South Portland Holiday Rentals

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Check prices for these dates

Tonight
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Holiday Rentals in South Portland

Dining
Sunny Spot with Private Parking.
Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (24)
"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$754
HK$1,559 total
includes taxes & fees
2 Nov - 3 Nov
Sunny Spot with Private Parking.
Interior
Willard Beach–Private Apt Near Portland & Parks
Willard Beach–Private Apt Near Portland & Parks
10.0 out of 10, Exceptional, (4)
"Excellent in every way."
United States
Robert B.
The price is HK$710
HK$1,841 total
includes taxes & fees
28 Oct - 29 Oct
Willard Beach–Private Apt Near Portland & Parks
Outdoor dining
Peaceful & minutes from the Old Port with private parking
Peaceful & minutes from the Old Port with private parking
9.8 out of 10, Exceptional, (7)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
The price is HK$956
HK$1,923 total
includes taxes & fees
11 Nov - 12 Nov
Peaceful & minutes from the Old Port with private parking
On the beach, sun-loungers, beach towels
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
9.6 out of 10, Exceptional, (4)
"I cannot say enough about the location! Our two families rented the upstairs and downstairs units, and were very happy with our stay. Great communication with the owner, well-appointed, comfortable beds. Would definitely stay here again. "
United States
Julie W.
The price is HK$2,129
HK$4,591 total
includes taxes & fees
5 Nov - 6 Nov
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
Private kitchen
Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
The price is HK$1,523
HK$4,803 total
includes taxes & fees
11 Nov - 12 Nov
Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Property grounds
Willard Square Family Home
Willard Square Family Home
9.6 out of 10, Exceptional, (8)
"A funky place. Liked the decor. "
United States
Gerald H.
Willard Square Family Home
Fridge, microwave, oven, stovetop
Willard Beach: Cozy Apartment with a King Size Bed
Willard Beach: Cozy Apartment with a King Size Bed
10.0 out of 10, Exceptional, (1)
"Lovely and quiet. Just what I had hoped for. "
United States
Heather R.
The price is HK$838
HK$1,990 total
includes taxes & fees
30 Oct - 31 Oct
Willard Beach: Cozy Apartment with a King Size Bed
On the beach, sun-loungers, beach towels
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
10.0 out of 10, Exceptional, (13)
"Great area, close to the beach, water views, close to Portland, and everything in the apartment worked really well. There has been a lot of attention paid as to what would make a guest's stay really awesome. "
United States
David F.
The price is HK$2,129
HK$4,557 total
includes taxes & fees
2 Nov - 3 Nov
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower
Beautiful 1st Floor Apartment & Amazing Shower
9.0 out of 10, Wonderful, (24)
"My brother in law and I stayed here while my husband was hospitalized at the Maine Med and it was a lovely property. Everything was clean and organized, check in was easy and the hosts were responsive and kind. I would stay here again!"
United States
Lillian L.
The price is HK$633
HK$1,325 total
includes taxes & fees
23 Nov - 24 Nov
Beautiful 1st Floor Apartment & Amazing Shower
Exterior detail
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
8.0 out of 10, Very good, (24)
"Property was just as expected. It was nice for us. Only complaint was the grill was broken and we didn’t realize it until after we went and purchased meats for the grill"
United States
Michelle
The price is HK$971
HK$1,931 total
includes taxes & fees
29 Oct - 30 Oct
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Interior
Adorable Portland getaway on the Eastern Promenade
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (123)
"So clean! Loved all the little notes, very helpful. Such a great location close to the water and would definitely recommend this place in the future."
United States
Lorena
The price is HK$863
HK$1,610 total
includes taxes & fees
3 Nov - 4 Nov
Adorable Portland getaway on the Eastern Promenade
Interior
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
10.0 out of 10, Exceptional, (3)
"Wonderful property with great ocean views! The house was very nice, comfortable and quiet. Found the bed to be very comfortable. Would highly recommend to anyone that is interested in staying in this area."
United States
James S.
The price is HK$1,405
HK$4,371 total
includes taxes & fees
5 Nov - 6 Nov
Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches
Beach nearby, sun-loungers, beach towels
Beach House ∆ Prime Location ∆ Steps to the Ocean
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (52)
"We loved everything about our stay here. Perfect location right on Old Orchard Beach. The house is perfect for what we needed/wanted. Wish we could have stayed longer. We would definitely come back for a longer stay next time we’re in Maine. "
United States
Chanmaly V.
The price is HK$1,102
HK$3,768 total
includes taxes & fees
6 Nov - 7 Nov
Beach House ∆ Prime Location ∆ Steps to the Ocean
Living area
The Weldon Hotel
The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (85)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is HK$1,434
HK$2,146 total
includes taxes & fees
9 Nov - 10 Nov
The Weldon Hotel
Exterior
Cheerful 1 bedroom cottage only 50ft from beach
Cheerful 1 bedroom cottage only 50ft from beach
10.0 out of 10, Exceptional, (2)
"We loved the area. We loved the cottage feel. We only wished it had bigger fridge and a better cook top. Other then that it was great."
United States
Chris A.
The price is HK$1,158
HK$1,923 total
includes taxes & fees
2 Nov - 3 Nov
Cheerful 1 bedroom cottage only 50ft from beach
Interior
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
9.8 out of 10, Exceptional, (30)
"Great location and beautiful beach!"
United States
Susan M.
The price is HK$1,547
HK$3,456 total
includes taxes & fees
2 Nov - 3 Nov
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Beach nearby
Escape to the Beach! Cozy Condo in downtown OOB.
Escape to the Beach! Cozy Condo in downtown OOB.
9.6 out of 10, Exceptional, (26)
"Cute place that was perfect for a couple! very clean and right near the beach and pier, would definitely come back again!"
United States
Kaitlyn F.
The price is HK$1,088
HK$2,075 total
includes taxes & fees
5 Nov - 6 Nov
Escape to the Beach! Cozy Condo in downtown OOB.
Living area
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
9.4 out of 10, Exceptional, (13)
"The property was in a good location from everything available in the beach area and the house had enough space to accommodate all 12 of us."
United States
Wayne R.
The price is HK$1,151
HK$3,838 total
includes taxes & fees
27 Oct - 28 Oct
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
1 bedroom, in-room safe, desk, iron/ironing board
Sunny Cottage
Sunny Cottage
10.0 out of 10, Exceptional, (50)
"A great place that has everything you need, including two very accommodating hosts! Would recommend!"
United States
Paul S.
Sunny Cottage
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

Home2 Suites by Hilton Portland Airport

Home2 Suites by Hilton Portland Airport

10/10 Excellent
"Easy location "
James 1-night trip
Posted 2 days ago
Home2 Suites by Hilton 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 Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This holiday home rental outside of South Portland is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in South Portland?

With 28 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 Bug Light and Maine Mall.

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.