Portland Holiday Rentals

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Holiday Rentals in Portland

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (62)
"Great hotel"
The price is AU$507
includes taxes & fees
15 June - 16 June
The Weldon Hotel

In-town no frills 2 bedroom apt

6.0 out of 10, (2)
"The frills of the neighborhood carried into the apartment. Floors and bathrooms seemed clean. Dishes and Keurig filthy - broken window a/c on floor. Broken chairs. No tlc for the property. Neighborhood beyond the stated description- would not recommend . Best to say is that rental car made it out with all windows and tires. Very disappointed "
The price is AU$315
includes taxes & fees
23 June - 24 June
In-town no frills 2 bedroom apt

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (106)
"Very comfortable, close to shopping and restaurants, clean, easily accessible"
The price is AU$793
includes taxes & fees
13 July - 14 July
City Amenities, Casco Bay Sunrises and Natural Beauty

Ocean view Victorian

9.8 out of 10, Exceptional, (88)
"Everything about the stay was fantastic. Great location and responsive host. "
Ocean view Victorian

Studio Apartment near downtown Walkable!

6.0 out of 10, (1)
"The listing said "Studio Apartment," but it is really just a bedroom with a bath. A mini-fridge, coffeemaker and microwave oven do not make this a "Studio" in the sense that I understand that word (i.e., a one-room apartment with kitchen and bath). When I went back and looked at the photos in the listing, that should have been obvious to me, but I got hung up on the word "Studio."That said, it was a comfortable room, although the bathroom was stingy on towels (no face cloths, only one hand...
The price is AU$353
includes taxes & fees
22 June - 23 June
Studio Apartment near downtown Walkable!

Cozy and Quiet beautiful home 1 Bedroom private bathroom Portland with WiFi, AC

2.0 star property
Cozy and Quiet beautiful home 1 Bedroom private bathroom Portland with WiFi, AC

Bright & Sunny West End Apartment with Private Parking.

9.8 out of 10, Exceptional, (30)
"Just as described. Good walkable location. Clean and quaint. Recommend!"
The price is AU$728
includes taxes & fees
23 June - 24 June
Bright & Sunny West End Apartment with Private Parking.

Studio Unit Walkable Everywhere

The price is AU$287
includes taxes & fees
23 June - 24 June
Studio Unit Walkable Everywhere

Charming Studio apartment with WiFi, AC in welcoming Portland

10.0 out of 10, Exceptional, (1)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is AU$358
includes taxes & fees
22 June - 23 June
Charming Studio apartment with WiFi, AC in welcoming Portland

Private Entrance Residential Portland

8.0 out of 10, Very good, (1)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
The price is AU$234
includes taxes & fees
15 June - 16 June
Private Entrance Residential Portland

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (101)
"Perfect location. Wonderful accommodations"
The price is AU$481
includes taxes & fees
15 June - 16 June
Adorable Portland getaway on the Eastern Promenade

Knock on Wood | Airy Charm in Heart of Downtown

9.6 out of 10, Exceptional, (14)
"Great location!! It’s roomy and was a great home base for our trip."
The price is AU$729
includes taxes & fees
1 July - 2 July
Knock on Wood | Airy Charm in Heart of Downtown

Completely remodeled 2 bedroom apartment in Portland's West End

10.0 out of 10, Exceptional, (62)
"Met all of our expectations, in a great location!"
The price is AU$702
includes taxes & fees
15 June - 16 June
Completely remodeled 2 bedroom apartment in Portland's West End

Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

10.0 out of 10, Exceptional, (43)
"Great little spot - parking was a little challenging but we managed"
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

Bright and Fresh Back Cove4 Bedroom, Sleeps 8. Airmatress for additional 2.

9.8 out of 10, Exceptional, (61)
"Great location and great amenities."
Bright and Fresh Back Cove4 Bedroom, Sleeps 8. Airmatress for additional 2.

Beautiful, single story ranch. Next to city park with ocean view!

8.4 out of 10, Very good, (7)
"Great vacation rental!"
Beautiful, single story ranch. Next to city park with ocean view!

Large 1 bed w/ private deck

The price is AU$321
includes taxes & fees
14 June - 15 June
Large 1 bed w/ private deck

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

10.0 out of 10, Exceptional, (12)
"We had a lovely weekend staying at this condo! It was clean, cozy, and the coffee bar was amazing! "
The price is AU$836
includes taxes & fees
15 June - 16 June
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Prime City Living Townhouse by RedAwning

2.0 star property
8.6 out of 10, Excellent, (4)
"We enjoyed the apartment - it was great to be able to relax and hang out together.. the stairs were a challenge, but we managed. You might think of a way to put a railing at the very tops of the landing on the 3rd floor- the stairs are narrow and step. A couple of small issues - one window over the kitchen sink was missing the handle to crank it closed. It was great Fri night when it was warm - but kind of chilly the rest of the weekend. The emailed instructions gave us the wrong wi-fi...
The price is AU$969
includes taxes & fees
15 June - 16 June
Prime City Living Townhouse by RedAwning

Charming Downtown Penthouse - The Cabana

9.0 out of 10, Wonderful, (14)
"Myself and a few friends stayed one night and the apartment was clean and comfortable and just what we needed."
The price is AU$698
includes taxes & fees
17 June - 18 June
Charming Downtown Penthouse - The Cabana
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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Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals in Portland close to Bayside Bowl, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Portland speak highly of the bustling port and array of shops. The acclaimed theatre scene and great live music are some other things you might like to check out during your trip.

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

Cozy and Quiet beautiful home 1 Bedroom private bathroom Portland with WiFi, AC: This highly rated holiday home rental in Portland is located on the beach, and offers a fireplace, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Portland?

Choose from 146 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Bayside Bowl and Portland Observatory are a couple of the family-friendly sights, whereas cultural attractions include Merrill Auditorium and Portland Museum of Art. While here, Casco Bay Lines Ferry Terminal and Cross Insurance Arena are other places worth a visit.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for small groups.