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South Portland Vacation Rentals

1 - 42 of 48 rentals
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The East Ender - Portland, ME Vacation Rental

The East Ender

Portland, ME
2 Bed 1 Bath Sleeps 4
191 200 - - - - - - - - 261 - - 268 259 - -
 Knotty Dream - Scarborough, ME Vacation Rental

Knotty Dream

Scarborough, ME
0 Bed 1 Bath Sleeps 2
129 129 - - - - - - - - - - - - - - -
Paradise Cove - Wells, ME Vacation Rental

Paradise Cove

Wells, ME
1 Bed 2 Bath Sleeps 6 (4 Adults Max)
66 - - - - - - - - - 129 - - - - 150 176
Hackett Road Hangout - Windham, ME Vacation Rental

Hackett Road Hangout

Windham, ME
3 Bed 2.5 Bath Sleeps 9
186 201 286 297 311 300 302 303 303 343 369 - - - - - -
Old Port Charmer - Portland, ME Vacation Rental

Old Port Charmer

Portland, ME
3 Bed 1 Bath Sleeps 6
210 220 - - 255 258 250 251 248 - - - 295 295 - - -
The Dunegrass Cottage - Old Orchard Beach, ME Vacation Rental
- - - - 272 288 272 - - - 338 418 440 441 441 417 -
The Artist Shack - Wells, ME Vacation Rental

The Artist Shack

Wells, ME
1 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - 172
Ocean Breezes - Wells, ME Vacation Rental

Ocean Breezes

Wells, ME
0 Bed 1 Bath Sleeps 4
69 76 92 - - - - 95 102 110 - - 106 107 - - -
Wellington Manor 224 - Wells, ME Vacation Rental

Wellington Manor 224

Wells, ME
0 Bed 1 Bath Sleeps 4
59 66 - - - 85 107 102 98 - - 125 128 128 129 120 -
Summer Sands Studio - Wells, ME Vacation Rental

Summer Sands Studio

Wells, ME
0 Bed 1 Bath Sleeps 4
63 66 - - - - 90 - - 126 132 137 125 - - - 113
 Little Sebago Landing  - Gray, ME Vacation Rental

Little Sebago Landing

Gray, ME
4 Bed 2.5 Bath Sleeps 7
- 139 - - 184 207 195 195 193 207 250 253 256 256 256 256 276
Two-Bedroom House Steps to Wells Beach  - Wells, ME Vacation Rental
- 86 - - 140 - - - - 194 - - - - - - -
 Cove View - Wells, ME Vacation Rental

Cove View

Wells, ME
3 Bed 3 Bath Sleeps 10
- - - - - 204 269 239 - - - - - - - - -
Meme's Ocean Haven - Old Orchard Beach, ME Vacation Rental

Meme's Ocean Haven

Old Orchard Beach, ME
2 Bed 1.5 Bath Sleeps 5
- - - - 188 199 188 - - - - 232 - - - - -
Wellington Manor 126 - Wells, ME Vacation Rental

Wellington Manor 126

Wells, ME
0 Bed 1 Bath Sleeps 4
63 66 - - - - - 108 115 139 139 147 142 143 136 - -
The Eastern Avenue Cottage - Wells, ME Vacation Rental

The Eastern Avenue Cottage

Wells, ME
2 Bed 1 Bath Sleeps 5
- - - - - - - - - - - - - - - - -
Post Road Charmer - Wells, ME Vacation Rental

Post Road Charmer

Wells, ME
2 Bed 1 Bath Sleeps 4
- 86 - - - - - 134 136 - - - - 182 193 180 -
Sweet EmOcean - Ogunquit, ME Vacation Rental

Sweet EmOcean

Ogunquit, ME
4 Bed 3 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
The Hoxie House - Old Orchard Beach, ME Vacation Rental

The Hoxie House

Old Orchard Beach, ME
5 Bed 2 Bath Sleeps 10
- - - - - 265 280 265 - - - 346 386 366 - - -
It's Jest A Camp - Windham, ME Vacation Rental

It's Jest A Camp

Windham, ME
1 Bed 1 Bath Sleeps 6
89 - - - 146 149 150 151 143 - - - - - - - -
The Post Road Cottage - Wells, ME Vacation Rental

The Post Road Cottage

Wells, ME
1 Bed 1 Bath Sleeps 4
160 160 - - - 160 160 160 160 - - - - - - 200 -
Calabar Gardens – Mellow Marshlands  - Wells, ME Vacation Rental
- - - 139 160 135 167 157 152 - - - - - - - -
As Good As It Gets - Kennebunkport, ME Vacation Rental

As Good As It Gets

Kennebunkport, ME
3 Bed 2.5 Bath Sleeps 9
- - - - - - - - - - - - - - - - -
School Street Sanctuary - Kennebunkport, ME Vacation Rental
- - - - - - - - - - - - - - - 389 348
Cozy Wells Oasis - Wells, ME Vacation Rental

Cozy Wells Oasis

Wells, ME
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - 131 144
Grand Avenue Escape - Old Orchard Beach, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Surfside - Cape Elizabeth, ME Vacation Rental

Surfside

Cape Elizabeth, ME
2 Bed 1 Bath Sleeps 4
- 150 - - - - - - - - - - - - - - -
Riverbank Place - Ogunquit, ME Vacation Rental

Riverbank Place

Ogunquit, ME
1 Bed 1 Bath Sleeps 4 (2 Adults Max)
77 86 128 128 127 104 - - - - - - 148 157 158 155 161
Sea Marsh Escape  - Wells, ME Vacation Rental

Sea Marsh Escape

Wells, ME
2 Bed 1 Bath Sleeps 4
- - - - - - - - - - 156 190 182 174 - - -
 Cute Cottage Steps to Wells Beach - Wells, ME Vacation Rental
- - - - 103 108 108 108 108 138 - - - - - - -
Grandeur On The Green - Kennebunkport, ME Vacation Rental

Grandeur On The Green

Kennebunkport, ME
5 Bed 3.5 Bath Sleeps 14
410 410 - - 427 424 458 466 481 647 647 920 910 897 915 897 897
Sandy Toes Escape - Wells, ME Vacation Rental

Sandy Toes Escape

Wells, ME
0 Bed 1 Bath Sleeps 4
- - - - - - - - 93 - - - - - - - -
Sea Spray Village Getaway - Wells, ME Vacation Rental

Sea Spray Village Getaway

Wells, ME
2 Bed 1 Bath Sleeps 4
76 - - - - 135 175 165 - - - - - - - - -
The Lighthouse Getaway - Wells, ME Vacation Rental

The Lighthouse Getaway

Wells, ME
0 Bed 1 Bath Sleeps 4
- - - - - - 109 109 111 114 - - - - - - -
Beach Plum Cottage - Ogunquit, ME Vacation Rental

Beach Plum Cottage

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

New Marblehead Lodge

Windham, ME
4 Bed 2 Bath Sleeps 8
- - - 400 400 400 400 400 400 400 432 434 446 442 433 419 430
Lady Pepperell - Windham, ME Vacation Rental

Lady Pepperell

Windham, ME
3 Bed 1 Bath Sleeps 6
- - - - 375 375 375 375 375 375 375 375 375 375 375 375 -
Genes Lodge - Windham, ME Vacation Rental

Genes Lodge

Windham, ME
5 Bed 3 Bath Sleeps 10
- - - 436 436 436 436 436 436 436 479 481 494 490 480 465 -
Harpswell Bay House - Harpswell, ME Vacation Rental

Harpswell Bay House

Harpswell, ME
3 Bed 1 Bath Sleeps 6
- 163 168 - - - - - - - 244 314 317 311 295 - -
Drifting In - Harpswell, ME Vacation Rental

Drifting In

Harpswell, ME
2 Bed 1 Bath Sleeps 4
140 140 - - 140 140 140 140 140 140 141 159 161 154 - - -
Selah Lakefront Retreat - Standish, ME Vacation Rental

Selah Lakefront Retreat

Standish, ME
4 Bed 3.5 Bath Sleeps 10
- 243 - - - - - - - - - - - - - - -
The Perch at Beachwalk - Old Orchard Beach, ME Vacation Rental
- - 97 - - - - - - - - - - - - - -
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About South Portland

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.

Lighthouses in South Portland, ME

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. 

Historic Attractions in South Portland, ME

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, ME

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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