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Portland Holiday Rentals

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37 rentals in Portland.
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Glorious getaway on Portland's Eastern Promenade., holiday rental in Portland

Glorious getaway on Portland's Eastern Promenade.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 2-bedroom steps from the Eastern Promenade, holiday rental in Portland

Charming 2-bedroom steps from the Eastern Promenade

2 bedrooms
1 bathroom
Sleeps 5
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The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Portland

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

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

Cozy Getaway In The City

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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3BR home: East End neighborhood: walk to ocean or downtown, local eateries, holiday rental in 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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Sleek Condo w/ a Private Patio - Less than Two Blocks from the Beach/Park, holiday rental in 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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Historic West End Neighborhood, holiday rental in Portland

Historic West End Neighborhood

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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NEW LISTING ☼ Unique Oceanfront Home, holiday rental in Portland

NEW LISTING ☼ Unique Oceanfront Home

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Adorable Portland getaway on the Eastern Promenade, holiday rental in 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 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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Stunning Waterfront House with Hot Tub, holiday rental in Portland

Stunning Waterfront House with Hot Tub

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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DIRECT OCEANFRONT Perfect location, holiday rental in Portland

DIRECT OCEANFRONT Perfect location

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

Fresh East End Apartment Walkable to Downtown Portland

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Adorable Peaks Island Cottage, holiday rental in Portland

Adorable Peaks Island Cottage

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 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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Stunning White Water Ocean Views From This Peaks Island Home, holiday rental in Portland

Stunning White Water Ocean Views From This Peaks Island Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Evergreen cottage 5' from the water, holiday rental in Portland

Evergreen cottage 5' from the water

5 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Art Filled East End Home a short walk to waterfront, restaurants and shops, holiday rental in 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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Peaks Island Cottage with beautiful view of Whitehead passage, holiday rental in Portland

Peaks Island Cottage with beautiful view of Whitehead passage

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Island Cottage, 5BR, holiday rental in Portland

Historic Island Cottage, 5BR

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious 5 Bedroom, 2 Full Baths, Walkable Neighborhood, holiday rental in 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 Portland

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

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 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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Back Cove Charmer Close to Everything, holiday rental in Portland

Back Cove Charmer Close to Everything

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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7 Minutes to the Old Port!  Steps to the Back Cove / Ocean!  Entire Home, holiday rental in 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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Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season, holiday rental in Portland

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

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Sunset Cottage, Family-Friendly Oasis, holiday rental in Portland

Sunset Cottage, Family-Friendly Oasis

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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BRAND NEW luxury penthouse condo w/ water views right in the heart of Old Port!, holiday rental in 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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Classic, cozy family cottage with modern amenities and ocean view from porch, holiday rental in 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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1st Floor Private Entrance Condo.  Walk to Restaurants and Parks!, holiday rental in Portland

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

4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch, holiday rental in Portland

Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Authentic Coastal Maine Cottage Living, holiday rental in 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 Portland

Casco Bay Sunrise Vista

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Stunning - modern 2 bedroom Victorian mansion pad, holiday rental in Portland

Stunning - modern 2 bedroom Victorian mansion pad

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

Victorian architecture dipped in refined modernity

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ultra cool new modern flat, holiday rental in Portland

Ultra cool new modern flat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The perfect refinement of vintage seduction, holiday rental in Portland

The perfect refinement of vintage seduction

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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