Portole Holiday Rentals from NZ$287: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Portole has to offer?

La Dolce Collina : This holiday home rental outside of Portole is located in a rural location, and has a garden, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and kitchenware.

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Our top choices for Portole holiday rentals

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

1. B&B Piccolo Hotel

Cortona Old Town

mansoor

includes taxes & fees

2 Sept - 3 Sept

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

2. CASA AMBRA

Cortona Old Town

includes taxes & fees

17 Sept - 18 Sept

A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

3. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

Cortona Old Town

Julie R.

includes taxes & fees

1 Sept - 2 Sept

A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

4. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

includes taxes & fees

9 Sept - 10 Sept

A staircase with two lit lanterns on the wall.

5. Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Old Town

Erin

includes taxes & fees

6 Sept - 7 Sept

A black dog sitting on stone steps in front of a brown double door with a metal decorative archway.

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

Cortona Old Town

A view from a window overlooking a courtyard with stone buildings and a tower.

7. La Finestra sul Teatro

Cortona Old Town

Michelle H.

includes taxes & fees

2 Sept - 3 Sept

A park with picnic tables, a playground, and a gravel path.

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

Cortona

includes taxes & fees

3 Sept - 4 Sept

A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

9. San Michele al Borgo

Castiglion Fiorentino

Vern

includes taxes & fees

8 Sept - 9 Sept

A view through a window with a mesh screen, displaying a sunset sky and buildings in the background.

10. La casa di Laura

Cortona Old Town

"Best sleep I’ve had in a long time. Very quiet area. Beautiful views. Absolutely gorgeous. Water and coffee were provided. Clean. Bruno was very patient with us with the language barrier. We also had trouble getting to the place because we were not getting service on our phone till we connected to WiFi. Bruno met us and showed us where to park after showing us the way to the apartment. Very steep climb up to the apartment from the parking area, but Cortona is overall steep. You will climb up...

Angie F.

includes taxes & fees

14 Sept - 15 Sept

A balcony with a clear view of a distant landscape, a stone building, and a glass of orange juice.

11. Cortonas Rooftop Nest

Cortona Old Town

Robin F.

includes taxes & fees

1 Sept - 2 Sept

A window with a view of a historic town, including a prominent tower and colorful buildings.

12. The window on the tower apartment new castiglion fiorentino

Castiglion fiorentino

"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...

aric w.

includes taxes & fees

1 Sept - 2 Sept

13. iConic Wellness Resort

Arezzo

Rheymarie

includes taxes & fees

2 Sept - 3 Sept

A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

14. Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

includes taxes & fees

1 Sept - 2 Sept

15. Montecchio di Cortona

Montecchio

Monica S.

includes taxes & fees

1 Sept - 2 Sept

A hot tub in a grassy outdoor area with a mountain view.

16. Farmhouse with mountain views hot tub

Cortona

includes taxes & fees

2 Sept - 3 Sept

17. Casale dell'Assiolo

Castiglione del Lago

includes taxes & fees

7 Sept - 8 Sept

A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

18. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

includes taxes & fees

4 Sept - 5 Sept

A swimming pool with stone edges, surrounded by greenery and a view of a hill with a castle-like structure in the background.

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

Cortona (AR)

Anonymous traveller

includes taxes & fees

14 Sept - 15 Sept

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Top Portole Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"The hotel was amazing and the staff very friendly and helpful. The breakfast was spectacular. we really enjoyed ourselves at this hotel and in the city of Cortona."

Relais Villa Baldelli

8/10 Good

"The property was relaxing and quaint. The pool was nice and the overall Tuscan country vibe and decor was nice. The location was good and the rooms were spacious. It was not walkable to anything but if you have a rental car the location is great because Cortana is a wonderful town. The staff is kind and responsive however I had an issue with the cleaning ladies where they disposed of thing of my mine thinking it was trash. I found it odd that cleaning folks would take it upon themselves to touch my things as all. I asked them to not to clean our room anymore and they did it again the next day due to poor internal communication. It was annoying to deal with that but still I would say the staff tried their best to be helpful. Lastly, I was not a fan of their breakfast. They had the basics that were heavily rooted in sweets and pork both of which I don’t eat. They made fresh plain eggs but some veggies and maybe turkey meat would have been nice. Overall, for the price point this place is good."

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!!"

Find out more about Portole

Everything you need to know about Portole holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portole holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portole holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portole holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portole holiday rentals we have selected for you start as low as NZ$287 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portole rentals

At Expedia, we put the best Portole holiday 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 holiday.

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 holiday rentals in Portole?

Yes, there are holiday rentals close to the most popular sights in Portole, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Portole has to offer?

La Dolce Collina: This holiday home rental outside of Portole is located in a rural location, and has a garden, 1 hot tub and a BBQ 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 Maria Nuova are a couple of places you'll find in the wider area.

What are holiday rentals like in Portole?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portole. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for small groups.

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Check prices for these dates

Our top choices for Portole holiday rentals

1. B&B Piccolo Hotel

2. CASA AMBRA

3. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

4. Vicolo Della Scala Rooms - La Luna

5. Cortona Shabby Chic House<br>(Independent & balcony)

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

7. La Finestra sul Teatro

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

9. San Michele al Borgo

10. La casa di Laura

11. Cortonas Rooftop Nest

12. The window on the tower apartment new castiglion fiorentino

13. iConic Wellness Resort

14. Happy Nest Tuscany Between Florence and Rome

15. Montecchio di Cortona

16. Farmhouse with mountain views hot tub

17. Casale dell'Assiolo

18. Artisti del Cavallo Tourism

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

Find holiday rentals that suit your style

Top Portole Hotel Reviews

Monastero di Cortona Hotel & Spa

Precise Tale Poggio Alla Sala

Relais Villa Grazianella - UNA Esperienze

Poggio Paradiso Resort & Spa

Relais Villa Baldelli

Villa di Piazzano - Small Luxury Hotel of the World

Il Gentiluomo Hotel & SPA

Hotel Minerva

Villa Tiberini Wine Relais

Find out more about Portole

Frequently asked questions

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