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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for South Portland holiday rentals

A modern living room with a grey sofa, a small glass table, and a woven rug. There is a kitchen area with a white countertop and hanging lights.

1. 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 HK$1,051
HK$2,377 total
includes taxes & fees
29 Oct - 30 Oct
Willard Beach: Cozy Apartment with a King Size Bed
A black console table with a mirror above it, a lamp, and a potted plant beside it.

2. 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, (13 reviews)
The price is HK$1,515
HK$2,617 total
includes taxes & fees
1 Nov - 2 Nov
Peaceful & minutes from the Old Port with private parking
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

3. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (37 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
The price is HK$1,546
HK$2,558 total
includes taxes & fees
19 Oct - 20 Oct
Sunny Spot with Private Parking.
A beach with a wooden chair and a small building in the background.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (71 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is HK$2,161
HK$4,400 total
includes taxes & fees
8 Nov - 9 Nov
Arlie`s Digs! - One Block To Willard Beach!
A hallway leading to a living room with a sofa, a lamp, and a window.

5. The Coastal Connection

The Coastal Connection
Thorton Heights
7.2 out of 10, Good, (7 reviews)
"Very convenient, comfortable, and bright apartment. We appreciated that dogs were allowed as well."
United States
Sheryl S.
The price is HK$788
HK$2,433 total
includes taxes & fees
9 Nov - 10 Nov
The Coastal Connection
A building named Willard Square with a storefront and a red vehicle parked outside.

6. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is HK$2,354
HK$4,743 total
includes taxes & fees
15 Oct - 16 Oct
Willard Square Family Home
A coastal view with a house, a tree, and a beach.

7. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard By the Sea - 30 ft to the beach- 2nd floor
Willard
10.0 out of 10, Exceptional, (15 reviews)
"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."
United States
Gerald B.
The price is HK$2,089
HK$4,842 total
includes taxes & fees
3 Nov - 4 Nov
Willard By the Sea - 30 ft to the beach- 2nd floor
A dining table with chairs, a potted plant, and decorative items.

8. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (9 reviews)
"Location and parking were perfect for our first visit to Portland"
United States
Linda
The price is HK$1,122
HK$2,463 total
includes taxes & fees
25 Oct - 26 Oct
Willard Beach–Apartment Near Portland & Parks
A beach with clear water, people swimming, and houses in the background.

9. Willard By the Sea - 30 ft to the beach

Willard By the Sea - 30 ft to the beach
Willard
9.8 out of 10, Exceptional, (8 reviews)
"Superb beach-side location. AND as we were there during a heat wave, well air conditioned!!Complete amenities, well furnished for two couples or one with children. Short drive to Portland waterfront and all its activities.Pricing is a bit high, but the seaside location justifies the premium."
United States
Gerald B.
The price is HK$1,951
HK$4,400 total
includes taxes & fees
9 Nov - 10 Nov
Willard By the Sea - 30 ft to the beach
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

10. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (125 reviews)
"Really nice room and location"
United States
Victoria
The price is HK$1,512
HK$2,236 total
includes taxes & fees
2 Nov - 3 Nov
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

11. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (15 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
The price is HK$2,572
HK$3,981 total
includes taxes & fees
10 Nov - 11 Nov
Evalina Hotel
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

12. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (21 reviews)
"We had a great stay in Portland! The place was just as described and the hosts were easy to communicate with. A good place for a couple nights within walking distance of all Portland has to offer."
United States
Lucy T.
The price is HK$618
HK$1,181 total
includes taxes & fees
1 Nov - 2 Nov
Studio Apartment near downtown Walkable!
A living room with a sofa, armchairs, a coffee table, and a potted plant.

13. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.8 out of 10, Excellent, (33 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is HK$726
HK$1,433 total
includes taxes & fees
9 Nov - 10 Nov
Beautiful 1st Floor Apartment & Amazing Shower
A house with a wooden staircase leading to a door marked with the number 50.

14. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (107 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 HK$890
HK$2,116 total
includes taxes & fees
3 Nov - 4 Nov
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

15. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is HK$981
HK$1,805 total
includes taxes & fees
1 Nov - 2 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.4 out of 10, Exceptional, (93 reviews)
"Excellent property in Portland. Clean with amenities needed for any stay. Easy access to downtown. Hosts communicate exceptionally well and property is everything it promotes!"
United States
Adam Y.
The price is HK$997
HK$3,200 total
includes taxes & fees
26 Oct - 27 Oct
Walk to Old Port ♦ West End Condo ♦ Parking
A narrow pathway leading to a wooden house with a porch, surrounded by lush greenery and trees.

17. King Size Bed - West End Studio - Walk to Old Port

King Size Bed - West End Studio - Walk to Old Port
West End
The price is HK$1,063
HK$2,296 total
includes taxes & fees
1 Nov - 2 Nov
King Size Bed - West End Studio - Walk to Old Port
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

18. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (2 reviews)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
The price is HK$589
HK$760 total
includes taxes & fees
25 Oct - 26 Oct
Great suburban location close to town!
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

19. 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, (62 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is HK$890
HK$3,057 total
includes taxes & fees
29 Oct - 30 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A modern house with a wooden exterior, a small garden, and a visible window.

20. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is HK$1,096
HK$3,700 total
includes taxes & fees
19 Oct - 20 Oct
Spacious and Contemporary Condo in the Heart of Portland - Close to 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

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

8/10 Good
"The room was clean & staff was very friendly & helpful"
Sue 1-night trip
Posted 10 hours ago
Quality Inn & Suites South Portland

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?

Charming 110-year former Inn 10' from the Ocean!: This highly rated holiday home rental in South Portland is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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 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 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.