South Portland Holiday Rentals

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Our top choices for South Portland holiday rentals

9.8 out of 10, Exceptional, (7)
"Super Cute little apartment! My only complaint, is the parking. It gets a little tight. And the bed is a little firm for my liking, but overall it was super nice and convenient!"
United States
Samantha
The price is NZ$336
includes taxes & fees
11 Dec - 12 Dec
Peaceful & minutes from the Old Port with private parking

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (24)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is NZ$341
includes taxes & fees
22 Dec - 23 Dec
Sunny Spot with Private Parking.

Apartment in Thorton Heights

The Coastal Connection
2.0 star property
The price is NZ$544
includes taxes & fees
14 Dec - 15 Dec
The Coastal Connection
10.0 out of 10, Exceptional, (61)
"We had a wonderful week here. Fantastic proximity to the beach & a great bakery and ice cream shop. They accommodated us and our dog very well and had everything we need for a great stay. "
United States
Elizabeth C.
The price is NZ$547
includes taxes & fees
16 Dec - 17 Dec
Arlie`s Digs! - One Block To Willard Beach!

Holiday Home in South Portland

Modern Getaway by the Sea
10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
The price is NZ$768
includes taxes & fees
11 Dec - 12 Dec
Modern Getaway by the Sea
9.6 out of 10, Exceptional, (4)
"Enjoyed our stay, perfect for 2 kids and parents. Outdoor shower was a great addition for our beach days!"
United States
Greg R.
The price is NZ$846
includes taxes & fees
11 Dec - 12 Dec
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2

Holiday Home in Willard Beach

Willard Square Family Home
9.6 out of 10, Exceptional, (9)
"Thoroughly enjoyed this house! "
United States
David W.
The price is NZ$1,089
includes taxes & fees
13 Dec - 14 Dec
Willard Square Family Home
The price is NZ$1,132
includes taxes & fees
18 Dec - 19 Dec
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
10.0 out of 10, Exceptional, (13)
"Great area, close to the beach, water views, close to Portland, and everything in the apartment worked really well. There has been a lot of attention paid as to what would make a guest's stay really awesome. "
United States
David F.
The price is NZ$962
includes taxes & fees
11 Dec - 12 Dec
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
9.6 out of 10, Exceptional, (127)
"Very convenient location. Comfortable accommodation! I would stay here again. "
United States
Cynthia W.
The price is NZ$281
includes taxes & fees
11 Dec - 12 Dec
Adorable Portland getaway on the Eastern Promenade
10.0 out of 10, Exceptional, (11)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The price is NZ$275
includes taxes & fees
11 Dec - 12 Dec
The Outlet Studio, Rustic Comfort w Fireplace
10.0 out of 10, Exceptional, (6)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is NZ$379
includes taxes & fees
11 Dec - 12 Dec
Modern, Luxurious Cabin in the Woods - 03
8.0 out of 10, Very good, (24)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is NZ$373
includes taxes & fees
15 Dec - 16 Dec
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
2.0 star property
10.0 out of 10, Exceptional, (24)
"Sweet place! "
United States
Lisa G.
The price is NZ$345
includes taxes & fees
11 Dec - 12 Dec
Pine Point Beach private, quaint, charming studio.
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is NZ$272
includes taxes & fees
14 Dec - 15 Dec
Beautiful 1st Floor Apartment & Amazing Shower
10.0 out of 10, Exceptional, (3)
"The location was wonderful! The host was so communicative and kind!"
United States
Courtney W.
The price is NZ$339
includes taxes & fees
6 Jan - 7 Jan 2026
Adorable 1 bedroom cabin only 50 ft from beach#1
10.0 out of 10, Exceptional, (16)
"Super cute spot! Wonderful girls weekend!"
United States
Diana M.
The price is NZ$464
includes taxes & fees
10 Jan - 11 Jan 2026
West End Bright Spot with Parking.
10.0 out of 10, Exceptional, (15)
"The property was exactly as advertised, and it was a perfect two night stay for us on a road trip up the Maine coast with our dogs. The location was perfect to explore Portland, Saco, Biddeford, and Kennebunkport. The hosts were super responsive and friendly. We would definitely stay here again in future!"
United States
Ryan S.
The price is NZ$486
includes taxes & fees
11 Dec - 12 Dec
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
9.6 out of 10, Exceptional, (26)
"Easy check-in, super clean, amazing location! "
United States
Chantelle V.
The price is NZ$355
includes taxes & fees
18 Dec - 19 Dec
Escape to the Beach! Cozy Condo in downtown OOB.
10.0 out of 10, Exceptional, (55)
"It was clean and neat and just steps to the beach. It had everything you could possibly need."
United States
Mare E.
The price is NZ$833
includes taxes & fees
17 Dec - 18 Dec
Beach House ∆ Prime Location ∆ Steps to the Ocean
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$233 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?

Quintessential Maine Beach Cottage: This holiday home rental outside of South Portland is located on the beach, and has a private garden, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in South Portland?

With 30 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 Bug Light.

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.