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South Portland Holiday Rentals

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50 rentals in South Portland.
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Modern Apartment Two Blocks from Willard Beach in South Portland, holiday rental in South Portland

Modern Apartment Two Blocks from Willard Beach in South Portland

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!, holiday rental in South Portland

WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!

3 bedrooms
2 bathrooms
Sleeps 9
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Charming 2BR, Block from sandy beach and friendly Willard Square, holiday rental in South Portland

Charming 2BR, Block from sandy beach and friendly Willard Square

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood, holiday rental in South Portland

Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Willard Beach Get Away - Dog Friendly, holiday rental in South Portland

Willard Beach Get Away - Dog Friendly

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining, holiday rental in South Portland

New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW: Stunningly Renovated Beach House with OCEAN VIEWS-steps to beach.  Pets OK!, holiday rental in South Portland

NEW: Stunningly Renovated Beach House with OCEAN VIEWS-steps to beach. Pets OK!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Glorious getaway on Portland's Eastern Promenade., holiday rental in South Portland

Glorious getaway on Portland's Eastern Promenade.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic West End Neighborhood, holiday rental in South Portland

Historic West End Neighborhood

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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3BR home: East End neighborhood: walk to ocean or downtown, local eateries, holiday rental in South Portland

3BR home: East End neighborhood: walk to ocean or downtown, local eateries

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Cozy Getaway In The City, holiday rental in South Portland

Cozy Getaway In The City

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Charming 2-bedroom steps from the Eastern Promenade, holiday rental in South Portland

Charming 2-bedroom steps from the Eastern Promenade

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Sleek Condo w/ a Private Patio - Less than Two Blocks from the Beach/Park, holiday rental in South Portland

Sleek Condo w/ a Private Patio - Less than Two Blocks from the Beach/Park

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in South Portland

The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Adorable Portland getaway on the Eastern Promenade, holiday rental in South Portland

Adorable Portland getaway on the Eastern Promenade

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Elegant condo w/ gas fireplace - walk to Portland's best restaurants & Old Port!, holiday rental in South Portland

Elegant condo w/ gas fireplace - walk to Portland's best restaurants & Old Port!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Polished, Modern Condo w/ a Balcony - Walk to Eastern Promenade & Casco Bay!, holiday rental in South Portland

Polished, Modern Condo w/ a Balcony - Walk to Eastern Promenade & Casco Bay!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sleek & Newly-Renovated Third-Floor Condo w/ Amazing Water Views - Walk to Bay!, holiday rental in South Portland

Sleek & Newly-Renovated Third-Floor Condo w/ Amazing Water Views - Walk to Bay!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious 5 Bedroom, 2 Full Baths, Walkable Neighborhood, holiday rental in South Portland

Spacious 5 Bedroom, 2 Full Baths, Walkable Neighborhood

5 bedrooms
2 bathrooms
Sleeps 20
Match: Sleeps
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2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood, holiday rental in South Portland

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning White Water Ocean Views From This Peaks Island Home, holiday rental in South Portland

Stunning White Water Ocean Views From This Peaks Island Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Fresh East End Apartment Walkable to Downtown Portland, holiday rental in South Portland

Fresh East End Apartment Walkable to Downtown Portland

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Island Cottage, 5BR, holiday rental in South Portland

Historic Island Cottage, 5BR

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Back Cove Charmer Close to Everything, holiday rental in South Portland

Back Cove Charmer Close to Everything

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Art Filled East End Home a short walk to waterfront, restaurants and shops, holiday rental in South Portland

Art Filled East End Home a short walk to waterfront, restaurants and shops

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Adorable Peaks Island Cottage, holiday rental in South Portland

Adorable Peaks Island Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Portland B&B room - steps from Eastern Prom and beach and close to town too!, holiday rental in South Portland

Portland B&B room - steps from Eastern Prom and beach and close to town too!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cape Elizabeth Beach Camp With Private Beach On Private Road, holiday rental in South Portland

Cape Elizabeth Beach Camp With Private Beach On Private Road

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Bright And Cozy 2 Bedroom Ranch Perfectly Located Near Beaches And Attractions, holiday rental in South Portland

Bright And Cozy 2 Bedroom Ranch Perfectly Located Near Beaches And Attractions

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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7 Minutes to the Old Port!  Steps to the Back Cove / Ocean!  Entire Home, holiday rental in South Portland

7 Minutes to the Old Port! Steps to the Back Cove / Ocean! Entire Home

5 bedrooms
2 bathrooms
Sleeps 20
Match: Sleeps
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Stunning Waterfront House with Hot Tub, holiday rental in South Portland

Stunning Waterfront House with Hot Tub

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Sunset Cottage, Family-Friendly Oasis, holiday rental in South Portland

Sunset Cottage, Family-Friendly Oasis

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Classic, cozy family cottage with modern amenities and ocean view from porch, holiday rental in South Portland

Classic, cozy family cottage with modern amenities and ocean view from porch

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season, holiday rental in South Portland

Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Lovely Cape Elizabeth Family Home 5 miles to Portland! 3,700 sqft custom built!!, holiday rental in South Portland

Lovely Cape Elizabeth Family Home 5 miles to Portland! 3,700 sqft custom built!!

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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BRAND NEW luxury penthouse condo w/ water views right in the heart of Old Port!, holiday rental in South Portland

BRAND NEW luxury penthouse condo w/ water views right in the heart of Old Port!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch, holiday rental in South Portland

Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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1st Floor Private Entrance Condo.  Walk to Restaurants and Parks!, holiday rental in South Portland

1st Floor Private Entrance Condo. Walk to Restaurants and Parks!

4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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WILLARD BEACH:  Stunning newly RENOVATED HOUSE!   4 Mins to DT Portland., holiday rental in South Portland

WILLARD BEACH: Stunning newly RENOVATED HOUSE! 4 Mins to DT Portland.

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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NEW LISTING:  Stunning, fully-renovated home with private beach and HOT TUB!, holiday rental in South Portland

NEW LISTING: Stunning, fully-renovated home with private beach and HOT TUB!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Authentic Coastal Maine Cottage Living, holiday rental in South Portland

Authentic Coastal Maine Cottage Living

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Casco Bay Sunrise Vista, holiday rental in South Portland

Casco Bay Sunrise Vista

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Bold ocean views from your pool at the property and walk down to the rocky, sand, holiday rental in South Portland

Bold ocean views from your pool at the property and walk down to the rocky, sand

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Peaks Island Cottage with beautiful view of Whitehead passage, holiday rental in South Portland

Peaks Island Cottage with beautiful view of Whitehead passage

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Magnificent Seaside Castle , English style Estate with private beach., holiday rental in South Portland

Magnificent Seaside Castle , English style Estate with private beach.

6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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The perfect refinement of vintage seduction, holiday rental in South Portland

The perfect refinement of vintage seduction

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning - modern 2 bedroom Victorian mansion pad, holiday rental in South Portland

Stunning - modern 2 bedroom Victorian mansion pad

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ultra cool new modern flat, holiday rental in South Portland

Ultra cool new modern flat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Victorian architecture dipped in refined modernity, holiday rental in South Portland

Victorian architecture dipped in refined modernity

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nature with in-town living that feels a world away, holiday rental in South Portland

Nature with in-town living that feels a world away

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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