Cortona Vacation Rentals

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Our top choices for Cortona vacation rentals

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.6 out of 10, Exceptional, (21 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$128 nightly
The price is $145
May 18 - May 19
Total with taxes and fees
B&B Piccolo Hotel

CASA AMBRA

CASA AMBRA
Cortona Old Town
$232 nightly
The price is $258
May 9 - May 10
Total with taxes and fees
CASA AMBRA

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$103 nightly
The price is $117
May 5 - May 6
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
$109 nightly
The price is $124
May 15 - May 16
Total with taxes and fees
Vicolo Della Scala Rooms - Il Sole

Il Rifugio del Borgo

Il Rifugio del Borgo
Città della Pieve
$127 nightly
The price is $142
May 9 - May 10
Total with taxes and fees
Il Rifugio del Borgo

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (36 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
$91 nightly
The price is $107
May 5 - May 6
Total with taxes and fees
iConic Wellness Resort

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (130 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
$133 nightly
The price is $151
May 11 - May 12
Total with taxes and fees
Bed & Breakfast Vicolo dell'Oste

Castello di Monterone

Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (309 reviews)
"Beautiful hotel in restored castle. Staff were kind and welcoming. "
United Kingdom
Stuart
$201 nightly
The price is $229
May 4 - May 5
Total with taxes and fees
Castello di Monterone

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (173 reviews)
"The room was really clean and as described. Unfortunately, the hotel restaurant was closed and that was not mentioned on the site. I learned about it the day before my arrival. Fortunately, the host had good restaurant suggestions. The hotel advertise a pool and a jacuzzi, they have both but the pool was VERY cold (normal in April) and the jacuzzi was not inviting (bee nest, Luke warm, in the shade...). Concerning the breakfast, note that it is not a buffet, a box get delivered to your room. You...
Canada
Chantal
$182 nightly
The price is $204
Jun 3 - Jun 4
Total with taxes and fees
Abbadia Sicille Relais

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (140 reviews)
"A wonderful hotel - great location, friendly staff, comfortable rooms. "
United States
beverly
$228 nightly
The price is $258
May 6 - May 7
Total with taxes and fees
Hotel San Gregorio

Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (37 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
$111 nightly
The price is $127
May 4 - May 5
Total with taxes and fees
Residence al Lago

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (137 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
$216 nightly
The price is $242
May 10 - May 11
Total with taxes and fees
La Locanda di San Francesco

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (93 reviews)
"Nothing negative could be said about this absolutely fabulous property. Great staff, great location, best room of our 22 day, 11 stop trip. Easy luggage so off, great everything. We will be back and will definitely stay here again. "
United States
Michael
$164 nightly
The price is $185
May 17 - May 18
Total with taxes and fees
Meublé Il Riccio

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$95 nightly
The price is $109
May 5 - May 6
Total with taxes and fees
DormiVeglia B&B

Residenza d'epoca Ca' de Principi

Residenza d'epoca Ca' de Principi
Piegaro
9.8 out of 10, Exceptional, (13 reviews)
"The hotel was charming, and the staff really nice. Breakfast had lots of options. The room was large and beautiful view of the hills. The bed was comfortable."
United States
Robyn
$139 nightly
The price is $152
May 20 - May 21
Total with taxes and fees
Residenza d'epoca Ca' de Principi

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (181 reviews)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
$89 nightly
The price is $105
Jun 3 - Jun 4
Total with taxes and fees
Cameracaffè Centro

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (47 reviews)
"Our stay was great. "
United States
Elena
$128 nightly
The price is $146
May 5 - May 6
Total with taxes and fees
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (99 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
$87 nightly
The price is $100
May 12 - May 13
Total with taxes and fees
Residenza Fabroni

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
$64 nightly
The price is $71
May 19 - May 20
Total with taxes and fees
L'Antica Sosta

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
$200 nightly
The price is $224
May 10 - May 11
Total with taxes and fees
Delcorto Suites
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

Find out more about Cortona

Everything you need to know about Cortona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cortona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cortona vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cortona vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cortona. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cortona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $146 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cortona rentals

At Expedia, we put the best Cortona vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cortona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cortona vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cortona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Podere Casorbica with free parking, large garden, private pool.: Visitors give good reviews to this Cortona vacation home rental, which is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 balcony and a garden. Some other top choices in Cortona are Casa Bacco - private house with a remarkable garden in the centre of Cortona and beautiful tuscan villa with pool, ideal for groups.

How many vacation rentals are there in Cortona?

With 143 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.