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Portole Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Portole vacation rentals

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

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
B&B Piccolo Hotel
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
$205 nightly
The price is $227
Nov 8 - Nov 9
Total with taxes and fees
CASA AMBRA
Pool

3. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (44 reviews)
"It was wonderful!"
United States
Wade
$74 nightly
The price is $88
Nov 8 - Nov 9
Total with taxes and fees
iConic Wellness Resort
A breakfast setting with a fireplace, a table with plates, glasses, and a croissant.

4. 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
$133 nightly
The price is $151
Nov 9 - Nov 10
Total with taxes and fees
San Michele al Borgo
A hotel room with a bed, a desk with a chair, a wardrobe, a television, and a window with curtains.

5. 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
$77 nightly
The price is $90
Nov 9 - Nov 10
Total with taxes and fees
Limehome Arezzo Duomo
A balcony with potted plants and a view of a cityscape.

6. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (195 reviews)
"Very convenient and a beautifull terrasse to have breakfast with an amazing vue on Arezzo!"
France
Alexandre
$90 nightly
The price is $105
Nov 9 - Nov 10
Total with taxes and fees
Cameracaffè Centro
A bedroom with a large bed, a chandelier, a mirror, and plants.

7. Bibi Boutique

Bibi Boutique
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
"The BiBi was perfect for my needs. Its location is excellent, and the room had all the needed amenities. Fabio was a gracious host, orienting me to Arezzo and recommending a wonderful trattoria close by. I highly recommend and hope to return!"
United States
Carol
$79 nightly
The price is $94
Nov 8 - Nov 9
Total with taxes and fees
Bibi Boutique
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

8. 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
$75 nightly
The price is $87
Nov 12 - Nov 13
Total with taxes and fees
Artisti del Cavallo Tourism
Terrace/patio

9. 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
$112 nightly
The price is $127
Nov 14 - Nov 15
Total with taxes and fees
Casale dell'Assiolo
A hotel room with a large bed, a fireplace, and a brick ceiling.

10. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$108 nightly
The price is $124
Nov 8 - Nov 9
Total with taxes and fees
DormiVeglia B&B
A modern hotel room with large windows, a bed, a desk, and a chair.

11. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.2 out of 10, Very good, (85 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
$77 nightly
The price is $92
Nov 11 - Nov 12
Total with taxes and fees
B&B 52cento
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

12. 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
$271 nightly
The price is $302
Nov 8 - Nov 9
Total with taxes and fees
Castello di Gargonza
A building entrance with a number '10' sign, a potted plant with flowers, and a staircase leading to the entrance.

13. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$93 nightly
The price is $104
Nov 28 - Nov 29
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
A narrow stone-walled room with a wooden table and blue upholstered chairs.

14. Allegra Toscana - Affittacamere & Guest House Arezzo

Allegra Toscana - Affittacamere & Guest House Arezzo
Arezzo Centro Storico
7.0 out of 10, Good, (17 reviews)
"Great location in Arezzo, easy and simple to find and access. Everything was exactly as we needed although we did not need to stay long."
United Kingdom
Justin
$86 nightly
The price is $105
Nov 9 - Nov 10
Total with taxes and fees
Allegra Toscana - Affittacamere & Guest House Arezzo
A stone building with a balcony and a small garden area with plants.

15. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
$63 nightly
The price is $69
Nov 11 - Nov 12
Total with taxes and fees
L'Antica Sosta
An arched stone bridge with a white building on the right, featuring a balcony with plants.

16. Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (21 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
$101 nightly
The price is $111
Nov 14 - Nov 15
Total with taxes and fees
Locanda Antico Borgo
A rustic brick building with a mural, a clock, and various potted plants.

17. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
$96 nightly
The price is $106
Dec 8 - Dec 9
Total with taxes and fees
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

18. Rustic Holiday Home in Citta di Castello With Swimming Pool

Rustic Holiday Home in Citta di Castello With Swimming Pool
Città di Castello
$226 nightly
The price is $242
Nov 10 - Nov 11
Total with taxes and fees
Rustic Holiday Home in Citta di Castello With Swimming Pool
Property entrance

19. Palazzo Tarlati Residenza d'Epoca

Palazzo Tarlati Residenza d'Epoca
Civitella in Val di Chiana
8.0 out of 10, Very good, (3 reviews)
"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...
United States
Marco
$162 nightly
The price is $178
Nov 8 - Nov 9
Total with taxes and fees
Palazzo Tarlati Residenza d'Epoca
A building entrance with a number '10' sign, a potted plant with flowers, and a staircase leading to the entrance.

20. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
$108 nightly
The price is $123
Dec 8 - Dec 9
Total with taxes and fees
Vicolo Della Scala Rooms - Il Sole
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

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa

10/10 Excellent
"Staff"
Danielle 2-night trip
Posted 1 day ago
Poggio Paradiso Resort & Spa

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 $166 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 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.