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

South Portland Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for South Portland holiday rentals

Outdoor dining

1. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is HK$1,938
HK$3,129 total
includes taxes & fees
4 Sept - 5 Sept
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 HK$2,830
HK$4,573 total
includes taxes & fees
5 Sept - 6 Sept
Willard Beach–Apartment Near Portland & Parks
Exterior

3. 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.
Willard Square Family Home
Outdoor dining

4. Forest City Oasis and Spa

Forest City Oasis and Spa
Pleasantdale
10.0 out of 10, Exceptional, (2 reviews)
"Very charming. It is an apartment on lower floor so there are some upstairs noises but not too bad. The garden is wonderful. Very clean"
United States
Susan M.
The price is HK$3,271
HK$5,665 total
includes taxes & fees
21 Aug - 22 Aug
Forest City Oasis and Spa
Interior

5. 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 HK$1,545
HK$2,548 total
includes taxes & fees
1 Sept - 2 Sept
Sunny Spot with Private Parking.
Living area

6. SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Ligonia
10.0 out of 10, Exceptional, (2 reviews)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is HK$4,785
HK$8,892 total
includes taxes & fees
26 Aug - 27 Aug
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
TV

7. 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 HK$1,457
HK$3,281 total
includes taxes & fees
7 Sept - 8 Sept
The Coastal Connection
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.
Willard Beach: Cozy Apartment with a King Size Bed
Private kitchen

9. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (108 reviews)
"Really nice room and location"
United States
Victoria
The price is HK$2,541
HK$3,359 total
includes taxes & fees
1 Sept - 2 Sept
The Weldon Hotel
Interior

10. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (23 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is HK$1,545
HK$2,505 total
includes taxes & fees
31 Aug - 1 Sept
Charming Studio apartment with WiFi, AC in welcoming Portland
Beach

11. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
City Amenities, Casco Bay Sunrises and Natural Beauty
Egyptian cotton sheets, premium bedding, down duvets, bed sheets

12. 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 HK$2,736
HK$2,982 total
includes taxes & fees
23 Aug - 24 Aug
Fortland Island Campground
Front of property

13. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (8 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is HK$4,278
HK$5,839 total
includes taxes & fees
31 Aug - 1 Sept
Evalina Hotel
TV, fireplace

14. 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 HK$8,620
HK$12,688 total
includes taxes & fees
28 Aug - 29 Aug
Waterfront Two Master Suite Penthouse with Rooftop
Smart TV

15. Eastbayside/Munjoy - Charming Downtown Escape

Eastbayside/Munjoy - Charming Downtown Escape
East Bayside
9.8 out of 10, Exceptional, (37 reviews)
"Very nice location, clean and comfortable!"
United States
Ryan R.
The price is HK$4,201
HK$7,041 total
includes taxes & fees
14 Aug - 15 Aug
Eastbayside/Munjoy - Charming Downtown Escape
Smart TV

16. Newly Renovated 2nd Floor Apt near USM

Newly Renovated 2nd Floor Apt near USM
Oakdale
10.0 out of 10, Exceptional, (17 reviews)
"Per the title great location, cleanliness as advertised."
United States
Edub
The price is HK$3,914
HK$5,361 total
includes taxes & fees
13 Aug - 14 Aug
Newly Renovated 2nd Floor Apt near USM
Dining

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (81 reviews)
"I had a wonderful week at this perfect place. Met my expectations and way more. So walkable all over Portland. I will be back. Thank you so very much."
United States
Margaret H.
The price is HK$1,318
HK$4,025 total
includes taxes & fees
23 Aug - 24 Aug
Elegant condo - walk to Portland's best restaurants & Old Port
Interior

18. Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.4 out of 10, Exceptional, (34 reviews)
"Perfect location for walking around the Old Port. Incredible value and exactly what we needed for a weekend away. Would definitely come back. "
United States
Michael M.
Skyline 138: Charming West End Mansard Penthouse
Interior

19. 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 HK$1,781
HK$2,924 total
includes taxes & fees
7 Sept - 8 Sept
Historic Home in the West End. Private Parking.
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 HK$2,580
HK$5,838 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

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

10/10 Excellent
"Rooms were clean, breakfast was solid, fitness center was a bit small & air conditioning wasn’t working in there"
Namrata 2-night trip
Posted less than an hour ago
Comfort Inn South Portland Airport

Find out more about South Portland

Search for holiday rentals in South Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in South Portland using one of the methods below:

  • View our selection of featured holiday rentals in South Portland
  • Use the map to find apartments and other holiday homes in the South Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Portland while they last

Look no further and take a look at our great range of rental properties in South Portland!

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.