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Portole Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Portole 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 ￥23,013
￥26,059 total
includes taxes & fees
Jul 30 - Jul 31
B&B Piccolo Hotel
Property grounds

City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"This place was such a great find! So central and easily reachable. We really enjoyed our stay!"
United States
Julie R.
The price is ￥17,417
￥18,162 total
includes taxes & fees
Jul 28 - Jul 29
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is ￥15,462
￥17,753 total
includes taxes & fees
Aug 3 - Aug 4
Vicolo Della Scala Rooms - La Luna
Interior

La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (38 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
The price is ￥24,309
￥36,789 total
includes taxes & fees
Jul 28 - Jul 29
La Finestra sul Teatro
Exterior

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 ￥21,733
￥24,651 total
includes taxes & fees
Jul 28 - Jul 29
San Michele al Borgo
Interior

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 ￥23,005
￥26,917 total
includes taxes & fees
Jul 28 - Jul 29
Cortona Shabby Chic House<br>(Independent & balcony)
Property grounds

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 ￥26,656
￥30,754 total
includes taxes & fees
Jul 28 - Jul 29
Cortonas Rooftop Nest
Outdoor dining

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥11,735
￥15,088 total
includes taxes & fees
Jul 28 - Jul 29
Holiday home with panoramic terrace ideal for families and couples
Exterior detail

Vacation home Beppina, typical cortonese house, in the center, animals welcome

Vacation home Beppina, typical cortonese house, in the center, animals welcome
Cortona Old Town
The price is ￥15,522
￥19,531 total
includes taxes & fees
Jul 28 - Jul 29
Vacation home Beppina, typical cortonese house, in the center, animals welcome
Outdoor spa tub

Farmhouse with mountain views hot tub

Farmhouse with mountain views hot tub
Cortona
The price is ￥38,000
￥73,899 total
includes taxes & fees
Aug 2 - Aug 3
Farmhouse with mountain views hot tub
Interior

The window on the tower apartment new castiglion fiorentino

The window on the tower apartment new 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 ￥18,628
￥26,079 total
includes taxes & fees
Jul 28 - Jul 29
The window on the tower apartment new castiglion fiorentino
Private kitchen

Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ￥15,088
￥19,186 total
includes taxes & fees
Jul 28 - Jul 29
Happy Nest Tuscany Between Florence and Rome
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is ￥17,839
￥20,368 total
includes taxes & fees
Jul 29 - Jul 30
Vicolo Della Scala Rooms - Il Sole
Pool

Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi

Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Cortona (AR)
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Die Anlage strahlt einen wunderbaren nostalgischen Charme aus. Elisa hat sich hervorragend um uns gekümmert. Per Whatsapp wurden sämtliche Fragen in Kürze geklärt. Cons: Die Terrasse ist kaum zu nützen, da vor allem am Abend die Mückenplage unangenehm ist. Die Fenster und Türen der Wohnung haben alle Fliegen- und Mückengitter."
Germany
Anonymous traveler
Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Exterior

Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy

Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Cortona
10.0 out of 10, Exceptional, (28 reviews)
"Great location with gorgeous views over the Chiana hills, and nearby restaurants. We enjoyed discovering Cortona and several hill towns in the ares"
United States
Patricia H.
The price is ￥93,867
￥107,401 total
includes taxes & fees
Aug 11 - Aug 12
Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Property grounds

Cosy apartment for 2 guests with WIFI, A/C and pets allowed

Cosy apartment for 2 guests with WIFI, A/C and pets allowed
Cortona Old Town
10.0 out of 10, Exceptional, (1 review)
The price is ￥18,385
￥19,130 total
includes taxes & fees
Jul 31 - Aug 1
Cosy apartment for 2 guests with WIFI, A/C and pets allowed
Dining

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 ￥14,716
￥19,000 total
includes taxes & fees
Aug 10 - Aug 11
Montecchio di Cortona
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 ￥20,881
￥24,087 total
includes taxes & fees
Aug 25 - Aug 26
iConic Wellness Resort
Pool

Apartment "Papà Giuseppe La Colombaia" with Shared Pool and Wi-Fi

Apartment "Papà Giuseppe La Colombaia" with Shared Pool and Wi-Fi
Cortona
6.0 out of 10, (2 reviews)
"We didn’t actually get the property posted, he mentioned there was no gas so put us up at another property. That being said, the property we agreed to change to was older, very dirty and not worth what we paid. I was very disappointed but thankfully it was only one night."
United States
Amanda C.
The price is ￥29,238
￥29,983 total
includes taxes & fees
Jul 28 - Jul 29
Apartment "Papà Giuseppe La Colombaia" with Shared Pool and Wi-Fi
TV

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 traveler
The price is ￥30,847
￥39,229 total
includes taxes & fees
Aug 25 - Aug 26
Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning
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

Villa Tiberini Wine Relais

Villa Tiberini Wine Relais

10/10 Excellent
"We stayed four nights at Villa Tiberini and loved it! Everyone was super friendly and helpful, nice breakfast with delicious eggs, the apartment was beautiful with everything we needed and the grounds were beautiful. We especially loved the pool. It’s in a great position for exploring near by. Highly recommended!!"
Sadie 4-night trip
Posted 18 hours ago
Villa Tiberini Wine Relais

Find out more about Portole

Search for holiday rentals in Portole on Expedia! You can easily find your home rentals, villas, holiday apartments in Portole 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 Portole!

Frequently asked questions

Can I find vacation rentals in Portole?

Yes, we have vacation rentals near top attractions in Portole, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Portole?

La Dolce Collina: You might want to consider this vacation rental near Portole, which is located in a rural location and has a garden, a hot tub, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and kitchenware.

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 Cortona Cathedral are a couple of places you'll find in the larger area.

What are vacation rentals like in Portole?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Portole. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip.