Cortona Vacation Rentals from CA $316: Short-Term Rentals for 2026

Q: 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. Another good choice for your trip to Cortona is Casa Bacco - private house with a remarkable garden in the centre of Cortona .

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Our top choices for Cortona vacation rentals

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

1. B&B Piccolo Hotel

Cortona Old Town

mansoor

CA $248 total

includes taxes & fees

Sep 24 - Sep 25

A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

2. CASA AMBRA

Cortona Old Town

CA $222 total

includes taxes & fees

Sep 19 - Sep 20

A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

3. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

CA $159 total

includes taxes & fees

Sep 14 - Sep 15

4. Vicolo Della Scala Rooms - Il Sole

Cortona Old Town

CA $170 total

includes taxes & fees

Sep 21 - Sep 22

A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

5. San Michele al Borgo

Castiglion Fiorentino

Vern

CA $208 total

includes taxes & fees

Sep 13 - Sep 14

An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

6. Fontelunga Hotel & Villas

Foiano della Chiana

Shelby

CA $501 total

includes taxes & fees

Sep 19 - Sep 20

7. iConic Wellness Resort

Arezzo

Rheymarie

CA $143 total

includes taxes & fees

Oct 11 - Oct 12

A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

8. Castello di Gargonza

Monte San Savino

Ariel

CA $361 total

includes taxes & fees

Oct 12 - Oct 13

A crowded restaurant with brick walls and multiple tables and chairs.

9. La Locanda di San Francesco

Montepulciano

Isabelle

CA $335 total

includes taxes & fees

Oct 8 - Oct 9

10. Casale dell'Assiolo

Castiglione del Lago

CA $192 total

includes taxes & fees

Sep 13 - Sep 14

A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

11. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

CA $131 total

includes taxes & fees

Oct 12 - Oct 13

An interior courtyard with stone columns, arches, and a mosaic.

12. Meublé Il Riccio

Montepulciano

Marlenne

CA $243 total

includes taxes & fees

Oct 12 - Oct 13

A historic building with a tower, a courtyard, and a well-lit entrance.

13. Abbadia Sicille Relais

Trequanda

Robert

CA $210 total

includes taxes & fees

Oct 12 - Oct 13

A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

14. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

CA $210 total

includes taxes & fees

Sep 30 - Oct 1

A spa area with a stone-walled arch, a hot tub, and a small window.

15. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

CA $177 total

includes taxes & fees

Oct 12 - Oct 13

An arched doorway leading to a building with a wooden door and a staircase.

16. Residenza Fabroni

Montepulciano

Nicholas

CA $149 total

includes taxes & fees

Sep 13 - Sep 14

A terrace with a table set for breakfast, overlooking a scenic landscape.

17. Delcorto Suites

Montepulciano

Denise

CA $306 total

includes taxes & fees

Oct 6 - Oct 7

A patio area with outdoor seating, potted plants, and a view of the landscape.

18. Affitacamere Maria Gabriella

Pienza

Young Rok

CA $211 total

includes taxes & fees

Oct 4 - Oct 5

A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

19. Villa Fontis Rapolano

Rapolano Terme

Barbara

CA $142 total

includes taxes & fees

Oct 11 - Oct 12

A courtyard with a pool, stone benches, and a view of a hill.

20. TH Perugia - Castello di Monterone

Perugia

Baudouin

CA $319 total

includes taxes & fees

Sep 29 - Sep 30

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Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Excelent"

Il Falconiere - Relais e Chateaux

10/10 Excellent

"Il Falconiere treats you as a true guest. Welcoming, courteous and professional were all staff members. Food truly excellent and with the Michelin star, you will enjoy a sumptuous meal, ample portions, amuse bouche at meal's start with a surprise dessert tray with little bites. All staff you interact with are well trained and genuinely friendly and still professional. Our room was in the origjnal residence and had a modern bathroom, lovely size bedroom, anti room with a second desk. In the salon, upon entering the suite, you will find "gifts" left for guests with seating if wishing to entertain. Our group, 4 persons, were very impressed with accommodations, meals and courteous staff. Of course, owner and chef, Silvia Baracchi, too was gracious coming to tables in the evening, welcoming guests and if passed anyone during day, always smiled a buon giorno to one and all. A delightful experience and wonderful to share with good friends."

A small cottage in authentic Tuscany. Serves 4

10/10 Excellent

"We had a wonderful time during our holiday at Casina del Bibo! Anna Maria and Lorella gave us a warm welcome, they surprised us with wine, fresh fruits and lots of local products. The appartment was very clean and comfortable, the airconditioning worked perfectly and there were mosquito screens installed in most of the windows. The location of the appartment is ideal. We went to a lot of different cities like Arezzo, Siena, Montepulciano and Perugia during our stay of 14 days. The town of Cortona, which is 15 minutes by car, was very nice to visit for a few times. The appartment is in an a quiet village, but many facilities like a supermarket and restaurants are close by. Our stay at Casina del Bibo surpassed our expectations and we would recommend it to anyone who wants a comfortable quiet place to enjoy their holiday, but who also likes to explore the surrounding towns and countryside."

Cortona Resort - Le Terre Dei Cavalieri

10/10 Excellent

"Beautiful, peaceful resort with helpful staff. Delicious, plentiful breakfast buffet on outside patio included with stay. If A/C is a deal-breaker for you, be aware that it was not very powerful (which is common in Italy, we’ve found) and we thought the room was quite warm and muggy during the summer. However, the staff was very helpful and provided us with a fan that helped a bit. Overall I highly recommend this property."

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cortona vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cortona vacation rentals we have selected for you start as low as CA $316 per night. Entering your travel dates in the search wizard 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.

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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. Another good choice for your trip to Cortona is Casa Bacco - private house with a remarkable garden in the centre of Cortona.

How many vacation rentals are there in Cortona?

With 166 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.

Cortona Vacation Rentals

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Check prices for these dates

Our top choices for Cortona vacation rentals

1. B&B Piccolo Hotel

2. CASA AMBRA

3. Vicolo Della Scala Rooms - La Luna

4. Vicolo Della Scala Rooms - Il Sole

5. San Michele al Borgo

6. Fontelunga Hotel & Villas

7. iConic Wellness Resort

8. Castello di Gargonza

9. La Locanda di San Francesco

10. Casale dell'Assiolo

11. Artisti del Cavallo Tourism

12. Meublé Il Riccio

13. Abbadia Sicille Relais

14. Bed & Breakfast Vicolo dell'Oste

15. DormiVeglia B&B

16. Residenza Fabroni

17. Delcorto Suites

18. Affitacamere Maria Gabriella

19. Villa Fontis Rapolano

20. TH Perugia - Castello di Monterone

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Find out more about Cortona

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