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Holiday Homes in Portland

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    Travellers to Portland are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 15 Rentals in Portland
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    Majestic Garden Condo Featuring Private Outdoor Space Downtown/West-End Portland1 / 21
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Portland, Maine - East End Rental1 / 11
    (30)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Portland, ME - East End Garden Suite1 / 6
    (2)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Shared Garden
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2014
    We stayed here for 3 days while in Portland. The apartment was fairly clean and we were about a eight to ten minute drive from downtown. We didn't have very many options because...
    Reviewed 25 October 2013
    Very nice, cute, and tasteful, yet simple, first floor apartment in a great location. Plenty of space and natural light with separate rooms, versus open design, which I found to...
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    About this property
    Visit Portland, Maine!!! We offer a sweet, quirky, first floor, 1-bedroom, one bath (vintage tub with shower) living space for weekly rentals. East end - Congress Street, foot of Munjoy Hill, city side, (near Otto's Pizza Cafe) great area!!! Very sunny, non-smoking building with courtyard access! A...
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    Location Information
    04102, Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Terrace
    • Patio
    • Grill
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful, newly renovated bungalow in the WIllard Beach neighborhood is the latest creation of the well-known and highly respected SoPo Cottage team! Completed in August 2016, It is now being offered for the first time as a vacation rental home. This beautiful home is comfortable for 2...
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    04106, Portland, Maine
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 16
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Porch
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit Portland, Maine: Very comfortable updated apartment in vintage building 2 blocks from the Eastern Prom and the East End Beach, and a 15 minute walk from Portland's Old Port and downtown. This is a vintage fully renovated, second floor, 1 flight walk-up, 3-bedroom living space. There is...
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    04101, Portland, Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • Porch
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Why stay in a hotel when you can enjoy a fully equipped 500 square foot apartment in downtown Portland for half the price? North Street is often regarded as the one of the nicest streets on the 'Hill' and you will not be disappointed in this compact but well equipped urban apartment with driveway...
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    04101, Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Washer
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Located in Portland’s Munjoy Hill neighborhood, this 3BR/3BA property is a homey respite for your East Coast adventure. The prime location is two blocks to the Eastern Promenade, with an amazing view of Casco Bay’s islands. Completely renovated inside and out, this...
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    04101, Portland, Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This historic patio home has a charming cottage feel with all the updated amenities that you want on vacation.  This tastefully furnished 3 bedroom (1 Queen, 1 Queen, 1 bunk bed), 1 1/2 bath home offers hardwood floors throughout, soaring ceilings, open living space ideal for entertaining, a...
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    04109, Portland, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1100 sqft apartment in an 1850 house mixes modern comfort with an Asian flair given by curios and mementos gathered during my many journeys to Asia. Unlike many listings, this really is my home, and I hope to find guests who will enjoy its uniqueness, and respect all that I have gathered over...
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    Location Information
    04102, Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Parking
    • Grill
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of the city's historic West End. Just 1-2 blocks from some of the best restaurants, bakeries, coffee shops, bars and music venues in the city. The perfect home base to explore Portland's foodie scene and all the city has to offer. Our historic home was renovated in 2008 into...
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    Location Information
    04102, Portland, Maine
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • DVD Player
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Why book a hotel when you can stay in a spacious two story condo with plenty of room for everyone? This unit has no personal items giving it a hotel like feel. Great location! Close to Portland International Jetport and Downtown Portland the 'Old Port'. This two-story townhome has two bedrooms...
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    Location Information
    04102, Portland, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Internet Access
    • Patio
    • Washer
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the historic charm of Portland in contemporary style at this two-bedroom condo, where you'll enjoy a sparkling living space, a private balcony, and a tranquil-yet-convenient location for exploring this beautiful city. This modern condo is located in Portland's East End, just two blocks...
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    Location Information
    04101, Portland, Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover a bright, airy escape in the heart of downtown Portland at this three-bedroom condo, a simple, modern retreat with a private deck and an unbeatable location within steps of the Old Port and fantastic restaurants. You'll find this condo in one of the classic red brick buildings that...
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    Location Information
    04101, Portland, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Parking
    • Washer
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Designed by renowned architect John Calvin Stevens, this 4BR, 2.5BA Portland home (dating back to the 1920s) feels truly unique with vintage furnishings and period features throughout. Alongside its historic charms, the home features modern comforts including a nicely updated chef’s kitchen. On...
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    Location Information
    04102, Portland, Maine
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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