Portland, Maine

Vacation Rentals in Portland, Maine

Discover 294 vacation rental properties in Portland. From 1 to 9 bedrooms. Average $492/night. 100% have pools.

294 verified listings Book securely on VRBO Prices updated March 2026

294 properties available

Downtown Portand-762 Congress St. Apartment

Downtown Portand-762 Congress St. Apartment

1 bed 1 bath
PoolA/CWiFiBalcony
$231/night
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Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.

2 beds 1 bath
PoolA/CWiFiBalcony
$320/night
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Elegant condo - walk to Portland's best restaurants & Old Port

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

1 bed 1 bath
PoolA/CWiFiBalcony
$182/night
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Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$170/night
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“Margaret” Penthouse Suite: Casco Bay views, right in the Old Port. Parking!

“Margaret” Penthouse Suite: Casco Bay views, right in the Old Port. Parking!

2 beds 2 baths
PoolA/CWiFiBalcony
$776/night
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“Percival” Penthouse Suite: Breathtaking Views, Cupola, Parking!

“Percival” Penthouse Suite: Breathtaking Views, Cupola, Parking!

2 beds 2 baths
PoolA/CWiFiBalcony
$687/night
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Cozy, Elegant and Bright 2 bed in the East End

Cozy, Elegant and Bright 2 bed in the East End

2 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries

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

2 beds 1 bath
PoolA/CWiFiBalcony
$403/night
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“Henry” Penthouse Suite: Waterfront, in the heart of the Old Port, Parking!

“Henry” Penthouse Suite: Waterfront, in the heart of the Old Port, Parking!

2 beds 2 baths
PoolA/CWiFiBalcony
$862/night
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City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty

2 beds 1 bath
PoolA/CWiFiBalcony
$276/night
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Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

1 bed 1 bath
PoolA/CWiFiBalcony
$481/night
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Fresh East End Apartment Walkable to Downtown Portland

Fresh East End Apartment Walkable to Downtown Portland

1 bed 1 bath
PoolA/CWiFiBalcony
$376/night
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Back Cove Charmer Close to Everything

Back Cove Charmer Close to Everything

1 bed 1 bath
PoolA/CWiFiBalcony
$216/night
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Luxury Condo Downtown Portland Old Port

Luxury Condo Downtown Portland Old Port

1 bath
PoolA/CWiFiBalcony
$277/night
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5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!

5 Star Back Cove Hide-Away<br>1 bedroom Back Cove apartment with water views!

1 bed 1 bath
PoolA/CWiFiBalcony
$351/night
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Historic Home in the West End. Private Parking.

Historic Home in the West End. Private Parking.

1 bed 2 baths
PoolA/CWiFiBalcony
$263/night
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Spacious Townhome Style Apt

Spacious Townhome Style Apt

3 beds 1 bath
PoolA/CWiFiBalcony
$126/night
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Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking

1 bed 1 bath
PoolA/CWiFiBalcony
$269/night
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Back Cove Gem ★ 5 Min to Old Port ★ Bright and New

Back Cove Gem ★ 5 Min to Old Port ★ Bright and New

2 beds 1 bath
PoolA/CWiFiBalcony
$271/night
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Ocean view Victorian

Ocean view Victorian

1 bath
PoolA/CWiFiBalcony
$325/night
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Fabulous studio apartment with roof deck

Fabulous studio apartment with roof deck

1 bed 1 bath
PoolA/CWiFiBalcony
$250/night
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Beautiful Old Port Apt-Downtown

Beautiful Old Port Apt-Downtown

2 beds 1 bath
PoolA/CWiFiBalcony
$518/night
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Vibrant and stylish pet-friendly 2 BR apt w/king bed, downtown w/parking!

Vibrant and stylish pet-friendly 2 BR apt w/king bed, downtown w/parking!

2 beds 1 bath
PoolA/CWiFiBalcony
$409/night
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Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2

Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2

1 bed 1 bath
PoolA/CWiFiBalcony
$386/night
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Adorable Peaks Island Cottage

Adorable Peaks Island Cottage

1 bed
PoolA/CWiFiBalcony
$244/night
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Downtown Loft with Water Views

Downtown Loft with Water Views

1 bed 1 bath
PoolA/CWiFiBalcony
$372/night
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Historic Munjoy Hill Retreat-Rooftop Water Views!

Historic Munjoy Hill Retreat-Rooftop Water Views!

2 beds 3 baths
PoolA/CWiFiBalcony
$499/night
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“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Parking!

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

2 beds 2 baths
PoolA/CWiFiBalcony
$899/night
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Vintage Maine & Modern Convenience in Portlands Exclusive East End

Vintage Maine & Modern Convenience in Portlands Exclusive East End

2 beds 1 bath
PoolA/CWiFiBalcony
$395/night
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Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!

2 beds 1 bath
PoolA/CWiFiBalcony
$489/night
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Rent a room in the gorgeous Holt House

Rent a room in the gorgeous Holt House

1 bed 1 bath
PoolA/CWiFiBalcony
$175/night
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Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade

Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade

1 bed 1 bath
PoolA/CWiFiBalcony
$283/night
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Entire House Deering Highlands

Entire House Deering Highlands

3 beds 2 baths
PoolA/CWiFiBalcony
$474/night
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Inn at Park Spring 1 - Self Check In - Parking

Inn at Park Spring 1 - Self Check In - Parking

1 bed 1 bath
PoolA/CWiFiBalcony
$331/night
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Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

1 bed 1 bath
PoolA/CWiFiBalcony
$248/night
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Charming, Secluded, Island Getaway!

Charming, Secluded, Island Getaway!

2 beds 1 bath
PoolA/CWiFiBalcony
$260/night
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Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style

Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style

2 beds 2 baths
PoolA/CWiFiBalcony
$339/night
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Charming Downtown West End 2BR

Charming Downtown West End 2BR

2 beds 1 bath
PoolA/CWiFiBalcony
$413/night
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Beautifully Spacious with Charm

Beautifully Spacious with Charm

2 beds 1 bath
PoolA/CWiFiBalcony
$130/night
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Skolfield Inn | Parking | Self-check-in | Garden 1

Skolfield Inn | Parking | Self-check-in | Garden 1

1 bed 1 bath
PoolA/CWiFiBalcony
$269/night
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Rent a room in the gorgeous Holt House

Rent a room in the gorgeous Holt House

1 bed 1 bath
PoolA/CWiFiBalcony
$175/night
View Details → Book on VRBO
Welcome to Your Portland Haven: A Charming & Bright 2BR Retreat

Welcome to Your Portland Haven: A Charming & Bright 2BR Retreat

2 beds 2 baths
PoolA/CWiFiBalcony
$502/night
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Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

2 beds 1 bath
PoolA/CWiFiBalcony
$453/night
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Classic Maine home in quiet tree-lined street neighborhood with fenced in yard

Classic Maine home in quiet tree-lined street neighborhood with fenced in yard

2 beds 2 baths
PoolA/CWiFiBalcony
$208/night
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Quiet Downtown 2BR Oasis - “The Nomad”

Quiet Downtown 2BR Oasis - “The Nomad”

2 beds 1 bath
PoolA/CWiFiBalcony
$166/night
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Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

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

3 beds 2 baths
PoolA/CWiFiBalcony
$439/night
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Local Landmark! Gorgeous Historic Home

Local Landmark! Gorgeous Historic Home

2 beds 1 bath
PoolA/CWiFiBalcony
$519/night
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Best Ocean View In Portland!

Best Ocean View In Portland!

2 beds 1 bath
PoolA/CWiFiBalcony
$612/night
View Details → Book on VRBO

Showing 48 of 294 properties

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