vacation home Beppina, typical cortonese house, in the center, animals welcome

Apartment in Cortona Old Town

Vacation home Beppina, typical cortonese house, in the center, animals welcome
The price is HK$648
HK$835 total
includes taxes & fees
29 Dec - 30 Dec
Vacation home Beppina, typical cortonese house, in the center, animals welcome
Property grounds
Cortonas Rooftop Nest

Apartment in Cortona Old Town

Cortonas Rooftop Nest
10.0 out of 10, Exceptional, (11)
"Absolute gem of a property. Margherita is an excellent host as well!"
United States
Robin F.
The price is HK$1,310
HK$1,502 total
includes taxes & fees
6 Jan - 7 Jan 2026
Cortonas Rooftop Nest
Pool
Apartment "Papà Giuseppe La Colombaia" with Shared Pool & Wi-Fi

Holiday Home in Cortona

Apartment "Papà Giuseppe La Colombaia" with Shared Pool & Wi-Fi
10.0 out of 10, Exceptional, (1)
"Pros: Es war ganz toll. Das Klima mit 34 Grad sehr heiß aber durch den Pool geht auch das sehr gut. Der Gastgeber ist super freundlich... wir sprechen null italienisch aber das war nur ein kleines Hinderniss."
Germany
Anonymous traveller
The price is HK$1,231
HK$1,267 total
includes taxes & fees
8 Jan - 9 Jan 2026
Apartment "Papà Giuseppe La Colombaia" with Shared Pool & Wi-Fi
Exterior
Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy

Villa in Cortona

Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
10.0 out of 10, Exceptional, (27)
"Great location with gorgeous views over the Chiana hills, and nearby restaurants. We enjoyed discovering Cortona and several hill towns in the ares"
United States
Patricia H.
The price is HK$2,620
HK$2,987 total
includes taxes & fees
31 Dec - 1 Jan 2026
Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Exterior
Apartment 'Frantoio 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning

Apartment in Cortona

Apartment 'Frantoio 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning
10.0 out of 10, Exceptional, (1)
"Pros: Abbiamo soggiornato a Borgo Syrah per 3 notti. Soggiorno stupendo. Location meravigliosa, immersa nella natura. Un'oasi di pace"
Italy
Anonymous traveller
The price is HK$2,117
HK$2,499 total
includes taxes & fees
24 Jan - 25 Jan 2026
Apartment 'Frantoio 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning
Terrace/patio
A stylish Tuscan cottage for four people with stunning views over the valley and Cortona

Cottage in Cortona

A stylish Tuscan cottage for four people with stunning views over the valley and Cortona
The price is HK$2,105
HK$2,563 total
includes taxes & fees
6 Jan - 7 Jan 2026
A stylish Tuscan cottage for four people with stunning views over the valley and Cortona
1 bedroom, iron/ironing board, free WiFi, bed sheets
House in the Cortona countryside

Holiday Home in Fratticciola

House in the Cortona countryside
10.0 out of 10, Exceptional, (1)
"Host was extremely welcoming. Met us when we arrived and explained usage of all the amenities, including the clothes washer. Cottage was quintessential Rural Italian home. The hostess even provided us with some local wine and homemade biscotti. "
United States
Nancy F.
The price is HK$824
HK$989 total
includes taxes & fees
25 Dec - 26 Dec
House in the Cortona countryside
Terrace/patio
La Fonte, our quaint little west facing cottage for two people.

Cottage in Cortona

La Fonte, our quaint little west facing cottage for two people.
The price is HK$1,263
HK$1,675 total
includes taxes & fees
31 Dec - 1 Jan 2026
La Fonte, our quaint little west facing cottage for two people.
Property grounds
Nice apartment for 2 people with WIFI and pets allowed

Apartment in Cortona Old Town

Nice apartment for 2 people with WIFI and pets allowed
10.0 out of 10, Exceptional, (1)
The price is HK$938
HK$974 total
includes taxes & fees
6 Jan - 7 Jan 2026
Nice apartment for 2 people with WIFI and pets allowed
Exterior
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Villa in Cortona

Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
The price is HK$2,827
HK$3,208 total
includes taxes & fees
8 Jan - 9 Jan 2026
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
Exterior
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Holiday Home in Cortona

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
8.0 out of 10, Very good, (1)
"Pros: Authentiek Toscaanse boerderij ( wij hadden de bovenste etage) met prachtige tuin en lekker zwembad met mooi uitzicht. De gastheer Angelo was top en de Toscaanse diners waren onvergetelijk. Bedankt dat ik mijn verjaardag zo heb mogen vieren. Hele mooie herinnering. Pizza’s bakken was ook een feest. Ook heel fijn dat er een airco was. Onze 4 puber jongens hebben zich prima vermaakt en leuk dat er nog andere gasten zijn uit andere appartementen die je dan ziet op hetToscaanse diner. Top...
Netherlands
Anonymous traveller
The price is HK$1,005
HK$1,041 total
includes taxes & fees
1 Jan - 2 Jan 2026
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Pool
Family Apartment in the heart of Tuscany with swimming pool (Da Vinci)

Apartment in cortona

Family Apartment in the heart of Tuscany with swimming pool (Da Vinci)
The price is HK$4,587
HK$5,248 total
includes taxes & fees
1 Jan - 2 Jan 2026
Family Apartment in the heart of Tuscany with swimming pool (Da Vinci)
Pool
Apartment "Papà Giuseppe La Cantina" with Shared Pool & Wi-Fi

Holiday Home in Cortona

Apartment "Papà Giuseppe La Cantina" with Shared Pool & Wi-Fi
8.0 out of 10, Very good, (1)
"Pros: Heel leuk is de maandagavond met alle gasten gezamenlijk eten op uitnodiging van de gastheer. Cons: In de advertentie wordt airco aangegeven maar die is er niet,"
United States
Anonymous traveller
The price is HK$726
HK$762 total
includes taxes & fees
5 Jan - 6 Jan 2026
Apartment "Papà Giuseppe La Cantina" with Shared Pool & Wi-Fi
Exterior
Apartment "La Vecchia Fornace Casa Gialla" with Shared Pool & Wi-Fi

Holiday Home in Cortona

Apartment "La Vecchia Fornace Casa Gialla" with Shared Pool & Wi-Fi
The price is HK$921
HK$958 total
includes taxes & fees
17 Jan - 18 Jan 2026
Apartment "La Vecchia Fornace Casa Gialla" with Shared Pool & Wi-Fi
Exterior
Holiday Home 'Magazzino 1' with Shared Pool, Wi-Fi and Air Conditioning

Apartment in Cortona

Holiday Home 'Magazzino 1' with Shared Pool, Wi-Fi and Air Conditioning
10.0 out of 10, Exceptional, (1)
"Pros: La casa super spaziosa e pulita. Beatrice ci ha accolto subito e ci ha fatto sentire a casa. Esperienza da rifare assolutamente compresa la degustazione in struttura con i loro vini locali e visita in cantina, devo dire che ad aggiungere un plus sono stati i prodotti fatti in casa (focacce, pappa al pomodoro e molto altro) da affiancare ai calici. Cons: Peccato per la piscina e spa chiuse ma torneremo per testare sicuramente questo servizi"
Italy
Anonymous traveller
The price is HK$2,796
HK$3,178 total
includes taxes & fees
7 Jan - 8 Jan 2026
Holiday Home 'Magazzino 1' with Shared Pool, Wi-Fi and Air Conditioning
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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Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 6 days ago
Monastero di Cortona Hotel & Spa

Find out more about Cortona

Search for holiday rentals in Cortona on Expedia! You can easily find your home rentals, villas, holiday apartments in Cortona using one of the methods below:

  • View our selection of featured holiday rentals in Cortona
  • Use the map to find apartments and other holiday homes in the Cortona neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cortona while they last

Look no further and take a look at our great range of rental properties in Cortona!

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.

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

Il Rifugio, a farmhouse in Cortona with a panoramic view of Lake Trasimeno : This highly rated holiday home rental in Cortona is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Some other top choices in Cortona are beautiful tuscan villa with pool, ideal for groups and Casa Fontelunga, Tuscan holiday villa with private pool.

How many holiday rentals are there in Cortona?

With 144 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 Signorelli Theatre and Museum of the Etruscan Academy, whereas Val di Chiana is one spot to enjoy nature. While here, Piazza della Repubblica and Giuseppe Garibaldi Memorial 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.