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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for South Portland holiday rentals

A hallway leading to a living room with a sofa, a lamp, and a window.

1. 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$1,093
HK$2,790 total
includes taxes & fees
30 Sept - 1 Oct
The Coastal Connection
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)
"Cute, convenient spot!"
United States
Kelly S.
The price is HK$1,937
HK$3,103 total
includes taxes & fees
27 Sept - 28 Sept
Peaceful & minutes from the Old Port with private parking
A beach with a wooden chair and a small building in the background.

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is HK$2,313
HK$4,564 total
includes taxes & fees
20 Oct - 21 Oct
Arlie`s Digs! - One Block To Willard Beach!
A dining table with chairs, a potted plant, and decorative items.

4. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (7 reviews)
"Excellent in every way."
United States
Robert B.
The price is HK$1,346
HK$2,792 total
includes taxes & fees
29 Sept - 30 Sept
Willard Beach–Apartment Near Portland & Parks
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

5. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (33 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$1,545
HK$2,531 total
includes taxes & fees
29 Sept - 30 Sept
Sunny Spot with Private Parking.
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.

6. 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
A building named Willard Square with a storefront and a red vehicle parked outside.

7. 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$2,353
HK$4,741 total
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home
A beach with clear water, people swimming, and houses in the background.

8. 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, (7 reviews)
"Our host was available and helpful, everything clean and great location"
United States
Janet H.
The price is HK$3,210
HK$5,934 total
includes taxes & fees
20 Oct - 21 Oct
Willard By the Sea - 30 ft to the beach
A coastal view with a house, a tree, and a beach.

9. 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)
"We really enjoyed our stay. It was comfortable and clean. Cute decor and right by a great beach. Would stay there again and recommend it to others."
United States
Millicent W.
The price is HK$4,547
HK$7,904 total
includes taxes & fees
5 Oct - 6 Oct
Willard By the Sea - 30 ft to the beach- 2nd floor
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

10. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.0 out of 10, Very good, (13 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is HK$659
HK$830 total
includes taxes & fees
28 Sept - 29 Sept
Portland 1-bedroom with enclosed porch & parking
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

11. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (19 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
The price is HK$700
HK$1,263 total
includes taxes & fees
6 Oct - 7 Oct
Studio Apartment near downtown Walkable!
A gym with treadmills, elliptical machines, and exercise balls.

12. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.2 out of 10, Wonderful, (19 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is HK$1,127
HK$1,399 total
includes taxes & fees
27 Sept - 28 Sept
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

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

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (28 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is HK$1,012
HK$1,838 total
includes taxes & fees
20 Oct - 21 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland
A modern house with a wooden exterior, a small garden, and a visible window.

14. 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$1,095
HK$3,664 total
includes taxes & fees
4 Oct - 5 Oct
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A living room with a sofa, armchairs, a coffee table, and a potted plant.

15. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is HK$1,199
HK$1,948 total
includes taxes & fees
27 Sept - 28 Sept
Beautiful 1st Floor Apartment & Amazing Shower
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

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 and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is HK$889
HK$3,047 total
includes taxes & fees
19 Oct - 20 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

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, (91 reviews)
"Was great for our few days in Portland! Having a designated parking space was great and the location was convenient for everything we wanted to do."
United States
Britney G.
The price is HK$1,359
HK$3,542 total
includes taxes & fees
6 Oct - 7 Oct
Walk to Old Port ♦ West End Condo ♦ Parking
A modern living room with a sofa, a small table, and a TV.

18. Brand New 1 Bedroom Apartment in Portland

Brand New 1 Bedroom Apartment in Portland
West End
10.0 out of 10, Exceptional, (52 reviews)
"Great host communication, super clean and good location!"
United States
Lorraine V.
The price is HK$1,640
HK$3,369 total
includes taxes & fees
30 Sept - 1 Oct
Brand New 1 Bedroom Apartment in Portland
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (85 reviews)
"It was nice if you like being right in town. There is no view and it's a bit noisy."
United States
Nancy S.
The price is HK$1,318
HK$3,974 total
includes taxes & fees
8 Oct - 9 Oct
Elegant condo - walk to Portland's best restaurants & Old Port
A street lined with buildings, one with a red door and a sign that reads "MINATO".

20. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (147 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is HK$1,388
HK$2,257 total
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"We loved how old the inn was and how it was restored. Our room was so spacious and clean. We loved this place and would highly recommend!!! One thing, steep stairs but definitely worth it. Breakfast was good and staff was great. We loved it"
denise 1-night trip
Posted 1 hour ago
Inn at St John Portland In-Town

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 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 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.