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Holiday Apartments in Westbrook

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    All 34 Rentals in Westbrook
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    Westbrook
    5 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    Westbrook
    7 Bedrooms, 3 Bathrooms, Sleeps 23 Quick View
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    Westbrook
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Westbrook
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
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    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * Please note that there are long-term and short-term tenants on site, in a completely separate unit, with some shared amenities * Escape from your daily routine to this quaint 1-bed, 1-bath vacation rental apartment just 15 minutes from downtown Portland! Whether you soak up the sun on East End...
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    04092, Westbrook, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Westbrook
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * Please note that there are long-term and short-term tenants on site, in a completely separate unit, with some shared amenities * Book your Portland-area escape to this cozy 1-bed, 1-bath vacation rental apartment just outside of the city! This quaint first-floor unit sleeps 4, with room for 2...
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    Location Information
    04092, Westbrook, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    The following rentals are within 10 kilometres of Westbrook.
    Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Old Port! Right in the heart of the Old Port near everything! The unit has luxurious linens, a full kitchen, TV, Roku, WiFi, games, books, coffee, an espresso maker, soap, shampoo, conditioner, hairdryer, iron and so much more. Please note, this unit is absolutely amazing, however, it...
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    Location Information
    04101, Portland, Maine
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Garden Condo Featuring Outdoor Space, Walk Downtown, Old-Port1 / 20
    (6)Very good
    Portland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Private Garden
    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 September 2018
    This little cozy cottage was perfect for me and my wife. It was very clean and comfortable with a full kitchen. We walked to everything and never had to use the car to get...
    Reviewed 5 January 2018
    Great find in the West End with easy access to a ton of restaurants and attractions! This neighborhood is beautiful, definitely one of Portland’s finest! The condo is tucked...
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    About this property
    This magnificent California style, private condo, is located in the heart of the West End of Portland, couple blocks from the heart of Downtown and The Old-Port, walking distance to anywhere around galleries, restaurants, coffee shops, pubs, microbreweries, retails stores, and the museums. Stay at...
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    04101, Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Portland, Maine - East End Rental1 / 11
    (30)Very good
    Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Outdoor Dining Area
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2017
    Apartment was clean, comfortable and nice for our stay. The location was convenient to restaurants, pubs and other attractions in the city. we were able to walk to everywhere...
    Reviewed 24 August 2017
    We had a great girls weekend on the third floor of the East End rental. The house was so clean and spacious and was in walking distance (a mile) of the downtown area. Thank you...
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    About this property
    Visit Portland, Maine!!! We offer a newly renovated, quirky, third floor, 2 flight walk-up, 3-bedroom, living space for weekly rentals. There are two bathrooms - one bath (vintage tub plus separate shower) and second half bath is off front bedroom. East end - Congress Street, foot of Munjoy Hill,...
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    04101, Portland, Maine
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Portland
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • 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
    04101, Portland, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Portland
    3 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Ocean Views
    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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    Location Information
    04101, Portland, Maine
    Condo/Apartment - 3 Bedrooms, 6 Bathrooms, Sleeps 9
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    Portland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Old Port! Stay like a local and see what Portland has to offer while you stay in this high end and classy unit with windows peering down into the heart of Old Port. The unit has luxurious linens, a full kitchen, TV, Roku, WiFi, games, books, Keurig coffee, pot coffee, pour over...
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    Location Information
    04101, Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Willard Beach Get Away - Dog Friendly1 / 13
    (1)Excellent
    South Portland
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2017
    Great location for visiting all the Portland sights. Located in a quiet section of South Portland just one house from the beach. The owner was friendly and helpful at all stages...
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    About this property
    Perfect for a Maine summer vacation. This completely renovated, 400 sq foot studio apartment is one house away from Willard Beach, 4 blocks to Willard Square, 1 mile from downtown South Portland, and a 5 minute drive to downtown Portland, ME. The apartment has a full bath, a kitchenette, air...
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    Location Information
    04106, South Portland, Maine
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    Portland
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Downtown Old Port! Stay like a local in this sleek, stylish and comfortable 2 bedroom condo close to it all. This stylish space has been fully renovated yet still exposes so much of the character of it's past. Walk right outside to be met with all that Portland has to offer in it's...
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    Location Information
    04101, Portland, Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Central Heating
    • Wi-Fi
    • Balcony
    • Terrace
    • Cable/satellite TV
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The East Ender 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,...
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    Location Information
    04101, Portland, Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Portland
    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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    Location Information
    04103, Portland, Maine
    Condo/Apartment - 5 Bedrooms, 1 Bathroom, Sleeps 10
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    Portland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sandy Toes and Beautiful Views Stroll the gorgeous shores of Casco Bay when you escape to this two-bedroom condo, a beautifully renovated Portland retreat with a dog-friendly interior, a private patio, and a wonderful location within steps of restaurants and recreation! This condo is located in...
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    Location Information
    04101, Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Portland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront View Escape Come to Portland for your upcoming New England getaway and revel in a luxurious home base when you stay in this sleek two-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...
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    Location Information
    04101, Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Waterfront Fun Pet Friendly Vacation Rental Camp1 / 23
    (9)Very good
    Gorham
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Terrace
    • Porch
    • Patio
    • Parking
    • Balcony
    • Grill
    • Central Heating
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2017
    Peaceful and quiet cottage on wooded lot along the river. The boats with life jackets just made it extra special for our family to explore! Inside the comfy beds had nice...
    Reviewed 23 August 2016
    Great rental. Very relaxing and quiet. Really clean and fully stocked with everything you would need. Just bring yourself and food. We loved it here and was sad when vacation...
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    About this property
    Waterfront camp in Maine for weekly rent that offers peace, relaxation and fun for a family or small group. The camp is located on the Presumpscot River in Gorham, Maine. So unique and offers up 5 to sleep comfortably in any of the 2 bedrooms and an L-shaped couch in the living room. A...
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    Location Information
    04038, Gorham, Maine
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Portland
    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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    Location Information
    04103, Portland, Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!1 / 72
    (3)Excellent
    South Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2017
    My husband and I visited in late October from the Houston area. We were looking for a change of pace and East Coast charm and were not disappointed. The house was located in a...
    Reviewed 18 June 2017
    My husband, sister, two teenagers, and I stayed for 10 days in May. We loved it so much, we didn't want to leave. The cottage is beautifully decorated, with views of Casco...
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    About this property
    BRAND NEW TO MARKET! Accepting winter thru fall reservations now. Beautifully renovated 3 Bedroom, 1.5+ bath turn-of-the-century seaside home features beautiful views of the Portland shipping channel and the islands of Casco Bay and is just 100 yards to Willard Beach. Sleeps 7-9. This...
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    Location Information
    04106, South Portland, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Portland, ME - East End Garden Suite1 / 6
    (2)Average
    Portland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • Shared Garden
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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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    South Portland
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Balcony
    • Washer
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully renovated house was stripped down to the studs for a full-scale renovation. Beautifully designed and completely renovated by a highly recognized designer, the house retains the original 1906 Dutch Colonial charm, but was creatively reimagined for today's open-concept and luxurious...
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    Location Information
    04106, South Portland, Maine
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    Portland
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • 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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    Location Information
    04101, Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore Maine’s breathtaking and dramatic coastline dotted with appealing villages, islands, and lighthouses from the cozy comfort of this sunny 2BR/1.5BA duplex. The convenient location is within walking distance of the beach, eateries, and shopping. Relax in your quaint-meets-modern New England...
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    04106, South Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Portland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Life is better with an ocean view! There are wonderful OCEAN VIEWS! VERY close to the beach! Right here in the quiet beachfront community of Willard Beach in South Portland, there are lots of things to do and see VERY CLOSE BY, and many are within walking distance! The inside is gorgeous and...
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    Location Information
    04106, South Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “Top of Munjoy Hill” is part of Portland Maine’s evolving Munjoy Hill Historic District. Lafayette Street is quiet, just two blocks long, but close to everything. There are bustling shops, restaurants, bakeries, markets and a busy performing arts center within a short stroll along brick...
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    Location Information
    04101, Portland, Maine
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Portland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This new 1BR South Portland cottage is perfect for a couple but offers plenty of space for entertaining. You’re just 10 minutes from all of the historical buildings and restaurants of downtown Portland. Take a boat cruise or stroll through town. Sleeps 2. ABOUT THE COTTAGE Enter this brand-new,...
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    Location Information
    04106, South Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Portland
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • 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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    Location Information
    04106, Portland, Maine
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Life is better with OCEAN VIEWS and a 3-minute walk to the beach! This NEWLY refurbished, bright, well decorated, and spacious unit will delight you! OCEAN VIEWS from inside and the big deck with new grill area. See sailboats, lobster boats, birds, islands and more. Located in the quiet beachfront...
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    Location Information
    04106, South Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you'd prefer being walking distance to Portland's best beaches and parks, but want a modern, sleek and private apartment, look no further. Accommodating up to 2x couples or a small family, our recently renovated apartment is ready for your stay. Our place is just 20 min by foot to Portland, or...
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    Location Information
    04106, South Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Comfort | Location | Charm1 / 6
    (1)Excellent
    Portland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
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    Reviewed 2 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
    04102, Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Originally built in 1920, this bright and airy two-level 2BR/1.5BA beachside property features upscale design elements including wood beam ceilings, a gourmet kitchen, and hardwood floors as well as a private fenced yard. Please note this dog-friendly duplex has an adjoining, yet separate, unit...
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    Location Information
    04106, South Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Portland
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    • Terrace
    • Parking
    • Porch
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable vintage Hideaway 3BR in Munjoy Hill w/ Restored Interior & Balcony. 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...
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    Location Information
    04101, Portland, Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 9
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    Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “Top of Munjoy Hill” is part of Portland Maine’s evolving Munjoy Hill Historic District. Lafayette Street is quiet, just two blocks long, but close to everything. There are bustling shops, restaurants, bakeries, markets and a busy performing arts center within a short stroll along brick...
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    Location Information
    04101, Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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