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Portole Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ￥22,256
￥24,833 total
includes taxes & fees
Nov 2 - Nov 3
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
9.8 out of 10, Exceptional, (9 reviews)
"Nice property"
United States
Joseph
The price is ￥16,430
￥17,133 total
includes taxes & fees
Nov 2 - Nov 3
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

3. 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 ￥21,826
￥24,712 total
includes taxes & fees
Oct 28 - Oct 29
San Michele al Borgo
Pool

4. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ￥11,646
￥13,865 total
includes taxes & fees
Nov 18 - Nov 19
iConic Wellness Resort
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
The price is ￥21,702
￥25,392 total
includes taxes & fees
Oct 27 - Oct 28
Cortona Shabby Chic House<br>(Independent & Balcony)
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

6. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is ￥34,865
￥38,615 total
includes taxes & fees
Nov 11 - Nov 12
CASA AMBRA
A narrow cobblestone street lined with stone buildings, some with balconies and potted plants.

7. Stone house villa with Spa in Cortona

Stone house villa with Spa in Cortona
Cortona Old Town
9.0 out of 10, Wonderful, (40 reviews)
"Villa Letizia is a hidden gem! The views of Lake Trasimeno are absolutely breathtaking, especially during sunset, The garden area is perfect for lounging, and the hammock was my favorite spot to unwind with a book,"
Germany
Anonymous traveler
Stone house villa with Spa in Cortona
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.
The price is ￥23,565
￥27,607 total
includes taxes & fees
Nov 8 - Nov 9
Cortonas Rooftop Nest
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

9. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
The price is ￥38,537
￥43,094 total
includes taxes & fees
Oct 27 - Oct 28
Fontelunga Hotel & Villas
A restaurant named 'SALUMERIA FOCACCE E VINI' with outdoor seating and a stone facade.

10. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
9.0 out of 10, Wonderful, (4 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 ￥11,387
￥15,601 total
includes taxes & fees
Oct 28 - Oct 29
Limehome Arezzo Duomo
A window with a view of a historic town, including a prominent tower and colorful buildings.

11. "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 ￥17,573
￥24,602 total
includes taxes & fees
Oct 26 - Oct 27
"La fenêtre sur la tour" New Apartment in Castiglion Fiorentino
A building with a stone facade, multiple windows, and a balcony.

12. 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 traveler
The price is ￥34,718
￥42,027 total
includes taxes & fees
Oct 26 - Oct 27
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

13. Lovely apartment for 2 people with WIFI, A/C and pets allowed

Lovely apartment for 2 people with WIFI, A/C and pets allowed
Cortona Old Town
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥17,096
￥17,799 total
includes taxes & fees
Nov 2 - Nov 3
Lovely apartment for 2 people with WIFI, A/C and pets allowed
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

14. 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
The price is ￥12,493
￥14,446 total
includes taxes & fees
Oct 26 - Oct 27
Artisti del Cavallo Tourism
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.
The price is ￥13,882
￥17,045 total
includes taxes & fees
Nov 2 - Nov 3
Montecchio di Cortona
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

16. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ￥7,908
￥11,774 total
includes taxes & fees
Oct 26 - Oct 27
Happy Nest Tuscany Between Florence and Rome
A modern hotel room with large windows, a bed, a desk, and a chair.

17. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.2 out of 10, Very good, (84 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
The price is ￥11,073
￥13,234 total
includes taxes & fees
Nov 3 - Nov 4
B&B 52cento
A view of a historic town with prominent buildings and a church tower.

18. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (195 reviews)
"Pros: Nice staff. Good breakfast with a nice view. Cons: Old bed and can feel the metal springs in your back so poor sleep. Lots of beggars and vagrants at the entrance of building."
United States
Steven
The price is ￥13,966
￥16,416 total
includes taxes & fees
Nov 1 - Nov 2
Cameracaffè Centro
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

19. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (48 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 ￥37,941
￥42,438 total
includes taxes & fees
Oct 26 - Oct 27
Castello di Gargonza
Terrace/patio

20. 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 ￥17,637
￥20,104 total
includes taxes & fees
Nov 5 - Nov 6
Casale dell'Assiolo
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

Podere La Rocca

Podere La Rocca

10/10 Excellent
"Clean"
Gloria 3-night trip
Posted 2 days ago
Podere La Rocca

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:

  • View our selection of featured holiday rentals in Portole
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  • Enter your travel dates to view the best deals on holiday rentals in Portole while they last

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?

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 Piazza della Repubblica 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.