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55 South Portland Cottage Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare South Portland cottage rentals from 7 rental sites including HomeAway, Expedia, Booking.com and more, from $46 a night.

20 Second Walk to Willard Beach!

  • 2
  • 2
$275
HomeAway
$275
VRBO
Listed on 4 Sites

Sunset Cottage, Family-Friendly Oasis

  • 3
  • 1
$210
HomeAway
$210
VRBO
Listed on 4 Sites

Classic Island Cottage 20 Minutes By Ferry From Portland

  • 3
  • 1
$185
HomeAway
$185
VRBO
Listed on 4 Sites

The Birdhouse at Willard Beach ~ a Maine cottage at the beach

  • 3
  • 2
$235
HomeAway
$235
VRBO
Listed on 4 Sites

The Woodbury Cottage: An Oceanfront Maine Island Escape

  • 3
  • 2
$428
HomeAway
$428
VRBO
Listed on 4 Sites

Vintage/Modern Urban Cottage in Portland, Maine

  • 2
  • 2
$325
HomeAway
$325
VRBO
Listed on 4 Sites

Perfect Vacation Cottage, Filled with Sunshine and Laughter

  • 3
  • 2
$171
HomeAway
$171
VRBO
Listed on 4 Sites

Charming Peaks Island Cottage

  • 1
  • 1
$119
HomeAway
$119
VRBO
Listed on 4 Sites

Cagasa Cottage: Oceanview, Handicap Friendly, on Seashore Ave

  • 3
  • 2
$280
HomeAway
$280
VRBO
Listed on 4 Sites

Ocean views, quaint cottage, 3BR 2B, wifi, sleeps 8, seats 10, quiet cul-de-sac

  • 3
  • 2
$215
HomeAway
$215
VRBO
Listed on 4 Sites

Cape Elizabeth Rocky Beach Front Cottage

  • 2
  • 1
$295
HomeAway
$295
VRBO
Listed on 4 Sites

Cozy 2 Bedroom Cottage Near Beach

  • 2
  • 2
$314
HomeAway
$314
VRBO
Listed on 4 Sites

Charming Beach Bungalow - Willard Beach

  • 2
  • 2
$175
HomeAway
$175
VRBO
Listed on 4 Sites

Fabulous Turn Of The Century Cottage (with conveniences)

  • 4
  • 2
$450
HomeAway
$450
VRBO
Listed on 4 Sites

Steps From Willard Beach

  • 3
  • 2
$242
HomeAway
$242
VRBO
Listed on 4 Sites

Dog Ocean Side Carriage House

  • 1
  • 1
$210
HomeAway
$210
VRBO
Listed on 4 Sites

Peaks Island Cottage/ The Snuggle Inn

  • 1
  • 1
$150
HomeAway
$150
VRBO
Listed on 4 Sites

Perfect Maine Cottage with spectacular ocean and lighthouse views

  • 3
  • 3
$607
HomeAway
$607
VRBO
Listed on 4 Sites

Charming 3 Bedrm Island Cottage, Near Playground, Pet Friendly

  • 3
  • 1
$200
HomeAway
$200
VRBO
Listed on 4 Sites

Wake up with the water at your doorstep!!!

  • 4
  • 3
$575
HomeAway
$575
VRBO
Listed on 4 Sites

Diamond Cove Cottage / Great Diamond Island Maine

  • 3
  • 2
$300
HomeAway
$300
VRBO
Listed on 4 Sites

Belle Isle Cottage, Vacation Home, Sleeps Six, Family & Pet Friendly!

  • 3
  • 2
$200
HomeAway
$200
VRBO
Listed on 4 Sites

Peaks Island Victorian Cottage

  • 3
  • 2
$242
HomeAway
$242
VRBO
Listed on 4 Sites

Classic Family Cottage, Gorgeous View from Porch, Peaceful Location

  • 6
  • 3
$300
HomeAway
$300
VRBO
Listed on 4 Sites

Oceanfront Cottage with Spectacular Views of Casco Bay

  • 3
  • 2
$428
HomeAway
$428
VRBO
Listed on 4 Sites

3 BR Vacation Home, Convenient Location & Beautiful Ocean Views

  • 3
  • 2
$500
HomeAway
$500
VRBO
Listed on 4 Sites

Beach and Sunsets

  • 3
  • 2
$278
HomeAway
$278
VRBO
Listed on 4 Sites

Great Ocean View Summer Cottage Rental on Great Diamond Island

  • 4
  • 1
$285
HomeAway
$285
VRBO
Listed on 4 Sites

Classic Turn of the Century Island Summer Cottage

  • 5
  • 3
$292
HomeAway
$292
VRBO
Listed on 4 Sites

The Treehouse - Charming Pet-Friendly Peaks Island Maine Cottage

  • 2
  • 3
$250
HomeAway
$250
VRBO
Listed on 4 Sites

Sunny Home on Willard Sq, Dog Friendly, Willard Beach SOPO (new owner)

  • 2
  • 1
$165
HomeAway
$165
VRBO
Listed on 4 Sites

Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch

  • 4
  • 3
$400
HomeAway
$400
VRBO
Listed on 4 Sites

Willard Beach Cottage for up to 8 Guests

  • 3
  • 2
$300
HomeAway
$300
VRBO
Listed on 4 Sites

Historic Island Cottage, 5BR

  • 5
  • 3
$285
HomeAway
$285
VRBO
Listed on 4 Sites

Peaks Island Cottage with beautiful view of Whitehead passage

  • 3
  • 2
$425
HomeAway
$425
VRBO
Listed on 4 Sites

Magical Rambling 5 Bedroom Cottage Built 1904 By John Calvin Stevens

  • 5
  • 2
$500
HomeAway
$500
VRBO
Listed on 4 Sites

South Portland Information

Other Rentals in South Portland

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Canada (EN)
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