Cortona Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Cortona vacation rentals

Lobby

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 P7,693
P8,745 total
includes taxes & fees
May 18 - May 19
B&B Piccolo Hotel
Front of property

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is P6,310
P7,224 total
includes taxes & fees
Apr 22 - Apr 23
Vicolo Della Scala Rooms - La Luna
Room

CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is P10,991
P12,302 total
includes taxes & fees
Apr 18 - Apr 19
CASA AMBRA
Front of property

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is P7,053
P8,041 total
includes taxes & fees
Apr 20 - Apr 21
Vicolo Della Scala Rooms - Il Sole
Exterior detail

Il Rifugio del Borgo

Il Rifugio del Borgo
Città della Pieve
The price is P6,941
P7,777 total
includes taxes & fees
Apr 19 - Apr 20
Il Rifugio del Borgo
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

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 P5,340
P6,299 total
includes taxes & fees
May 4 - May 5
iConic Wellness Resort
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (91 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
The price is P10,075
P11,365 total
includes taxes & fees
Apr 18 - Apr 19
Meublé Il Riccio
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (172 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is P9,140
P10,266 total
includes taxes & fees
Apr 26 - Apr 27
Abbadia Sicille Relais
Outdoor pool, sun loungers

Castello di Monterone

Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (307 reviews)
"Beautiful hotel in restored castle. Staff were kind and welcoming. "
United Kingdom
Stuart
The price is P11,569
P13,221 total
includes taxes & fees
Apr 23 - Apr 24
Castello di Monterone
Exterior

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 P6,187
P7,088 total
includes taxes & fees
Apr 19 - Apr 20
Bed & Breakfast Vicolo dell'Oste
Exterior

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (53 reviews)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
The price is P7,144
P9,619 total
includes taxes & fees
Apr 19 - Apr 20
Affitacamere Maria Gabriella
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (134 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
The price is P9,898
P11,170 total
includes taxes & fees
Apr 28 - Apr 29
La Locanda di San Francesco
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (79 reviews)
"Fantastic place"
United States
Clifford
The price is P11,105
P12,499 total
includes taxes & fees
May 10 - May 11
Casanova - Panoramic Rooms and Suites
Porch

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 P6,620
P7,706 total
includes taxes & fees
May 17 - May 18
Cameracaffè Centro
Food and drink

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 P12,828
P14,534 total
includes taxes & fees
May 7 - May 8
Hotel San Gregorio
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (98 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is P4,975
P5,755 total
includes taxes & fees
Apr 20 - Apr 21
Residenza Fabroni
Exterior

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is P3,894
P4,284 total
includes taxes & fees
Apr 21 - Apr 22
L'Antica Sosta
Front of property

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 P5,678
P6,529 total
includes taxes & fees
Apr 29 - Apr 30
Residence al Lago
Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is P10,812
P12,177 total
includes taxes & fees
Apr 19 - Apr 20
Delcorto Suites
Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (10 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
The price is P7,510
P8,403 total
includes taxes & fees
Apr 18 - Apr 19
La Piccola Locanda
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cortona Hotel Reviews

Locanda agli Amici

Locanda agli Amici

10/10 Excellent
"The manager of this establishment, Silvie, was wonderful. We missed the turn to get to the property & she offered to come find us. This is an experience I never received in all my travels. She went above & beyond to accommodate us. "
Evangeliste 2-night trip
Posted 2 days ago
Locanda agli Amici

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.

How many vacation rentals are there in Cortona?

With 149 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 Museum of the Etruscan Academy and Signorelli Theatre, 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.