Cortona Vacation Rentals

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Tonight
Dec 1 - Dec 2
Tomorrow
Dec 2 - Dec 3
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Cortona

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

Holiday home with panoramic terrace ideal for families and couples

Cortona
The price is ￥12,680
￥16,666 total
includes taxes & fees
Dec 2 - Dec 3
Holiday home with panoramic terrace ideal for families and couples
1 bedroom, iron/ironing board, free WiFi, bed sheets
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 ￥16,303
￥19,564 total
includes taxes & fees
Dec 2 - Dec 3
House in the Cortona countryside
1 bedroom, desk, iron/ironing board, WiFi
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 ￥17,118
￥20,922 total
includes taxes & fees
Dec 2 - Dec 3
Cortona Shabby Chic House<br>(Independent & balcony)
Exterior
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 ￥10,868
￥14,129 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Montecchio di Cortona
Property grounds
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 ￥18,114
￥33,874 total
includes taxes & fees
Dec 2 - Dec 3
La casa di Laura
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

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 ￥19,882
￥20,607 total
includes taxes & fees
Dec 2 - Dec 3
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
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

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 ￥16,937
￥17,662 total
includes taxes & fees
Dec 2 - Dec 3
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Terrace/patio
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34

Cortona
The price is ￥970,011
￥970,011 total
includes taxes & fees
Dec 2 - Dec 3
VILLA CORTONESE - Fifteen Bedroom Villa, Sleeps 34
Pool
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 ￥24,997
￥33,148 total
includes taxes & fees
Dec 2 - Dec 3
La Fonte, our quaint little west facing cottage for two people.
Exterior detail
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 ￥24,291
￥28,457 total
includes taxes & fees
Dec 8 - Dec 9
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

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 ￥35,533
￥43,067 total
includes taxes & fees
Dec 2 - Dec 3
Apartment 'Frantoio 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning
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

Cortona
The price is ￥41,662
￥51,625 total
includes taxes & fees
Dec 2 - Dec 3
A stylish Tuscan cottage for four people with stunning views over the valley and Cortona
Private kitchen
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 ￥13,014
￥16,763 total
includes taxes & fees
Dec 2 - Dec 3
Vacation home Beppina, typical cortonese house, in the center, animals welcome
Pool
EXCLUSIVE CASALE x38 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

EXCLUSIVE CASALE x38 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

Cortona
EXCLUSIVE CASALE x38 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona
A heated pool
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Cortona
The price is ￥56,128
￥63,662 total
includes taxes & fees
Dec 2 - Dec 3
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
Fridge, oven, stovetop, dishwasher
Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo

Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo

Cortona
The price is ￥113,088
￥113,994 total
includes taxes & fees
Dec 10 - Dec 11
Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo
Living area
APP. GLICINE x2 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

APP. GLICINE x2 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

Toscana
The price is ￥61,280
￥70,337 total
includes taxes & fees
Dec 4 - Dec 5
APP. GLICINE x2 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona
Interior
APP. ORTENSIA x3 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

APP. ORTENSIA x3 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

Toscana
The price is ￥64,885
￥74,848 total
includes taxes & fees
Dec 4 - Dec 5
APP. ORTENSIA x3 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona
Property grounds
APP. GERANIO x4 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

APP. GERANIO x4 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

Toscana
APP. GERANIO x4 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona
Dining
APP. MUGHETTO x4 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

APP. MUGHETTO x4 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona

Toscana
APP. MUGHETTO x4 Beautiful farmhouse surrounded by nature, with swimming pool just 3 km from Cortona
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

Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

10/10 Excellent
"Excellent staff and experiences! We had a wonderful time."
Sam 3-night trip
Posted 2 days ago
Il Falconiere - Relais e Chateaux

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?

Beautiful tuscan villa with pool, ideal for groups: Visitors give good reviews to this Cortona vacation home rental, which is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation. Some other top choices in Cortona are Il Rifugio, a farmhouse in Cortona with a panoramic view of Lake Trasimeno and Holiday home with panoramic terrace ideal for families and couples.

How many vacation rentals are there in Cortona?

With 156 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.