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South Portland Vacation Rentals

1 - 21 of 21 rentals
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Willard Square Getaway - South Portland, ME Vacation Rental
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Willard Square Overlook - South Portland, ME Vacation Rental
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Willard Retreat - South Portland, ME Vacation Rental

Willard Retreat

South Portland, ME
2 Bed 1 Bath Sleeps 6
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The Ocean Street Barn House - South Portland, ME Vacation Rental
99 99 - 85 125 - - - - - - - - - - - -
The Beach House - Old Orchard Beach, ME Vacation Rental

The Beach House

Old Orchard Beach, ME
4 Bed 1.5 Bath Sleeps 10
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Lady Pepperell - Windham, ME Vacation Rental

Lady Pepperell

Windham, ME
3 Bed 1 Bath Sleeps 8
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The Post Road Cottage - Wells, ME Vacation Rental

The Post Road Cottage

Wells, ME
1 Bed 1 Bath Sleeps 4
- - - - 75 75 75 75 99 99 75 75 75 75 75 99 99
Cozy Wells Oasis - Wells, ME Vacation Rental

Cozy Wells Oasis

Wells, ME
0 Bed 1 Bath Sleeps 4
70 90 90 70 75 75 75 75 99 99 75 75 75 75 75 99 99
Harpswell Bay House - Harpswell, ME Vacation Rental

Harpswell Bay House

Harpswell, ME
3 Bed 1 Bath Sleeps 6
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Genes Lodge - Windham, ME Vacation Rental

Genes Lodge

Windham, ME
5 Bed 3 Bath Sleeps 12
- - - 140 140 140 140 140 150 150 140 140 140 140 140 150 150
Selah Lakefront Retreat - Standish, ME Vacation Rental

Selah Lakefront Retreat

Standish, ME
4 Bed 3.5 Bath Sleeps 10
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Grand Avenue Escape - Old Orchard Beach, ME Vacation Rental
- - - - 130 135 135 135 180 180 135 135 135 135 135 180 180
Woodland - Portland, ME Vacation Rental

Woodland

Portland, ME
3 Bed 1.5 Bath Sleeps 8
90 - - - - - - - - - 99 115 115 115 99 - -
The Dunegrass Cottage - Old Orchard Beach, ME Vacation Rental
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It's Jest A Camp - Windham, ME Vacation Rental

It's Jest A Camp

Windham, ME
1 Bed 1 Bath Sleeps 6
- - - 85 90 90 90 90 115 115 90 90 90 90 90 115 115
The Oar House - Wiscasset, ME Vacation Rental

The Oar House

Wiscasset, ME
2 Bed 1 Bath Sleeps 4
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The Shore Road Escape - Cape Elizabeth, ME Vacation Rental
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The Artist Shack - Wells, ME Vacation Rental

The Artist Shack

Wells, ME
1 Bed 1 Bath Sleeps 4
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New Marblehead Lodge - Windham, ME Vacation Rental

New Marblehead Lodge

Windham, ME
3 Bed 1 Bath Sleeps 8
- - - 99 115 115 115 115 145 145 115 115 115 99 - - -
Cozy Wells Getaway - Wells, ME Vacation Rental

Cozy Wells Getaway

Wells, ME
0 Bed 1 Bath Sleeps 4
- - - - 70 70 70 70 99 99 70 70 70 70 70 99 99
Drakes Island Luxury Ocean Retreat - Wells, ME Vacation Rental
195 235 235 195 360 360 360 360 450 450 360 360 360 360 360 450 450

About South Portland

South Portland rated 4.9 out of 5 based on 39 reviews South portland, ME

For a relaxing getaway to a lovely waterfront town, look no further than our South Portland vacation rentals. Situated on Portland Harbor with views of Casco Bay, South Portland is home to both the largest full-service marina and the largest shopping mall in the state of Maine. South Portland is also known for its many gorgeous parks and walking trails, making it a green paradise for visitors from all around. 

First settled by Europeans in 1630, South Portland once boasted farms as far as the eye can see. During the Second World War it became a shipbuilding mecca, supplying cargo ships for England. While South Portland has never officially been a part of Portland, Maine proper, the larger town's skyline is visible from many vantage points in the area.

South Portland Lighthouses 

The waterfront is the premier spot in town, with picture-perfect views as well as several historic attractions. Head to Fort Preble, a stone and earthwork military fort built in 1808. It saw combat during the Civil War through the two World Wars. Stroll down the pier to the Spring Point Ledge Light. Built in 1897, it's the only caisson-style lighthouse in the United States that is accessible via a walkway. Visit the Portland Harbor Museum next door for its displays of maritime history. The Portland Breakwater Lighthouse, aka Bug Light, built in 1875, features cast iron plates and gorgeous Corinthian columns. 

South Portland Historic Attractions

The Maine Military Museum showcases the service of military vets - specifically POWs - via artifacts and exhibits. The Liberty Ship Memorial features the SS Jeremiah O'Brien - one of the liberty ships that defended the United States during the Second World War - and preserves the sacrifices by the men and women who built the ships.  

South Portland's Great Outdoors

The city affords guests more than 500 acres of parks and green spaces. Part of the 3,000-mile-long East Coast Greenway, the Greenbelt Walkway trail extends nearly six miles from Bug Light Park to the 140-acre Wainwright Athletic Complex. Clark's Pond Trail, a 1.1 mile-long woodland trail, winds its way through historic sections of town. Long Creek Trail boasts the spot at which Native Americans and English settlers established a treaty. Other notable trails include Red Brook Tail, Thomas Knight Park, Hinckley Park Loop, Spring Point Shoreway and West End Trails, all offering scenic walkways and bike paths through lovely woodlands and ponds. 

During the summer, locals and visitors alike venture to Willard Beach, a four-acre sand and pebble beach, for fun in the sun. 

Day Trips from South Portland

South Portland is a great base from which to explore all of Maine. Drive 60 miles up the coast and you'll hit the beautiful seaside towns of Lincoln County including Boothbay Harbor, East Boothbay, Wiscasset, and Nobleboro. All offer historic sights and many natural wonders, from hiking trails to lighthouses galore. And of course, more dining and sightseeing opportunities await just to the north in Portland, Maine. 

Scenic views, tranquil trails, and a historic past await you at any of our South Portland vacation rentals! Plan your next getaway today. 

Photo credit: Daniel Zuckerkandel via Shutterstock

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