A hillside town with historic buildings, a church, and vineyards.

Cortona Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Cortona vacation rentals

Lobby

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (23 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is P8,049
P9,137 total
includes taxes & fees
Jul 20 - Jul 21
B&B Piccolo Hotel
Soundproofing, iron/ironing board, WiFi (free)

CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is P8,655
P9,732 total
includes taxes & fees
Aug 3 - Aug 4
CASA AMBRA
Front of property

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is P7,035
P8,021 total
includes taxes & fees
Jul 20 - Jul 21
Vicolo Della Scala Rooms - Il Sole
Front of property

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is P6,295
P7,206 total
includes taxes & fees
Jul 20 - Jul 21
Vicolo Della Scala Rooms - La Luna
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, (38 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is P9,175
P10,516 total
includes taxes & fees
Jul 19 - Jul 20
iConic Wellness Resort
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (139 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is P6,967
P7,946 total
includes taxes & fees
Jul 20 - Jul 21
Bed & Breakfast Vicolo dell'Oste
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (114 reviews)
"It was very well located ."
Canada
Marlenne
The price is P10,050
P11,337 total
includes taxes & fees
Jul 24 - Jul 25
Meublé Il Riccio
Outdoor pool, sun loungers

TH Perugia - Castello di Monterone

TH Perugia - Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (316 reviews)
"Breakfast buffet was outstanding."
United States
Larraine
The price is P12,464
P14,204 total
includes taxes & fees
Jul 30 - Jul 31
TH Perugia - Castello di Monterone
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is P13,152
P14,678 total
includes taxes & fees
Jul 19 - Jul 20
Abbadia Sicille Relais
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (103 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is P5,539
P6,375 total
includes taxes & fees
Jul 22 - Jul 23
Residenza Fabroni
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (145 reviews)
"Great location."
United States
James
The price is P10,322
P11,636 total
includes taxes & fees
Jul 22 - Jul 23
La Locanda di San Francesco
BBQ/picnic area

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 P8,335
P9,168 total
includes taxes & fees
Jul 18 - Jul 19
Residenza d'epoca Ca' de Principi
Couples treatment rooms, sauna, hot tub, steam room, body treatments

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, (48 reviews)
"Our stay was great. "
United States
Elena
The price is P6,751
P7,708 total
includes taxes & fees
Jul 20 - Jul 21
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (11 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 P7,492
P8,382 total
includes taxes & fees
Jul 19 - Jul 20
La Piccola Locanda
Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (38 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is P10,750
P12,107 total
includes taxes & fees
Jul 18 - Jul 19
Delcorto Suites
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (151 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is P14,274
P16,125 total
includes taxes & fees
Jul 24 - Jul 25
Hotel San Gregorio
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, (92 reviews)
"Our stay at Casanova Panoramic Rooms was absolutely wonderful. The room was beautiful, spotless, and the view was simply breathtaking. The entire check-in process was smooth and welcoming, and having convenient parking made everything even easier. We also loved the restaurant—the food was delicious, and breakfast was excellent. Every part of our stay exceeded our expectations. We would definitely stay here again and highly recommend it to anyone visiting the area."
United States
Anonymous traveler
The price is P11,078
P12,468 total
includes taxes & fees
Jul 22 - Jul 23
Casanova - Panoramic Rooms and Suites
Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is P6,537
P7,472 total
includes taxes & fees
Aug 17 - Aug 18
DormiVeglia B&B
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (189 reviews)
"This property met all our needs for a one night stay. It is conveniently located near the train station and near the old town area. The people we encountered were friendly and helpful. The breakfast choices were plentiful and the breakfast area on the rooftop patio was beautiful. The only negative was that the walks of the room were thin and we could hear neighbors quite a bit. "
United States
Roger
The price is P5,578
P6,559 total
includes taxes & fees
Jul 24 - Jul 25
Cameracaffè Centro
Front of property

RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.6 out of 10, Exceptional, (7 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is P5,453
P6,351 total
includes taxes & fees
Jul 22 - Jul 23
RESIDENCE LECCIO
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

Relais Villa Baldelli

Relais Villa Baldelli

10/10 Excellent
"Great hotel! It’s a very nice villa feel like. Would recommend renting a car, as taxis are expensive and hard to book. Also I wish they served lunch or dinner on site."
Nicoly 5-night trip
Posted 1 day ago
Relais Villa Baldelli

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:

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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 153 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 Santa Maria Nuova 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.