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Portole Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Portole vacation rentals

Lobby

1. 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
$160 nightly
The price is $180
Aug 11 - Aug 12
Total with taxes and fees
B&B Piccolo Hotel
Property grounds

2. 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.
$108 nightly
The price is $113
Aug 10 - Aug 11
Total with taxes and fees
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Apartment (1 Bedroom) | Front of property

3. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$99 nightly
The price is $114
Aug 26 - Aug 27
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
Interior

4. 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.
$244 nightly
The price is $249
Sep 2 - Sep 3
Total with taxes and fees
La Finestra sul Teatro
Interior

5. 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
$171 nightly
The price is $175
Aug 28 - Aug 29
Total with taxes and fees
Cortona Shabby Chic House<br>(Independent & balcony)
Outdoor dining

6. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
$94 nightly
The price is $94
Aug 19 - Aug 20
Total with taxes and fees
Holiday home with panoramic terrace ideal for families and couples
Exterior detail

7. 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
$122 nightly
The price is $126
Aug 19 - Aug 20
Total with taxes and fees
Vacation home Beppina, typical cortonese house, in the center, animals welcome
Exterior

8. 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
$129 nightly
The price is $147
Aug 10 - Aug 11
Total with taxes and fees
San Michele al Borgo
Property grounds

9. 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.
$189 nightly
The price is $192
Aug 17 - Aug 18
Total with taxes and fees
Cortonas Rooftop Nest
Outdoor spa tub

10. Farmhouse with mountain views hot tub

Farmhouse with mountain views hot tub
Cortona
$459 nightly
The price is $459
Aug 10 - Aug 11
Total with taxes and fees
Farmhouse with mountain views hot tub
Pool

11. 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
$677 nightly
The price is $681
Sep 8 - Sep 9
Total with taxes and fees
Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
Junior Suite | Terrace/patio

12. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
$116 nightly
The price is $132
Sep 1 - Sep 2
Total with taxes and fees
Casale dell'Assiolo
Apartment (1 Bedroom) | Front of property

13. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
$111 nightly
The price is $126
Aug 11 - Aug 12
Total with taxes and fees
Vicolo Della Scala Rooms - Il Sole
Interior

14. 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.
$160 nightly
The price is $162
Aug 10 - Aug 11
Total with taxes and fees
The window on the tower apartment new castiglion fiorentino
Dining

15. 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.
$112 nightly
The price is $112
Aug 19 - Aug 20
Total with taxes and fees
Montecchio di Cortona
Private kitchen

16. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
$79 nightly
The price is $83
Sep 2 - Sep 3
Total with taxes and fees
Happy Nest Tuscany Between Florence and Rome
Property grounds

17. Cosy apartment for 2 people with A/C, WIFI and pets allowed

Cosy apartment for 2 people with A/C, WIFI and pets allowed
Cortona Old Town
10.0 out of 10, Exceptional, (1 review)
$112 nightly
The price is $117
Aug 10 - Aug 11
Total with taxes and fees
Cosy apartment for 2 people with A/C, WIFI and pets allowed
TV

18. 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
$258 nightly
The price is $258
Aug 29 - Aug 30
Total with taxes and fees
Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning
Exterior

19. 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, (29 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.
$661 nightly
The price is $661
Aug 11 - Aug 12
Total with taxes and fees
Stunning Private House: fantastic pool, beautiful views, A/C, Wi-Fi, and privacy
Exterior

20. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very Good, (24 reviews)
"Good house for one night. "
Germany
Heiner
$82 nightly
The price is $95
Aug 10 - Aug 11
Total with taxes and fees
Artisti del Cavallo Tourism
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

Nuovo Etruria Resort

Nuovo Etruria Resort

10/10 Excellent
"Missed the entrance as it’s not very well sign posted. Amazing views, Pool was great, great staff. The room was very very hot upstairs, there was only an aircon downstairs, which meant the kids were fine, but we were baked by the morning. Other than that, faultless."
Ant 1-night trip
Posted 1 day ago
Nuovo Etruria Resort

Find out more about Portole

Everything you need to know about Portole 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 Portole vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portole vacation 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 low season months. For more hustle and bustle, you may prefer to visit Portole in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $218 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Portole rentals

At Expedia, we put the best Portole 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 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 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 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 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 Santa Margherita Basilica 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.