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. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (11 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is AU$548
includes taxes & fees
15 Sept - 16 Sept
Peaceful & minutes from the Old Port with private parking

2. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
The price is AU$518
includes taxes & fees
16 Aug - 17 Aug
Willard Beach–Apartment Near Portland & Parks

3. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (31 reviews)
"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 AU$447
includes taxes & fees
1 Sept - 2 Sept
Sunny Spot with Private Parking.

4. The Coastal Connection

The Coastal Connection
Thorton Heights
7.6 out of 10, Good, (5 reviews)
"Nice clean apartment very updated in older building. 3 Units or so in this renovated house. So expect to hear your neighbors. Also the main road has a lot of traffic at every hour. Semis shake the house. "
United States
Benjamin
The price is AU$555
includes taxes & fees
8 Sept - 9 Sept
The Coastal Connection

5. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is AU$821
includes taxes & fees
23 Aug - 24 Aug
Willard Square Family Home

6. Forest City Oasis and Spa

Forest City Oasis and Spa
Pleasantdale
10.0 out of 10, Exceptional, (4 reviews)
"Spacious apartment with lovely patio and gardens."
United States
Kathryn S.
The price is AU$1,110
includes taxes & fees
21 Aug - 22 Aug
Forest City Oasis and Spa

7. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (68 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is AU$928
includes taxes & fees
7 Sept - 8 Sept
Arlie`s Digs! - One Block To Willard Beach!

8. Willard Beach: Cozy Apartment with a King Size Bed

Willard Beach: Cozy Apartment with a King Size Bed
Willard Beach
10.0 out of 10, Exceptional, (2 reviews)
"Lovely and quiet. Just what I had hoped for. "
United States
Heather R.
The price is AU$511
includes taxes & fees
2 Sept - 3 Sept
Willard Beach: Cozy Apartment with a King Size Bed

9. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (109 reviews)
"Really nice room and location"
United States
Victoria
The price is AU$552
includes taxes & fees
1 Sept - 2 Sept
The Weldon Hotel

10. Waterfront Two Master Suite Penthouse with Rooftop

Waterfront Two Master Suite Penthouse with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (200 reviews)
"We’ve stayed here several times and have had a wonderful experience each time. The property was clean and comfortable and the host was very responsive. Highly recommended!"
United States
Arthur B.
The price is AU$2,188
includes taxes & fees
28 Aug - 29 Aug
Waterfront Two Master Suite Penthouse with Rooftop

11. Penthouse Two Master Waterfront Suite with Rooftop

Penthouse Two Master Waterfront Suite with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (267 reviews)
"This was one of the most spectacular places we have ever stayed. The views are amazing and the place is just incredible. We really look forward to our next visit!"
United States
Daryl R.
The price is AU$2,375
includes taxes & fees
29 Aug - 30 Aug
Penthouse Two Master Waterfront Suite with Rooftop

12. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (105 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
The price is AU$373
includes taxes & fees
31 Aug - 1 Sept
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

13. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (9 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is AU$1,012
includes taxes & fees
31 Aug - 1 Sept
Evalina Hotel

14. Downtown Penthouse Suite - Stunning Harbor Views

Downtown Penthouse Suite - Stunning Harbor Views
Downtown Portland
10.0 out of 10, Exceptional, (235 reviews)
"Amazing property and location. Perfect to explore the old port."
United States
Kevin P.
The price is AU$1,728
includes taxes & fees
27 Aug - 28 Aug
Downtown Penthouse Suite - Stunning Harbor Views

15. Incredible Location! Heart of Old Port/Spacious Apartment

Incredible Location! Heart of Old Port/Spacious Apartment
Downtown Portland
10.0 out of 10, Exceptional, (45 reviews)
"Great stay, beautiful place and perfect location. "
United States
Heather P.
The price is AU$1,576
includes taxes & fees
17 Aug - 18 Aug
Incredible Location! Heart of Old Port/Spacious Apartment

16. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place. Good location."
United States
Rob M.
The price is AU$585
includes taxes & fees
3 Sept - 4 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

17. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (88 reviews)
"Host was very responsive, and helpful. Location is amazing for walking the city."
United States
Chris P.
The price is AU$572
includes taxes & fees
7 Sept - 8 Sept
Walk to Old Port ♦ West End Condo ♦ Parking

18. Historic Home in the West End. Private Parking.

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (59 reviews)
"Perfect cozy apartment for a get away! Great location that’s walkable for shopping, brunch, and coffee and less than a 15 minute drive from everything else on our itinerary!"
United States
Callie R.
The price is AU$515
includes taxes & fees
7 Sept - 8 Sept
Historic Home in the West End. Private Parking.

19. Stylish Brownstone Downtown Free St|Perfect Getaway for 2

Stylish Brownstone Downtown Free St|Perfect Getaway for 2
Downtown Portland
10.0 out of 10, Exceptional, (43 reviews)
"What a great stay! The rental property was absolutely fantastic! Can't wait to come back! Highly recommend staying here. "
United States
Ken C.
The price is AU$1,049
includes taxes & fees
21 Aug - 22 Aug
Stylish Brownstone Downtown Free St|Perfect Getaway for 2

20. Prime Old Port 3BR • Free Parking • Sleeps 8

Prime Old Port 3BR • Free Parking • Sleeps 8
Downtown Portland
9.8 out of 10, Exceptional, (164 reviews)
"Everything was great! Excellent location, clean and great communication. Thank you!"
United States
Stephanie W.
The price is AU$1,634
includes taxes & fees
19 Aug - 20 Aug
Prime Old Port 3BR • Free Parking • Sleeps 8
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 favourite 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 depend 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 AU$255 per night. Entering your travel dates in the search wizard might find you 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 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 Bug Light and Maine Mall.

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.