Vacation rentals in South Portland

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Top-rated accommodation in South Portland

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cottage in Scarborough

4.85 out of 5 average rating, 279 reviews

Charming beach cottage

Pine Point is a beautiful sleepy village surrounded on three sides by water: peaceful salt marsh, river to the sea, and ocean, with an 8 mile long white sand beach, extensive sand bars at low tide (great for sand dollars!). It is the perfect spot for an unforgettable family vacation. The beach here is considered by many to be the best walking and activity beach in Maine, as well as spectacularly beautiful. Come experience an idyllic week at the beach in Pine Point. This beach is perfect for many reasons: great swimming, windsurfing, beach combing, extensive sandbars, fishing off the jetty. The cottage is located in a quaint and quiet neighborhood, just steps from the path to the beach. Spend your days reading and sunbathing, and fall asleep at night to the sounds of the ocean just outside your window. The house has an open layout downstairs with a light breezy feel, and cozy upstairs sleeping quarters. Beautiful back yard and great deck in the shade, front porch with hammock for afternoon snoozes, and all the amenities of home. 20 minutes from the great little city of Portland for added excitement.

22 – 29 Apr

$1,312 AUD total
Superhost

Apartment in Portland

4.82 out of 5 average rating, 347 reviews

Spacious and Comfortable Private Apartment

Third floor (i.e. a few stairs) spacious apartment with a private entrance. Walking distance to Thompson’s Point, Maine Med and many other trails and attractions. The Old Port is a 5 minute drive (1.5 mi.). There is plenty of free street parking available. Space heaters warm the space in the winter, and a/c is provided in the summer. The house is shared by first floor tenants while our family occupies the second floor. Again, several stairs to navigate, but quite comfortable once you settle in!

9 – 16 Mar

$865 AUD total
Guest favourite

Apartment in South Portland

4.89 out of 5 average rating, 199 reviews

Willard Square - The View

“So much bigger than in the photos.” A charming apartment in the Willard Beach neighborhood of South Portland, Maine. There are bakeries, ice-cream parlor and restaurants within walking distance. Easy access to Portland , Midcoast airport. The area has many local craft breweries and award winning restaurants. This apartment is the perfect spot to stay for your Maine vacation. It is a great walking neighborhood with many attractions nearby, but you might want a car for getting around the area. I

10 – 17 Mar

$2,219 AUD total

Popular amenities for South Portland accommodation

Stay near South Portland's top sights

The Maine Mall86 locals recommend
Portland International Jetport50 locals recommend
Fort Williams Park229 locals recommend
Thompson Point28 locals recommend
Portland Museum of Art412 locals recommend
Portland Harbor Museum347 locals recommend

Other great accommodation in South Portland

Guest favourite

Apartment in Portland

4.97 out of 5 average rating, 475 reviews

Amazing Views! Perfect Location. Loft style feel.

4 – 11 Apr

$1,660 AUD total
Guest favourite

Apartment in South Portland

4.91 out of 5 average rating, 148 reviews

Sunny and beautiful brick house apartment

29 Oct – 5 Nov

$2,523 AUD total
Guest favourite

Apartment in South Portland

4.95 out of 5 average rating, 167 reviews

Comfortable apartment near Willard Beach!

29 June – 6 July

$5,216 AUD total
Superhost

Apartment in Portland

4.81 out of 5 average rating, 936 reviews

Parking | Self-check-in | Washer+Dryer | Kitchen 5

12 – 19 Jan

$1,241 AUD total
Guest favourite

Guest suite in Freeport

4.96 out of 5 average rating, 193 reviews

Weather's Edge, Freeport

30 May – 6 June

$1,065 AUD total
Guest favourite

Apartment in South Portland

4.96 out of 5 average rating, 163 reviews

Beautifully renovated spacious 2br apt in SoPo💗💗💗💗

25 Aug – 1 Sept

$2,860 AUD total
Guest favourite

Guest suite in Portland

4.91 out of 5 average rating, 193 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

17 – 24 Feb

$1,290 AUD total
Guest favourite

Guesthouse in Windham

5.0 out of 5 average rating, 214 reviews

Cottage on Black Brook Preserve

30 May – 6 June

$1,564 AUD total
Guest favourite

Condo in South Portland

4.94 out of 5 average rating, 116 reviews

Rustic Willard Beach condo ten mins from Old Port!

15 – 22 Mar

$3,242 AUD total
Guest favourite

Home in Lisbon

4.94 out of 5 average rating, 328 reviews

Unplug at a Beachy Bolthole with Classic New England Style

20 – 27 Feb

$850 AUD total
Guest favourite

Apartment in South Portland

4.95 out of 5 average rating, 255 reviews

Stylish Studio Apt with Parking

26 July – 2 Aug

$2,409 AUD total
Guest favourite

Home in South Portland

4.9 out of 5 average rating, 102 reviews

Cottage style home 2 blocks from the beach!

22 – 29 Nov

$4,575 AUD total

Quick stats about holiday rentals in South Portland

Total rentals

560 properties

Rentals with dedicated workspaces

290 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

160 properties allow pets

Family-friendly rentals

260 properties are a good fit for families

Total number of reviews

56K reviews

Destinations to explore