Cortona Vacation Rentals

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Cortona vacation rentals

Property grounds
Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥12,857
￥16,898 total
includes taxes & fees
Dec 29 - Dec 30
Holiday home with panoramic terrace ideal for families and couples
1 bedroom, desk, iron/ironing board, WiFi
Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is ￥17,357
￥21,214 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cortona Shabby Chic House<br>(Independent & balcony)
Exterior
Montecchio di Cortona

Montecchio di Cortona

Montecchio di Cortona
Montecchio
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 ￥11,020
￥14,326 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Montecchio di Cortona
1 bedroom, iron/ironing board, free WiFi, bed sheets
House in the Cortona countryside

House in the Cortona countryside

House in the Cortona countryside
Fratticciola
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 ￥16,531
￥19,837 total
includes taxes & fees
Dec 29 - Dec 30
House in the Cortona countryside
Property grounds
La casa di Laura

La casa di Laura

La casa di Laura
Cortona Old Town
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 ￥16,531
￥31,960 total
includes taxes & fees
Jan 7 - Jan 8, 2026
La casa di Laura
1 bedroom, travel crib, free WiFi
City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
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 ￥17,174
￥17,909 total
includes taxes & fees
Jan 8 - Jan 9, 2026
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Fridge, oven, stovetop, dishwasher
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
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 traveler
The price is ￥20,193
￥20,929 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Fridge, oven, stovetop, dishwasher
Apartment "Papà Giuseppe La Cantina" with Shared Pool & Wi-Fi

Apartment "Papà Giuseppe La Cantina" with Shared Pool & Wi-Fi

Apartment "Papà Giuseppe La Cantina" with Shared Pool & Wi-Fi
Cortona
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 traveler
The price is ￥13,127
￥13,863 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Apartment "Papà Giuseppe La Cantina" with Shared Pool & Wi-Fi
TV
Netik Apartment Cortona- Garden & Vineyard in Tuscany

Netik Apartment Cortona- Garden & Vineyard in Tuscany

Netik Apartment Cortona- Garden & Vineyard in Tuscany
Vallone Pip
The price is ￥11,939
￥20,572 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Netik Apartment Cortona- Garden & Vineyard in Tuscany
Interior
Elegant cottage for two people

Elegant cottage for two people

Elegant cottage for two people
cortona
The price is ￥33,796
￥42,061 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Elegant cottage for two people
Private kitchen
Vacation home Beppina, typical cortonese house, in the center, animals welcome

Vacation home Beppina, typical cortonese house, in the center, animals welcome

Vacation home Beppina, typical cortonese house, in the center, animals welcome
Cortona Old Town
The price is ￥13,011
￥16,759 total
includes taxes & fees
Dec 29 - Dec 30
Vacation home Beppina, typical cortonese house, in the center, animals welcome
Pool
La Fonte, our quaint little west facing cottage for two people.

La Fonte, our quaint little west facing cottage for two people.

La Fonte, our quaint little west facing cottage for two people.
Cortona
The price is ￥25,347
￥33,612 total
includes taxes & fees
Dec 29 - Dec 30
La Fonte, our quaint little west facing cottage for two people.
Pool
A stylish Tuscan cottage for four people with stunning views over the valley and Cortona

A stylish Tuscan cottage for four people with stunning views over the valley and Cortona

A stylish Tuscan cottage for four people with stunning views over the valley and Cortona
Cortona
The price is ￥42,245
￥52,347 total
includes taxes & fees
Dec 29 - Dec 30
A stylish Tuscan cottage for four people with stunning views over the valley and Cortona
Outdoor dining
Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy

Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy

Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Cortona
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 ￥52,722
￥60,103 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Exterior detail
Cortonas Rooftop Nest

Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
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 ￥26,327
￥30,375 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cortonas Rooftop Nest
A heated pool
Apartment 'Frantoio 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning

Apartment 'Frantoio 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning

Apartment 'Frantoio 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
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 traveler
The price is ￥36,030
￥43,669 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Apartment 'Frantoio 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning
Dining
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1)
"Pros: il luogo che ci circondava rilassante ottimo. Cons: nulla come dicevo luogo ottimo."
Italy
Anonymous traveler
The price is ￥127,887
￥135,539 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Pool
Family Apartment in the heart of Tuscany with swimming pool (Da Vinci)

Family Apartment in the heart of Tuscany with swimming pool (Da Vinci)

Family Apartment in the heart of Tuscany with swimming pool (Da Vinci)
cortona
The price is ￥91,837
￥105,613 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Family Apartment in the heart of Tuscany with swimming pool (Da Vinci)
TV, fireplace
Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
The price is ￥83,774
￥91,413 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning
Dining
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi
Cortona
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 traveler
The price is ￥19,712
￥20,447 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi
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 8 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 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?

Il Rifugio, a farmhouse in Cortona with a panoramic view of Lake Trasimeno : Visitors give good reviews to this Cortona vacation home rental, which is located in the mountains and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 vacation rentals are there in Cortona?

With 144 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?

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 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.