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Portole Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Portole 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

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$156 nightly
The price is $176
Sep 29 - Sep 30
Total with taxes and fees
B&B Piccolo Hotel
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

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)
"Beautiful location. Can't wait to go back."
United States
Dawn H.
$107 nightly
The price is $112
Sep 28 - Sep 29
Total with taxes and fees
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
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

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$97 nightly
The price is $112
Sep 30 - Oct 1
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
A swimming pool with stone edges, surrounded by greenery and a view of a hill with a castle-like structure in the background.

4. 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
$645 nightly
The price is $650
Sep 25 - Sep 26
Total with taxes and fees
Holiday Apartment "Monastero" with Mountain View, Shared Pool & Wi-Fi
A staircase with two lit lanterns on the wall.

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
$162 nightly
The price is $165
Sep 24 - Sep 25
Total with taxes and fees
Cortona Shabby Chic House<br>(Independent & balcony)
A view from a window overlooking a courtyard with stone buildings and a tower.

6. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (39 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
$205 nightly
The price is $210
Oct 4 - Oct 5
Total with taxes and fees
La Finestra sul Teatro
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

7. 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
$126 nightly
The price is $144
Oct 17 - Oct 18
Total with taxes and fees
San Michele al Borgo
A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

8. 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.
$211 nightly
The price is $214
Sep 28 - Sep 29
Total with taxes and fees
Cortonas Rooftop Nest
A hot tub in a grassy outdoor area with a mountain view.

9. Farmhouse with mountain views hot tub

Farmhouse with mountain views hot tub
Cortona
$455 nightly
The price is $455
Sep 27 - Sep 28
Total with taxes and fees
Farmhouse with mountain views hot tub
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

10. CASA AMBRA

CASA AMBRA
Cortona Old Town
$292 nightly
The price is $324
Oct 1 - Oct 2
Total with taxes and fees
CASA AMBRA
A modern apartment with a kitchen, dining area, living room, and a balcony.

11. 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
$221 nightly
The price is $221
Sep 30 - Oct 1
Total with taxes and fees
Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

12. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
$72 nightly
The price is $77
Sep 24 - Sep 25
Total with taxes and fees
Happy Nest Tuscany Between Florence and Rome
A park with picnic tables, a playground, and a gravel path.

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

Holiday home with panoramic terrace ideal for families and couples
Cortona
$93 nightly
The price is $93
Sep 24 - Sep 25
Total with taxes and fees
Holiday home with panoramic terrace ideal for families and couples
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

14. 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)
$111 nightly
The price is $116
Sep 28 - Sep 29
Total with taxes and fees
Cosy apartment for 2 guests with WIFI, A/C and pets allowed
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

15. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
$282 nightly
The price is $315
Oct 22 - Oct 23
Total with taxes and fees
Fontelunga Hotel & Villas
A fountain with water cascading down a column, surrounded by greenery and a building in the background.

16. Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (39 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
$94 nightly
The price is $108
Sep 24 - Sep 25
Total with taxes and fees
Residence al Lago
A window with a view of a historic town, including a prominent tower and colorful buildings.

17. 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.
$158 nightly
The price is $160
Sep 30 - Oct 1
Total with taxes and fees
The window on the tower apartment new castiglion fiorentino

18. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (40 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
$81 nightly
The price is $96
Oct 20 - Oct 21
Total with taxes and fees
iConic Wellness Resort
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

19. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
$81 nightly
The price is $94
Sep 27 - Sep 28
Total with taxes and fees
Artisti del Cavallo Tourism
A stone house with a swimming pool, outdoor seating, and a well-lit patio area.

20. Villa in Tuscany with Pool and Valley Views

Villa in Tuscany with Pool and Valley Views
Castiglion Fiorentino
9.4 out of 10, Exceptional, (28 reviews)
"Enjoyed swimming every day of our stay!"
United States
Anonymous traveler
Villa in Tuscany with Pool and Valley Views
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

8/10 Good
"The staff was very attentive and helpful specially Alfredo. He is terrific! My only complaint was a persistent low level hum that was noticeable at night, I figured that our room was above the kitchen area and that it was the industrial size refrigerator below. The view of the town up the hill from our room was spectacular. Decent breakfast. The pool was wonderful."
Robert 2-night trip
Posted 14 hours 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 $178 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?

Holiday Home in Umbria with Pool: Visitors like this Portole vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection 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 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.