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. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (11 reviews)
"Location and parking were perfect for our first visit to Portland"
United States
Linda
Willard Beach–Apartment Near Portland & Parks

2. Peaceful & minutes from Old Port w/private parking

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is NZ$634
includes taxes & fees
2 Nov - 3 Nov
Peaceful & minutes from Old Port w/private parking

3. Sunny Spot with Private Parking

Sunny Spot with Private Parking
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
The price is NZ$453
includes taxes & fees
2 Nov - 3 Nov
Sunny Spot with Private Parking

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, (73 reviews)
"Great stay!"
United States
Jason M.
The price is NZ$888
includes taxes & fees
18 Nov - 19 Nov
Arlie`s Digs! - One Block To Willard Beach!

5. 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, (16 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 NZ$883
includes taxes & fees
17 Nov - 18 Nov
Willard By the Sea - 30 ft to the beach- 2nd floor

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 NZ$1,122
includes taxes & fees
12 Nov - 13 Nov
Willard Square Family Home

7. 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

8. The Coastal Connection by Everrow

The Coastal Connection by Everrow
Thorton Heights
7.2 out of 10, Good, (7 reviews)
"The house was amazing! Close enough to the towns but secluded enough we could truly relax."
United States
Michelle M.
The price is NZ$556
includes taxes & fees
1 Dec - 2 Dec
The Coastal Connection by Everrow

9. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (128 reviews)
"Really nice room and location"
United States
Victoria
The price is NZ$482
includes taxes & fees
16 Nov - 17 Nov
The Weldon Hotel

10. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (16 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 NZ$741
includes taxes & fees
2 Dec - 3 Dec
Evalina Hotel

11. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (25 reviews)
"Location was convenient to everything and building was super secure."
United States
Rose
The price is NZ$216
includes taxes & fees
12 Nov - 13 Nov
Studio Apartment near downtown Walkable!

12. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (29 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
The price is NZ$255
includes taxes & fees
2 Nov - 3 Nov
Bright & Spacious Apartment with Amazing Shower

13. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.2 out of 10, Wonderful, (5 reviews)
"We were staying here for the sake of being able to see a show at Good Theater. The theater itself ended up being within walking distance, and same for a few different places to eat! This worked out great for our plans :)"
United States
Kaley
The price is NZ$139
includes taxes & fees
19 Nov - 20 Nov
Great suburban location close to town!

14. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (34 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is NZ$255
includes taxes & fees
5 Nov - 6 Nov
Beautiful 1st Floor Apartment & Amazing Shower

15. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.0 out of 10, Very good, (17 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
The price is NZ$144
includes taxes & fees
29 Nov - 30 Nov
Portland 1-bedroom with enclosed porch & parking

16. 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 NZ$385
includes taxes & fees
3 Nov - 4 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.4 out of 10, Exceptional, (95 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 NZ$621
includes taxes & fees
2 Nov - 3 Nov
Walk to Old Port ♦ West End Condo ♦ Parking

18. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is NZ$620
includes taxes & fees
2 Nov - 3 Nov
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

19. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (108 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 NZ$456
includes taxes & fees
3 Nov - 4 Nov
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

20. Luxury Condo Downtown Portland Old Port

Luxury Condo Downtown Portland Old Port
Downtown Portland
9.6 out of 10, Exceptional, (24 reviews)
"Super cute apartment that was perfect for our stay in Portland. It was close to Old Port that had lots of cute shops and restaurants."
United States
Erin
The price is NZ$592
includes taxes & fees
30 Nov - 1 Dec
Luxury Condo Downtown Portland Old Port
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our South Portland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up South Portland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in South Portland. Seeing all the best attractions is bound to make you fall in love with South Portland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in South Portland short-term rentals, that won’t be hard to do.

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.