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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Portole holiday rentals

A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

1. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
9.8 out of 10, Exceptional, (9 reviews)
"Nice property"
United States
Joseph
The price is £81
includes taxes & fees
11 Nov - 12 Nov
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Pool

2. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (45 reviews)
"It was wonderful!"
United States
Wade
The price is £66
includes taxes & fees
11 Nov - 12 Nov
iConic Wellness Resort
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

3. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is £170
includes taxes & fees
11 Nov - 12 Nov
CASA AMBRA
A view from a window overlooking a courtyard with stone buildings and a tower.

4. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (39 reviews)
"we loved the rooms—especially"
United States
Jean V. A.
The price is £151
includes taxes & fees
9 Dec - 10 Dec
La Finestra sul Teatro
A couple relaxing in a spa setting with a visible logo on the wall, a reception desk, and a plant in the background.

5. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is £113
includes taxes & fees
12 Nov - 13 Nov
San Michele al Borgo
A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

6. Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
10.0 out of 10, Exceptional, (12 reviews)
"Absolute gem of a property. Margherita is an excellent host as well!"
United States
Robin F.
The price is £125
includes taxes & fees
11 Nov - 12 Nov
Cortonas Rooftop Nest
A staircase with two lit lanterns on the wall.

7. Cortona Shabby Chic House<br>(Independent & Balcony)

Cortona Shabby Chic House<br>(Independent & Balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3 reviews)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is £117
includes taxes & fees
20 Nov - 21 Nov
Cortona Shabby Chic House<br>(Independent & Balcony)
A modern apartment with a kitchen, dining area, living room, and a balcony.

8. Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning

Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning
Tuoro sul Trasimeno
10.0 out of 10, Exceptional, (1 review)
"Pros: Hervorragende Ausstattung der Küche. Sehr gute Kommunikation mit dem Gastgeber. Sehr sauber und liebevoll eingerichtet."
Germany
Anonymous traveller
The price is £161
includes taxes & fees
11 Nov - 12 Nov
Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning
A black dog sitting on stone steps in front of a brown double door with a metal decorative archway.

9. Beppina Vacation Home, a traditional Cortona-style house, in the center, pets welcome

Beppina Vacation Home, a traditional Cortona-style house, in the center, pets welcome
Cortona Old Town
The price is £84
includes taxes & fees
11 Nov - 12 Nov
Beppina Vacation Home, a traditional Cortona-style house, in the center, pets welcome
Dining

10. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is £77
includes taxes & fees
18 Nov - 19 Nov
Montecchio di Cortona
A building with a stone facade, multiple windows, and a balcony.

11. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is £336
includes taxes & fees
8 Dec - 9 Dec
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A window with a view of a historic town, including a prominent tower and colorful buildings.

12. "La fenêtre sur la tour" New Apartment in Castiglion Fiorentino

"La fenêtre sur la tour" New Apartment in Castiglion Fiorentino
Castiglion fiorentino
10.0 out of 10, Exceptional, (1 review)
"Large apartment 4 floors above the town. Easy walking to anywhere in the area. Great shower and large bathroom. Equipped kitchen with big refrigerator. Living room with TV and dining table and couch. Large bedroom with fan. Also, there is a hairdryer and ironing board and iron. You are very close to walk to restaurants and stores, About a mile from the train station up a hill but the hostess helped us with transport.Overall, an excellent stay for my wife and I. (Be aware the room is 4...
United States
aric w.
The price is £113
includes taxes & fees
23 Nov - 24 Nov
"La fenêtre sur la tour" New Apartment in Castiglion Fiorentino
A restaurant named 'SALUMERIA FOCACCE E VINI' with outdoor seating and a stone facade.

13. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
9.0 out of 10, Wonderful, (6 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
The price is £67
includes taxes & fees
11 Nov - 12 Nov
Limehome Arezzo Duomo
A building with a stone facade, multiple windows, and a balcony.

14. Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: il luogo che ci circondava rilassante ottimo. Cons: nulla come dicevo luogo ottimo."
Italy
Anonymous traveller
The price is £218
includes taxes & fees
30 Nov - 1 Dec
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Terrace/patio

15. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
9.0 out of 10, Wonderful, (2 reviews)
"Super søde værter. Og rigtig fint værelse. Vi kommer igen"
Denmark
Emma
The price is £95
includes taxes & fees
14 Nov - 15 Nov
Casale dell'Assiolo
A stone building with a balcony, an archway, and potted plants.

16. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Angelo was so friendly. He met us at the property and showed us around. The house is beautiful and peaceful. Thank you for a lovely stay."
United States
Bonnie B.
The price is £100
includes taxes & fees
11 Nov - 12 Nov
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

17. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (49 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
The price is £229
includes taxes & fees
11 Dec - 12 Dec
Castello di Gargonza
A large estate with multiple buildings, a swimming pool, and well-maintained gardens.

18. Holiday Home 'Magazzino 4 Superior' with Shared Pool, Wi-Fi and Air Conditioning

Holiday Home 'Magazzino 4 Superior' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
9.4 out of 10, Exceptional, (3 reviews)
"Pros: Great house, pool, and location!! Thank you!"
United States
Anonymous traveller
The price is £363
includes taxes & fees
15 Nov - 16 Nov
Holiday Home 'Magazzino 4 Superior' with Shared Pool, Wi-Fi and Air Conditioning
A large estate with multiple buildings, a swimming pool, and well-maintained gardens.

19. Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
Cortona
10.0 out of 10, Exceptional, (2 reviews)
"Pros: The spaciousness of the modern house was perfect. We felt right at home. The big pool was highly appreciated. Cons: -"
United States
Anonymous traveller
The price is £447
includes taxes & fees
11 Nov - 12 Nov
Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning
A table with food and drinks, a stone pillar, and a scenic view of hills and trees.

20. Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom

Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
Lisciano Niccone
10.0 out of 10, Exceptional, (1 review)
"Pros: The Quietness of the wonderful mornings, in the middle of Tuscan Woods. The clean and big pool with a view. The host, very friendly and engaged. a perfect vacation!"
United States
Anonymous traveller
The price is £427
includes taxes & fees
12 Nov - 13 Nov
Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
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 Portole Hotel Reviews

A terrace with sun loungers, stone walls, and potted plants.
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town

10/10 Excellent

What a beautiful hotel, the room was spacious clean and extremely well presented. All the staff were so friendly and helpful and made us feel so welcome. The breakfast was delicious and facilities great too. I loved the personal touches like the biscuits and water in the room with a note on arrival and also on the last day. We would highly recommend this hotel to anyone and thoroughly enjoyed our stay here!! :-)
United Kingdom
Julie
Reviewed May 31, 2023
Monastero di Cortona Hotel & Spa

Find out more about Portole

Everything you need to know about Portole holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portole holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Portole holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portole holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portole. 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 Portole holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portole holiday rentals we have selected for you start as low as £63 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portole rentals

At Expedia, we put the best Portole holiday 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 Portole 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 Portole holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portole. 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 holiday rentals in Portole?

Yes, there are holiday rentals close to the most popular sights in Portole, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Portole has to offer?

Holiday Home in Umbria with Pool: This holiday home rental outside of Portole offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

What can I see and do in Portole?

Explore the area and family-friendly sights such as Naturalistic Oasis La Valle, or get out into nature at a spot like Isola Maggiore. Villa Bramasole and Piazza della Repubblica are a couple of places you'll find in the wider area.

What are holiday rentals like in Portole?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portole. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for small groups.