Portland Holiday Rentals

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Holiday Rentals in Portland

The Weldon Hotel

4.0 star property
9.6 out of 10, Exceptional, (38)
"Very clean and comfortable! "
The price is AU$263
includes taxes & fees
9 Mar - 10 Mar
The Weldon Hotel

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (93)
"Perfect location. Wonderful accommodations"
The price is AU$298
includes taxes & fees
26 Feb - 27 Feb
Adorable Portland getaway on the Eastern Promenade

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (145)
"Old friends (in age and longevity of relationships) met up in Portland for a weekend getaway. Great location. Great city. Enjoyed our time exploring the city culture and restaurants within easy reach but also spent long hours in the bright living room catching up over a pit of tea."
The price is AU$349
includes taxes & fees
26 Feb - 27 Feb
Glorious getaway on Portland's Eastern Promenade.

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries

Cozy, Elegant and Bright 2 bed in the East End

9.8 out of 10, Exceptional, (36)
"Very clean. Nice walk along bikepath to downtown. Will look to stay here again. Loved the neighborhood and parking was easy. Kitchen had everything we needed to cook. "
The price is AU$573
includes taxes & fees
27 Feb - 28 Feb
Cozy, Elegant and Bright 2 bed in the East End

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (99)
"Very comfortable, close to shopping and restaurants, clean, easily accessible"
The price is AU$556
includes taxes & fees
3 Mar - 4 Mar
City Amenities, Casco Bay Sunrises and Natural Beauty

Prime City Living Townhouse by RedAwning

2.0 star property
8.0 out of 10, Very good, (1)
"It was very convenient. "
The price is AU$779
includes taxes & fees
2 Mar - 3 Mar
Prime City Living Townhouse by RedAwning

Entire Historic Home - Portland West End

10.0 out of 10, Exceptional, (1)
Entire Historic Home - Portland West End

Incredible Location! Heart of Old Port|Roomy Condo

10.0 out of 10, Exceptional, (25)
"Great location for a fun Old Port get away. Property manager was very responsive."
Incredible Location! Heart of Old Port|Roomy Condo

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (60)
"Great layout, well-appointed and super walkable to Old Port, the great restos on Washington and the Eastern Promenade. Only downside was communication with Vacasa: they always answered but didn’t necessarily address the issue, ie I struggled with the electronic door lock, was leaving for the weekend, they said the owner would come address it but when I returned 3 days later it had been left unlocked all weekend. Unreliable WiFi & I work remotely. Several times had to work from cafes.beautifully...
The price is AU$644
includes taxes & fees
26 Feb - 27 Feb
Elegant condo - walk to Portland's best restaurants & Old Port

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (101)
"We stayed to visit family in the area. The location was excellent and we loved the ocean view. Everything was very clean, except under the sofa in the living room. We searched for a dropped puzzle piece and "
Gorgeous ocean-front home with stunning beach views

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"Owner should get new cleaners. House smelled like dog urine. Bathroom smelled like human urine. Had to clean floors and bathroom…lots of dirt…not sure the last time floors were I’m mopped. Dog hair on sheets. Beds were not comfortable so be prepared. Parking is a challenge. One paid parking spot in front ($36/day). Can park super close to house for 2nd spot. Owner not very responsive. Had to constantly message for arrival info and didn’t get it until 10 mins after checkin time. No instructions...
100 feet from the ocean 3 bedroom cottage 420 friendly

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (124)
"Great location! If you are looking for quiet time during the evening hours this isn’t the place for you as The Brunswick restaurant is directly below. If you like music and a great view, it’s an amazing spot! "
The price is AU$355
includes taxes & fees
3 Mar - 4 Mar
Oceanfront Condo! Spectacular Views From Private Large Balcony

Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

10.0 out of 10, Exceptional, (88)
"Seadrift is a perfect place for a family get together. Spacious, comfortable, and fully equipped with every possible necessity, this beach house gave us everything we needed to enjoy a memorable five nights of total relaxation. Thank you, Patrick and Olivia"
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (198)
"Great codo unit, very close to everything "
The price is AU$546
includes taxes & fees
27 Mar - 28 Mar
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.4 out of 10, Exceptional, (26)
"This 2 bedroom cottage was perfect for our 3 day stay.Location was a 10 minute walk to the boardwalk.Would like to come back in the summer."
The price is AU$345
includes taxes & fees
27 Mar - 28 Mar
Large 2BD cottage 10 min to Pier & Beach Pets ok

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (30)
"This property was spectacular! Beautiful views, clean, spacious and comfortable. Great space to share with a larger group. The Host was very responsive. It was an amazing experience even in the winter. "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (40)
"Great place.... Very clean and everything you will need to stay. It was three levels and it had supplies needed for the beach (Beach wagon, chairs, towel, sand toys...). We stayed off season so most of the houses were vacant. We would definately come back again. I did send two messages to the owner, but did not get a response. "
The price is AU$792
includes taxes & fees
26 Feb - 27 Feb
Beach House ∆ Prime Location ∆ Steps to the Ocean

Quintessential Maine Beach Cottage

10.0 out of 10, Exceptional, (105)
"Great spot, the dog loved it too"
Quintessential Maine Beach Cottage

Historic Kennebunkport home only 0.3 miles to Dock Square

10.0 out of 10, Exceptional, (64)
"Our family of 5 spent a couple of nights in this home full of magical charm for a holiday getaway. House was clean, cozy, with books to read and cozy blankets. We adored the sweet touches such as the Christmas tree and decor throughout. A welcome bag and snacks was most appreciated. Would definitely come again"
The price is AU$787
includes taxes & fees
26 Feb - 27 Feb
Historic Kennebunkport home only 0.3 miles to Dock Square
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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Other types of properties in Portland you may be interested in

The Westin Portland Harborview

4.0 star property
8.8 out of 10, Excellent, (1004)
"Great stay"
The price is AU$158
includes taxes & fees
13 Mar - 14 Mar
The Westin Portland Harborview

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1464)
"Friendly staff and nice hotel! Great location!"
The price is AU$272
includes taxes & fees
16 Mar - 17 Mar
Portland Harbor Hotel

Ramada Plaza by Wyndham Portland

3.0 star property
7.6 out of 10, Good, (1024)
"Always great staff 😃 "
The price is AU$165
includes taxes & fees
23 Mar - 24 Mar
Ramada Plaza by Wyndham Portland
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.

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 fascinating museums and entertainment choices 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?

The Globe House on Munjoy Hill - Walk to Breweries: This highly rated holiday home rental in Portland is located in the city centre, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Portland?

Choose from 120 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 Wadsworth-Longfellow House. 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.