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South Portland Holiday Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for South Portland holiday rentals

Dining
Sunny Spot with Private Parking.

Apartment in Knightville

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$1,560 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sunny Spot with Private Parking.
Outdoor dining
Peaceful & minutes from the Old Port with private parking

Apartment in Knightville

Peaceful & minutes from the Old Port with private parking
9.8 out of 10, Exceptional, (7)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is HK$762
HK$1,670 total
includes taxes & fees
4 Jan - 5 Jan 2026
Peaceful & minutes from the Old Port with private parking
Beach nearby
Arlie`s Digs! - One Block To Willard Beach!

Condo in Willard Beach

Arlie`s Digs! - One Block To Willard Beach!
10.0 out of 10, Exceptional, (62)
"We had a wonderful week here. Fantastic proximity to the beach & a great bakery and ice cream shop. They accommodated us and our dog very well and had everything we need for a great stay. "
United States
Elizabeth C.
The price is HK$1,033
HK$2,550 total
includes taxes & fees
4 Jan - 5 Jan 2026
Arlie`s Digs! - One Block To Willard Beach!
Fridge, microwave, oven, stovetop
Modern Getaway by the Sea

Holiday Home in South Portland

Modern Getaway by the Sea
10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
The price is HK$1,944
HK$3,451 total
includes taxes & fees
25 Dec - 26 Dec
Modern Getaway by the Sea
On the beach, sun-loungers, beach towels
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2

Apartment in Willard

Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
9.6 out of 10, Exceptional, (4)
"Enjoyed our stay, perfect for 2 kids and parents. Outdoor shower was a great addition for our beach days!"
United States
Greg R.
The price is HK$2,131
HK$4,561 total
includes taxes & fees
6 Jan - 7 Jan 2026
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
Private kitchen
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

Holiday Home in South Portland

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
The price is HK$1,750
HK$5,052 total
includes taxes & fees
6 Jan - 7 Jan 2026
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Property grounds
Willard Square Family Home

Holiday Home in Willard Beach

Willard Square Family Home
9.6 out of 10, Exceptional, (9)
"Thoroughly enjoyed this house! "
United States
David W.
The price is HK$2,489
HK$4,887 total
includes taxes & fees
25 Dec - 26 Dec
Willard Square Family Home
On the beach, sun-loungers, beach towels
Step right out to the beach! Amazing location 7 min to Portland. Unit 4

Apartment in Willard

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$2,302
HK$4,773 total
includes taxes & fees
6 Jan - 7 Jan 2026
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower

Apartment in Parkside

Beautiful 1st Floor Apartment & Amazing Shower
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is HK$548
HK$1,233 total
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful 1st Floor Apartment & Amazing Shower
Interior
Adorable Portland getaway on the Eastern Promenade

Apartment in Munjoy Hill

Adorable Portland getaway on the Eastern Promenade
9.6 out of 10, Exceptional, (127)
"Very convenient location. Comfortable accommodation! I would stay here again. "
United States
Cynthia W.
The price is HK$575
HK$1,263 total
includes taxes & fees
25 Dec - 26 Dec
Adorable Portland getaway on the Eastern Promenade
Exterior detail
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5

Cottage in Old Orchard Beach

Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
8.0 out of 10, Very good, (24)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
The price is HK$778
HK$1,653 total
includes taxes & fees
5 Jan - 6 Jan 2026
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
Beach nearby
Adorable 1 bedroom cabin only 50 ft from beach#1

Cottage in Old Orchard Beach

Adorable 1 bedroom cabin only 50 ft from beach#1
10.0 out of 10, Exceptional, (3)
"The location was wonderful! The host was so communicative and kind!"
United States
Courtney W.
The price is HK$848
HK$1,517 total
includes taxes & fees
6 Jan - 7 Jan 2026
Adorable 1 bedroom cabin only 50 ft from beach#1
Beach nearby, sun-loungers, beach towels
Beach House ∆ Prime Location ∆ Steps to the Ocean

Holiday Home in Old Orchard Beach

Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (55)
"Excellent location for an after Labor Day vacation. Easy access to the beach. Quiet street. Very nice accommodations with plenty of room. "
United States
Charles C.
The price is HK$1,102
HK$3,796 total
includes taxes & fees
30 Dec - 31 Dec
Beach House ∆ Prime Location ∆ Steps to the Ocean
Fridge, microwave, oven, stovetop
Pine Point Beach private, quaint, charming studio.

Apartment in Blue Point

Pine Point Beach private, quaint, charming studio.
2.0 star property
10.0 out of 10, Exceptional, (24)
"Cozy, clean and comfortable! Perfect weekend beach get away! "
United States
jen e.
The price is HK$622
HK$1,551 total
includes taxes & fees
28 Dec - 29 Dec
Pine Point Beach private, quaint, charming studio.
Beach nearby
Escape to the Beach! Cozy Condo in downtown OOB.

Condo in Old Orchard Beach

Escape to the Beach! Cozy Condo in downtown OOB.
9.6 out of 10, Exceptional, (26)
"Easy check-in, super clean, amazing location! "
United States
Chantelle V.
The price is HK$700
HK$1,568 total
includes taxes & fees
6 Jan - 7 Jan 2026
Escape to the Beach! Cozy Condo in downtown OOB.
Exterior detail
West End Bright Spot with Parking.

Apartment in West End

West End Bright Spot with Parking.
10.0 out of 10, Exceptional, (16)
"Great location, clean with everything we needed. Will definitely stay again when in Portland!"
United States
vanessa h.
The price is HK$887
HK$1,848 total
includes taxes & fees
11 Jan - 12 Jan 2026
West End Bright Spot with Parking.
Exterior
Cozy, Elegant and Bright 2 bed in the East End

Condo in Munjoy Hill

Cozy, Elegant and Bright 2 bed in the East End
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
The price is HK$714
HK$1,804 total
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy, Elegant and Bright 2 bed in the East End
Property grounds
Modern, Luxurious Cabin in the Woods - 03

Cabin in Freeport

Modern, Luxurious Cabin in the Woods - 03
10.0 out of 10, Exceptional, (6)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is HK$1,572
HK$2,519 total
includes taxes & fees
4 Jan - 5 Jan 2026
Modern, Luxurious Cabin in the Woods - 03
Beach
Orchid Harbor, Bailey Island 3BR

Holiday Home in Harpswell

Orchid Harbor, Bailey Island 3BR
9.8 out of 10, Exceptional, (8)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
The price is HK$1,764
HK$3,812 total
includes taxes & fees
2 Jan - 3 Jan 2026
Orchid Harbor, Bailey Island 3BR
1 bedroom, WiFi, bed sheets
Studio Apartment near downtown Walkable!

Apartment in West Bayside

Studio Apartment near downtown Walkable!
8.4 out of 10, Very good, (7)
"The summary and the pictures shown are exactly what you’re going to get. The owner did a good job with the description, I "
United States
Alexandria T.
The price is HK$490
HK$1,048 total
includes taxes & fees
29 Dec - 30 Dec
Studio Apartment near downtown Walkable!
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

Long Creek Hotel by IHG

Long Creek Hotel by IHG

10/10 Excellent
"Price was good and clean."
tammi 1-night trip
Posted 14 hours ago
Long Creek Hotel by IHG

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?

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families! : This holiday home rental outside of South Portland is located in the city centre, 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 books.

How many holiday rentals are there in South Portland?

With 31 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.