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Holiday Rentals in Portland

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
335 rentals in Portland.
Portland Apartment With AMAZING View of Harbor!, holiday rental in Portland
Portland Apartment With AMAZING View of Harbor!, holiday rental in Portland
Portland Apartment With AMAZING View of Harbor!, holiday rental in Portland

Portland Apartment With AMAZING View of Harbor!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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“Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port, holiday rental in Portland
“Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port, holiday rental in Portland
“Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port, holiday rental in Portland

“Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Glorious getaway on Portland's Eastern Promenade., holiday rental in Portland
Glorious getaway on Portland's Eastern Promenade., holiday rental in Portland
Glorious getaway on Portland's Eastern Promenade., holiday rental in Portland

Glorious getaway on Portland's Eastern Promenade.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Cozy Portland Apartment - central to everything!, holiday rental in Portland
Cozy Portland Apartment - central to everything!, holiday rental in Portland
Cozy Portland Apartment - central to everything!, holiday rental in Portland

Cozy Portland Apartment - central to everything!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!, holiday rental in Portland
“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!, holiday rental in Portland
“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!, holiday rental in Portland

“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Morrill Mansion Inn | 8 | Self Check In | Parking, holiday rental in Portland
Morrill Mansion Inn | 8 | Self Check In | Parking, holiday rental in Portland
Morrill Mansion Inn | 8 | Self Check In | Parking, holiday rental in Portland

Morrill Mansion Inn | 8 | Self Check In | Parking

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Check-out
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Morrill Mansion | 2 | Self Check In | Parking, holiday rental in Portland
Morrill Mansion | 2 | Self Check In | Parking, holiday rental in Portland
Morrill Mansion | 2 | Self Check In | Parking, holiday rental in Portland

Morrill Mansion | 2 | Self Check In | Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Check-out
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“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants, holiday rental in Portland
“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants, holiday rental in Portland
“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants, holiday rental in Portland

“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Check-out
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Inn at Parkspring 1 | Self Check In | Parking, holiday rental in Portland
Inn at Parkspring 1 | Self Check In | Parking, holiday rental in Portland
Inn at Parkspring 1 | Self Check In | Parking, holiday rental in Portland

Inn at Parkspring 1 | Self Check In | Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Walk to Old Port ♦ West End Condo ♦ Parking, holiday rental in Portland
Walk to Old Port ♦ West End Condo ♦ Parking, holiday rental in Portland
Walk to Old Port ♦ West End Condo ♦ Parking, holiday rental in Portland

Walk to Old Port ♦ West End Condo ♦ Parking

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Sunny Modern Oasis in Portland’s Trendy East End, holiday rental in Portland
Sunny Modern Oasis in Portland’s Trendy East End, holiday rental in Portland
Sunny Modern Oasis in Portland’s Trendy East End, holiday rental in Portland

Sunny Modern Oasis in Portland’s Trendy East End

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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City Amenities, Casco Bay Sunrises and Natural Beauty, holiday rental in Portland
City Amenities, Casco Bay Sunrises and Natural Beauty, holiday rental in Portland
City Amenities, Casco Bay Sunrises and Natural Beauty, holiday rental in Portland

City Amenities, Casco Bay Sunrises and Natural Beauty

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Check-out
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The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries, holiday rental in Portland
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries, holiday rental in Portland
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries, holiday rental in Portland

The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Check-out
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5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!, holiday rental in Portland
5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!, holiday rental in Portland
5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!, holiday rental in Portland

5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Remodeled Historic Apartment 5 mins from Downtown w/Life Changing Shower!, holiday rental in Portland
Remodeled Historic Apartment 5 mins from Downtown w/Life Changing Shower!, holiday rental in Portland
Remodeled Historic Apartment 5 mins from Downtown w/Life Changing Shower!, holiday rental in Portland

Remodeled Historic Apartment 5 mins from Downtown w/Life Changing Shower!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Adorable Portland getaway on the Eastern Promenade, holiday rental in Portland
Adorable Portland getaway on the Eastern Promenade, holiday rental in Portland
Adorable Portland getaway on the Eastern Promenade, holiday rental in Portland

Adorable Portland getaway on the Eastern Promenade

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Check-out
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Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure., holiday rental in Portland
Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure., holiday rental in Portland
Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure., holiday rental in Portland

Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Check-out
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Historic West End Neighborhood, holiday rental in Portland
Historic West End Neighborhood, holiday rental in Portland
Historic West End Neighborhood, holiday rental in Portland

Historic West End Neighborhood

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Check-out
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Morrill Mansion Inn | 6 | Self Check In | Parking, holiday rental in Portland
Morrill Mansion Inn | 6 | Self Check In | Parking, holiday rental in Portland
Morrill Mansion Inn | 6 | Self Check In | Parking, holiday rental in Portland

Morrill Mansion Inn | 6 | Self Check In | Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
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Cozy, Elegant and Bright 2 bed in the East End, holiday rental in Portland
Cozy, Elegant and Bright 2 bed in the East End, holiday rental in Portland
Cozy, Elegant and Bright 2 bed in the East End, holiday rental in Portland

Cozy, Elegant and Bright 2 bed in the East End

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Charming 2-bedroom steps from the Eastern Promenade, holiday rental in Portland
Charming 2-bedroom steps from the Eastern Promenade, holiday rental in Portland
Charming 2-bedroom steps from the Eastern Promenade, holiday rental in Portland

Charming 2-bedroom steps from the Eastern Promenade

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Check-out
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Chic One Bedroom Apartment In Portland's Arts District, holiday rental in Portland
Chic One Bedroom Apartment In Portland's Arts District, holiday rental in Portland
Chic One Bedroom Apartment In Portland's Arts District, holiday rental in Portland

Chic One Bedroom Apartment In Portland's Arts District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Check-out
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2 Bedroom Apartment on Top Floor in Portland's West End, holiday rental in Portland
2 Bedroom Apartment on Top Floor in Portland's West End, holiday rental in Portland
2 Bedroom Apartment on Top Floor in Portland's West End, holiday rental in Portland

2 Bedroom Apartment on Top Floor in Portland's West End

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
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Skolfield Inn | Parking | Self-check-in | Garden 2, holiday rental in Portland
Skolfield Inn | Parking | Self-check-in | Garden 2, holiday rental in Portland
Skolfield Inn | Parking | Self-check-in | Garden 2, holiday rental in Portland

Skolfield Inn | Parking | Self-check-in | Garden 2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
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Charming Peaks Island Cottage, holiday rental in Portland
Charming Peaks Island Cottage, holiday rental in Portland
Charming Peaks Island Cottage, holiday rental in Portland

Charming Peaks Island Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Check-out
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Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants, holiday rental in Portland
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants, holiday rental in Portland
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants, holiday rental in Portland

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Check-out
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The perfect refinement of vintage seduction, holiday rental in Portland
The perfect refinement of vintage seduction, holiday rental in Portland
The perfect refinement of vintage seduction, holiday rental in Portland

The perfect refinement of vintage seduction

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Check-out
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Inn at Parkspring 4 | Self Check In | Parking, holiday rental in Portland
Inn at Parkspring 4 | Self Check In | Parking, holiday rental in Portland
Inn at Parkspring 4 | Self Check In | Parking, holiday rental in Portland

Inn at Parkspring 4 | Self Check In | Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Check-out
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NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available., holiday rental in Portland
NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available., holiday rental in Portland
NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available., holiday rental in Portland

NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Check-out
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Brand New 2 Bedroom Apartment in Heart of West End, holiday rental in Portland
Brand New 2 Bedroom Apartment in Heart of West End, holiday rental in Portland
Brand New 2 Bedroom Apartment in Heart of West End, holiday rental in Portland

Brand New 2 Bedroom Apartment in Heart of West End

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Check-out
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Elegant condo - walk to Portland's best restaurants & Old Port, holiday rental in Portland
Elegant condo - walk to Portland's best restaurants & Old Port, holiday rental in Portland
Elegant condo - walk to Portland's best restaurants & Old Port, holiday rental in Portland

Elegant condo - walk to Portland's best restaurants & Old Port

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
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Rent a room in the gorgeous Holt House, holiday rental in Portland
Rent a room in the gorgeous Holt House, holiday rental in Portland
Rent a room in the gorgeous Holt House, holiday rental in Portland

Rent a room in the gorgeous Holt House

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Check-out
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Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, holiday rental in Portland
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, holiday rental in Portland
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, holiday rental in Portland

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
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Check-out
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Classic Island Cottage, holiday rental in Portland
Classic Island Cottage, holiday rental in Portland
Classic Island Cottage, holiday rental in Portland

Classic Island Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Check-out
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Modern loft - Downtown, steps from all the action!, holiday rental in Portland
Modern loft - Downtown, steps from all the action!, holiday rental in Portland
Modern loft - Downtown, steps from all the action!, holiday rental in Portland

Modern loft - Downtown, steps from all the action!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Bright and Fresh Back Cove4 Bedroom, Sleeps 8, Perfect for Reunions and Family, holiday rental in Portland
Bright and Fresh Back Cove4 Bedroom, Sleeps 8, Perfect for Reunions and Family, holiday rental in Portland
Bright and Fresh Back Cove4 Bedroom, Sleeps 8, Perfect for Reunions and Family, holiday rental in Portland

Bright and Fresh Back Cove4 Bedroom, Sleeps 8, Perfect for Reunions and Family

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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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, holiday rental in Portland
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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Incredible Location!! Heart of the Old Port/Spacious Townhouse Condo!, holiday rental in Portland
Incredible Location!! Heart of the Old Port/Spacious Townhouse Condo!, holiday rental in Portland
Incredible Location!! Heart of the Old Port/Spacious Townhouse Condo!, holiday rental in Portland

Incredible Location!! Heart of the Old Port/Spacious Townhouse Condo!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Check-out
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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, holiday rental in Portland
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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
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Morrill Mansion | 3 | Self Check In | Parking, holiday rental in Portland
Morrill Mansion | 3 | Self Check In | Parking, holiday rental in Portland
Morrill Mansion | 3 | Self Check In | Parking, holiday rental in Portland

Morrill Mansion | 3 | Self Check In | Parking

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Charming, Secluded, Island Getaway!, holiday rental in Portland
Charming, Secluded, Island Getaway!, holiday rental in Portland
Charming, Secluded, Island Getaway!, holiday rental in Portland

Charming, Secluded, Island Getaway!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Check-out
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Ocean view Victorian, holiday rental in Portland
Ocean view Victorian, holiday rental in Portland
Ocean view Victorian, holiday rental in Portland

Ocean view Victorian

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Check-out
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Rent a room in the gorgeous Holt House, holiday rental in Portland
Rent a room in the gorgeous Holt House, holiday rental in Portland
Rent a room in the gorgeous Holt House, holiday rental in Portland

Rent a room in the gorgeous Holt House

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
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Morrill Mansion Inn | 4 | Self Check In | Parking, holiday rental in Portland
Morrill Mansion Inn | 4 | Self Check In | Parking, holiday rental in Portland
Morrill Mansion Inn | 4 | Self Check In | Parking, holiday rental in Portland

Morrill Mansion Inn | 4 | Self Check In | Parking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
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Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!, holiday rental in Portland
Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!, holiday rental in Portland
Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!, holiday rental in Portland

Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
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Downtown Portand-762 Congress St. Apartment, holiday rental in Portland
Downtown Portand-762 Congress St. Apartment, holiday rental in Portland
Downtown Portand-762 Congress St. Apartment, holiday rental in Portland

Downtown Portand-762 Congress St. Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Check-out
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Back Cove Charmer Close to Everything, holiday rental in Portland
Back Cove Charmer Close to Everything, holiday rental in Portland
Back Cove Charmer Close to Everything, holiday rental in Portland

Back Cove Charmer Close to Everything

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
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Vintage Maine & Modern Convenience in Portlands Exclusive East End, holiday rental in Portland
Vintage Maine & Modern Convenience in Portlands Exclusive East End, holiday rental in Portland
Vintage Maine & Modern Convenience in Portlands Exclusive East End, holiday rental in Portland

Vintage Maine & Modern Convenience in Portlands Exclusive East End

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Brand New 1 Bedroom Apartment in Portland, holiday rental in Portland
Brand New 1 Bedroom Apartment in Portland, holiday rental in Portland
Brand New 1 Bedroom Apartment in Portland, holiday rental in Portland

Brand New 1 Bedroom Apartment in Portland

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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Enjoy Portland With Family or Friends, holiday rental in Portland
Enjoy Portland With Family or Friends, holiday rental in Portland
Enjoy Portland With Family or Friends, holiday rental in Portland

Enjoy Portland With Family or Friends

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Check-out
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Showing results 1-50 of 335
Frequently Asked Questions about Portland