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

South Portland Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for South Portland vacation rentals

Outdoor dining

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 SAR 927
SAR 1,502 total
includes taxes & fees
4 Sep - 5 Sep
Peaceful & minutes from the Old Port with private parking
Interior

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 SAR 822
SAR 1,575 total
includes taxes & fees
26 Aug - 27 Aug
Willard Beach–Apartment Near Portland & Parks
Interior

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 SAR 740
SAR 1,228 total
includes taxes & fees
1 Sep - 2 Sep
Sunny Spot with Private Parking.
TV

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 SAR 669
SAR 1,536 total
includes taxes & fees
8 Sep - 9 Sep
The Coastal Connection
Exterior

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 SAR 1,126
SAR 2,269 total
includes taxes & fees
23 Aug - 24 Aug
Willard Square Family Home
Outdoor dining

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 SAR 1,816
SAR 3,021 total
includes taxes & fees
21 Aug - 22 Aug
Forest City Oasis and Spa
Beach nearby

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 SAR 1,464
SAR 2,643 total
includes taxes & fees
7 Sep - 8 Sep
Arlie`s Digs! - One Block To Willard Beach!
Smart TV, fireplace, books

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 SAR 689
SAR 1,410 total
includes taxes & fees
2 Sep - 3 Sep
Willard Beach: Cozy Apartment with a King Size Bed
Deluxe Suite, 1 King Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

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 SAR 1,082
SAR 1,461 total
includes taxes & fees
1 Sep - 2 Sep
The Weldon Hotel
TV, fireplace

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 SAR 4,110
SAR 6,051 total
includes taxes & fees
17 Aug - 18 Aug
Waterfront Two Master Suite Penthouse with Rooftop
TV, stereo

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.
Penthouse Two Master Waterfront Suite with Rooftop
Exterior detail

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
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
Front of property

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 SAR 1,986
SAR 2,728 total
includes taxes & fees
31 Aug - 1 Sep
Evalina Hotel
Dining

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 SAR 3,300
SAR 4,813 total
includes taxes & fees
27 Aug - 28 Aug
Downtown Penthouse Suite - Stunning Harbor Views
Interior

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 SAR 2,610
SAR 4,322 total
includes taxes & fees
18 Aug - 19 Aug
Incredible Location! Heart of Old Port/Spacious Apartment
Interior

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 SAR 560
SAR 1,629 total
includes taxes & fees
3 Sep - 4 Sep
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Flat-screen TV, Netflix, books, streaming services

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)
"It was what we were looking for- in Portland, with a parking spot. Some nice restaurants nearby- walking distance! Note the bathroom is on the first floor, bedrooms are on second. Modest but had everything we needed! What we were disappointed in was we had no idea how many museums and local attractions in a city are closed till the end of April or May! "
United States
Susan R.
The price is SAR 501
SAR 1,561 total
includes taxes & fees
1 Sep - 2 Sep
Walk to Old Port ♦ West End Condo ♦ Parking
Interior

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 SAR 852
SAR 1,412 total
includes taxes & fees
7 Sep - 8 Sep
Historic Home in the West End. Private Parking.
Smart TV

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

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 SAR 1,235
SAR 2,824 total
includes taxes & fees
16 Aug - 17 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

Long Creek Hotel by IHG

Long Creek Hotel by IHG

8/10 Good
"Hotel under renovations. Pool and hot tub area definitely needs updating. Staff friendly. Our room was old, but im sure will be updated with renovation. Comfortable lobby and outside area."
wendy 2-night trip
Posted less than an hour ago
Long Creek Hotel by IHG

Frequently asked questions

Can I find vacation rentals in South Portland?

Yes, you can find vacation rentals close to the most popular sights in South Portland, or you can choose a more secluded option if you'd like a relaxing place to 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 vacation home rentals in South Portland?

Quintessential Maine Beach Cottage: Visitors like this South Portland vacation home rental. It is located on the beach and has a private yard, a selection of games, and a barbecue grill 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 you can cook with friends or family.

How many vacation rentals are there in South Portland?

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

What can I see and do in South Portland?

Cultural attractions include South Portland Historical Society Museum and Lyric Music Theater, 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 vacation rentals like in South Portland?

Vacation rentals are private properties you can reserve for several days or longer in South Portland. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.