South Portland Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for South Portland holiday rentals

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)
"Super Cute little apartment! My only complaint, is the parking. It gets a little tight. And the bed is a little firm for my liking, but overall it was super nice and convenient!"
United States
Samantha
The price is HK$762
HK$1,654 total
includes taxes & fees
14 Dec - 15 Dec
Peaceful & minutes from the Old Port with private parking
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$755
HK$1,569 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sunny Spot with Private Parking.
Interior
The Coastal Connection

Apartment in Thorton Heights

The Coastal Connection
2.0 star property
The price is HK$798
HK$2,388 total
includes taxes & fees
14 Dec - 15 Dec
The Coastal Connection
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$958
HK$2,494 total
includes taxes & fees
16 Dec - 17 Dec
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$1,945
HK$3,452 total
includes taxes & fees
13 Dec - 14 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$1,533
HK$3,714 total
includes taxes & fees
14 Dec - 15 Dec
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
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$4,888 total
includes taxes & fees
13 Dec - 14 Dec
Willard Square Family Home
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$1,945
HK$5,334 total
includes taxes & fees
5 Jan - 6 Jan 2026
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
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$1,960
HK$4,325 total
includes taxes & fees
14 Dec - 15 Dec
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
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$677
HK$1,374 total
includes taxes & fees
14 Dec - 15 Dec
Adorable Portland getaway on the Eastern Promenade
Fridge, microwave, stovetop, coffee/tea maker
The Outlet Studio, Rustic Comfort w Fireplace

Holiday Home in Freeport

The Outlet Studio, Rustic Comfort w Fireplace
10.0 out of 10, Exceptional, (11)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The price is HK$630
HK$1,238 total
includes taxes & fees
15 Dec - 16 Dec
The Outlet Studio, Rustic Comfort w Fireplace
Exterior
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$809
HK$1,713 total
includes taxes & fees
14 Dec - 15 Dec
Modern, Luxurious Cabin in the Woods - 03
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$1,687 total
includes taxes & fees
15 Dec - 16 Dec
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
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)
"Sweet place! "
United States
Lisa G.
The price is HK$622
HK$1,552 total
includes taxes & fees
14 Dec - 15 Dec
Pine Point Beach private, quaint, charming studio.
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$539
HK$1,224 total
includes taxes & fees
14 Dec - 15 Dec
Beautiful 1st Floor Apartment & Amazing Shower
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$1,543 total
includes taxes & fees
4 Jan - 5 Jan 2026
Adorable 1 bedroom cabin only 50 ft from beach#1
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)
"Super cute spot! Wonderful girls weekend!"
United States
Diana M.
The price is HK$887
HK$1,857 total
includes taxes & fees
11 Jan - 12 Jan 2026
West End Bright Spot with Parking.
Interior
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

Apartment in Downtown Saco

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
10.0 out of 10, Exceptional, (15)
"The property was exactly as advertised, and it was a perfect two night stay for us on a road trip up the Maine coast with our dogs. The location was perfect to explore Portland, Saco, Biddeford, and Kennebunkport. The hosts were super responsive and friendly. We would definitely stay here again in future!"
United States
Ryan S.
The price is HK$825
HK$2,137 total
includes taxes & fees
14 Dec - 15 Dec
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
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$1,586 total
includes taxes & fees
5 Jan - 6 Jan 2026
Escape to the Beach! Cozy Condo in downtown OOB.
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)
"It was clean and neat and just steps to the beach. It had everything you could possibly need."
United States
Mare E.
The price is HK$1,103
HK$3,746 total
includes taxes & fees
13 Dec - 14 Dec
Beach House ∆ Prime Location ∆ Steps to the Ocean
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Portland Hotel Reviews

Home2 Suites by Hilton Portland Airport

Home2 Suites by Hilton Portland Airport

10/10 Excellent
"Very clean "
Anne 1-night trip
Posted 3 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?

Quintessential Maine Beach Cottage: This holiday home rental outside of South Portland is located on the beach, and has a private garden, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in South Portland?

With 30 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.