A lighthouse, rocky coastline, and a sunset over the ocean.

South Portland Holiday Rentals

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Our top choices for South Portland holiday rentals

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (107 reviews)
"Really nice room and location"
United States
Victoria
The price is NZ$708
includes taxes & fees
1 Sept - 2 Sept
The Weldon Hotel

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (7 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is NZ$1,388
includes taxes & fees
1 Sept - 2 Sept
Evalina Hotel

3. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is NZ$629
includes taxes & fees
5 Aug - 6 Aug
Fortland Island Campground

4. 1/2 Mi to Pier: Wfh-friendly Apt in Maine!

1/2 Mi to Pier: Wfh-friendly Apt in Maine!
3.0 star property
Old Orchard Beach
The price is NZ$574
includes taxes & fees
26 Aug - 27 Aug
1/2 Mi to Pier: Wfh-friendly Apt in Maine!

5. Beachfront Condotel on Oob, Steps From Downtown

Beachfront Condotel on Oob, Steps From Downtown
3.0 star property
Old Orchard Beach
The price is NZ$664
includes taxes & fees
18 Aug - 19 Aug
Beachfront Condotel on Oob, Steps From Downtown

6. Steps to Sandy Beach! Oceanfront Old Orchard Gem

Steps to Sandy Beach! Oceanfront Old Orchard Gem
3.0 star property
Old Orchard Beach
The price is NZ$627
includes taxes & fees
24 Aug - 25 Aug
Steps to Sandy Beach! Oceanfront Old Orchard Gem

7. 'beachfront 14' Condo on Old Orchard Beach

'beachfront 14' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is NZ$629
includes taxes & fees
23 Aug - 24 Aug
'beachfront 14' Condo on Old Orchard Beach

8. 1/2 Mi to Ocean: Cozy Apt in Old Orchard Beach

1/2 Mi to Ocean: Cozy Apt in Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is NZ$607
includes taxes & fees
24 Aug - 25 Aug
1/2 Mi to Ocean: Cozy Apt in Old Orchard Beach

9. 'beachfront 9' Condo on Old Orchard Beach

'beachfront 9' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is NZ$629
includes taxes & fees
26 Aug - 27 Aug
'beachfront 9' Condo on Old Orchard Beach

10. Walk to Pier & Ocean: Apt in Old Orchard Beach!

Walk to Pier & Ocean: Apt in Old Orchard Beach!
4.0 star property
Old Orchard Beach
6.0 out of 10, (1 review)
"This is an old house, and certain features could be deemed charming. The beds were comfortable, and we appreciated some of the amenities. However, it seemed worn and bare-bones in some aspects. For example, the AC in one of the bedrooms was a stand-alone unit that was jerry-rigged to vent out the window, and the other bedroom had no AC. The screen door was broken. There were hardly any utensils and no bowls. The hairdryer “high” setting was broken and could only be used on “low”. For only a...
United States
Lawrence
The price is NZ$552
includes taxes & fees
31 Aug - 1 Sept
Walk to Pier & Ocean: Apt in Old Orchard Beach!
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 South Portland Hotel Reviews

Find out more about South Portland

Everything you need to know about South Portland 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 South Portland 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 South Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Portland. 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 South Portland 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 South Portland holiday rentals we have selected for you start as low as NZ$322 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Portland rentals

At Expedia, we put the best South Portland 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 South Portland 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 South Portland 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 South Portland. 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 South Portland?

Yes, there are holiday rentals close to the most popular sights in South Portland, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in South Portland. Allow some time to check out the waterfront during your trip.

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

New Listing. 2BR+Bonus Sleeping Room in OOB. Walk to Beach & Amusement Park.: This holiday home rental outside of South Portland is located near the beach, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in South Portland?

With 26 Expedia holiday rentals, you're guaranteed to find just the right place for your South Portland stay.

What can I see and do in South Portland?

Cultural attractions include Lyric Music Theater and South Portland Historical Society Museum, whereas Willard Beach and Casco Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Maine Mall and Fort Preble.

What are holiday rentals like in South Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Portland. Holiday rentals feature extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family gatherings.