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
The price is CA $173
CA $197 total
includes taxes & fees
May 18 - May 19
B&B Piccolo Hotel

CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is CA $362
CA $403 total
includes taxes & fees
May 4 - May 5
CASA AMBRA

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is CA $139
CA $160 total
includes taxes & fees
May 4 - May 5
Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is CA $149
CA $171 total
includes taxes & fees
May 4 - May 5
Vicolo Della Scala Rooms - Il Sole

Il Rifugio del Borgo

Il Rifugio del Borgo
Città della Pieve
The price is CA $172
CA $193 total
includes taxes & fees
May 9 - May 10
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
The price is CA $134
CA $157 total
includes taxes & fees
May 4 - May 5
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
The price is CA $186
CA $211 total
includes taxes & fees
May 18 - May 19
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
The price is CA $281
CA $321 total
includes taxes & fees
May 18 - May 19
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
The price is CA $247
CA $277 total
includes taxes & fees
Jun 3 - Jun 4
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
The price is CA $314
CA $355 total
includes taxes & fees
May 10 - May 11
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
The price is CA $145
CA $166 total
includes taxes & fees
May 15 - May 16
Residence al Lago

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (136 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
The price is CA $293
CA $329 total
includes taxes & fees
May 10 - May 11
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
The price is CA $222
CA $251 total
includes taxes & fees
May 17 - May 18
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
The price is CA $131
CA $150 total
includes taxes & fees
May 4 - May 5
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
The price is CA $188
CA $207 total
includes taxes & fees
May 20 - May 21
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
The price is CA $121
CA $143 total
includes taxes & fees
Jun 3 - Jun 4
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
The price is CA $192
CA $217 total
includes taxes & fees
May 5 - May 6
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
The price is CA $128
CA $148 total
includes taxes & fees
May 12 - May 13
Residenza Fabroni

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is CA $88
CA $97 total
includes taxes & fees
Jun 3 - Jun 4
L'Antica Sosta

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is CA $271
CA $305 total
includes taxes & fees
May 10 - May 11
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cortona. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.