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Holiday Rentals in Portland

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    Travellers to Portland are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 17 Rentals in Portland
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    Portland, Maine - East End Rental1 / 22
    (30)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Majestic Garden Condo Featuring Private Outdoor Space Downtown/West-End Portland1 / 38
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Portland, Maine 04101
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1,400 SF of Living Space with a Fenced back yard Fantastic space with high ceilings, modern kitchen and room for 8. Washer & Dryer on site, close to all things Portland without being directly in the bustle of downtown. Great for families with dogs or folks in town for all of the amazing music...
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    Portland, Maine 04103
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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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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    Portland, Maine 04106
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 16
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    5 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Wi-Fi
    • Private Garden
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Entire 2nd and 3rd floors of a Duplex. I promise it will be comfy, clean and adorable. A quick reminder that this is a second floor apartment with hardwood floors. You will have to be considerate of the people on the first floor. The yard is great but I cannot have parties at all. This is not that...
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    Portland, Maine 04103
    Condo/Apartment - 5 Bedrooms, 1 Bathroom, Sleeps 10
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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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    Portland, Maine 04101
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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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
    Portland, Maine 04102
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Comfort | Location | Charm1 / 6
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2018
    Portland is a wonderful city and Kim's apartment is the perfect home base. All we hoped for and more... reflected accurately on the website.
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    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
    Portland, Maine 04102
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Ocean Views
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the heart of Downtown Old Port! This unit provides all the essentials and more. It has luxurious linens, a full kitchen, Smart TV, WiFi, games, books and so much more. You are really staying in style here while living in luxury. The unit screams Portland with all of its character...
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    Portland, Maine 04101
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Old Port! Right in the heart of the Old Port near everything! This unit provides all the essentials and more. It has luxurious linens, a full kitchen, TV, Roku, WiFi, games, books and so much more. You are really staying in style here while living in luxury. The unit screams...
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    Portland, Maine 04101
    Condo/Apartment - 3 Bedrooms, 2 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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    Portland, Maine 04109
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Parking
    • Terrace
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Drenched with natural light, the beautifully restored living area blends modern elements seamlessly with original historic detail. Unwind on the plush sleeper sofa or curl up on the armchair to enjoy a show on the 48” flat screen TV. KITCHEN & DINING Create tasty dishes in the well-equipped...
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    Location Information
    Portland, Maine 04101
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    • Grill
    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
    Portland, Maine 04101
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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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    Portland, Maine 04101
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Portland for your upcoming New England getaway and revel in a luxurious home base when you stay in this sleek one-bedroom condo near Casco Bay. Enjoy unbelievable water views from the patio and easy access to a greenbelt and park offering a number of outdoor activities. Walk to Casco Bay...
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    Location Information
    Portland, Maine 04101
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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