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South Portland Holiday Homes

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    Travellers to South Portland are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 43 Rentals in South Portland
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    South Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!1 / 67
    (2)Excellent
    South Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    2BR / 1B - Willard Beach -- South Portland1 / 27
    (2)Very good
    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    South Portland
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    South Portland, Maine 04106
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    South Portland
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this quaint cape cod style house. A fun eclectic space to land after a day of shopping in Portland's Old Port, the Maine Mall, the infamous Freeport LL Bean, or dinner out in one of downtown Portland's stellar restaurants. 3 Bedrooms, 1 Bathroom, House features open concept kitchen/living...
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    South Portland, Maine 04106
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    The Willard Beach House (Dog friendly!)1 / 13
    (1)Excellent
    South Portland
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Housekeeping Included
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    Reviewed 15 June 2017
    This was a find. Charming perfect beach house, literally steps from the beach. And dog friendly. Darrell and Judy were perfect hosts, very helpful. We will definitely be back.
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    About this property
    This unique ocean side carriage house is just one house from the ocean. It has one bedroom with a king size bed. A full bath and kitchen. All linens, plates, utensils and glassware included. Air conditioned. Our beach is a quiet, sandy, mile long neighborhood beach on Casco Bay, with views to the...
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    South Portland, Maine 04106
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    New and gorgeous home with private beach access nearby and a shared pool!1 / 24
    (1)Very good
    South Portland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This is a neatly arranged house with all new everything. 10 minutes to Old Port..10 minutes to a private beach in Cape Elizabeth. The owner still has some work to do in making...
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    About this property
    This brand-new, 1,000-square-foot home built for two offers modern appliances and designer decor as well as cutting edge in-home entertainment and access to a private beach a short drive away. Located on Cape Elizabeth, just 10 minutes from downtown Portland, you're close to shopping, dining, and...
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    South Portland, Maine 04106
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Large Home Walk to Beach! Close to all amenities!1 / 26
    (9)Excellent
    South Portland
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Wi-Fi
    • Housekeeping Included
    • DVD Player
    • Private Garden
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2017
    Great house with updated kitchen and large open living/kitchen area and spacious dining room. Perfect for a large group looking for a comfortable, laid-back getaway. We rented...
    Reviewed 31 January 2017
    This home is so wonderful. It has everything you need! The beds were comfortable and the entire place was so clean! It's very close to downtown Portland, only about a $10 uber...
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    About this property
    This property is ideal for providing an excellent accommodation for a family or groups that want to live in comfort for their stay. There are 3 bedrooms and 2.5 baths, with an additional finished basement area that can be used as another bedroom and play area. The house is meticulously cared for...
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    South Portland, Maine 04106
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Washer
    • Grill
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For an amazing stay in a lively area of Portland, this inviting dog-friendly condo has plenty to offer. You'll have a wood stove, a great deck with a gas grill, and a top-notch location within walking distance to lots of fantastic eateries. Located in the heart of Willard Square just a short drive...
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    South Portland, Maine 04016
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Internet Access
    • Grill
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a revitalizing retreat to the charming city of Portland when you stay at this lovely vintage condo. You'll have updated amenities inside, plus a deck and gas grill, and you'll be in close proximity to lots of restaurants nearby in Willard Square. Conveniently located in Willard Square, this...
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    South Portland, Maine 04106
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
    You'll be only one block from Willard Beach at this two-bedroom South Portland condo, a charming and comfortable getaway with a dog-friendly interior, a private outdoor deck, and a wonderful location near lighthouses, shops, restaurants, and the gorgeous shores of Casco Bay. The building, which...
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    South Portland, Maine 04016
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Portland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Satellite TV
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    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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    South Portland, Maine 04106
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The following rentals are within 10 kilometres of South Portland.
    Higgins Beach Maine1 / 8
    (2)Excellent
    Scarborough
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2014
    My friends and I stayed here for a weekend recently and loved every minute of it. The cottage is right down the street from a lovely beach. We enjoyed swimming and watching all...
    Reviewed 24 August 2014
    The write up and pictures of the cottage were accurate. The landlord was wonderful to work with. He was accessible if needed and the cottage was very clean and offered the...
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    About this property
    A classic New England beach house located 75 yards from the sands of Higgins Beach in Scarborough Maine. The cottage has two enclosed sun porches (front and back), a kitchen, dining room, large living space, and half bath on the first floor. The second floor has four bedrooms with twin beds and...
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    Scarborough, Maine 04103
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 bedroom home near beaches1 / 5
    (1)Average
    Cape Elizabeth
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Hot Tub
    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 September 2016
    Great location near Old Port, Portland and Crescent Beach plus Fort Williams. House has great potential but needs more attention to details....as in window coverings for...
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    About this property
    Home ideally located near many beaches(higgins, Crescent, Ferry, Scarborough and ft williams, two lights state park). Steps from the greenbelt trail, near a large fresh water pond with a boardwalk around it that is full of fish and fun to kayak on. Town has many restaurants: sea glass, rudys,...
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    Cape Elizabeth, Maine 04107
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Dog-friendly home with a game room and patio, close to parks, trails & downtown!1 / 24
    (1)Excellent
    Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Parking
    • Washer
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2017
    We had a fantastic time at this property. It was close to downtown, barely a 10 minute drive by car to a wide variety of restaurants, shopping, grocery stores, and parks. The...
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    About this property
    Discover classic New England charm within walking distance of downtown Portland at this three-bedroom home, where you'll enjoy a private patio, a lovely remodeled kitchen, and a wonderful location close to dining and shopping. Built in 1910, this dog-friendly home is located in a quiet neighborhood...
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    Portland, Maine 04103
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Adorable 2 Bdr Cottage Apartment _ Casino Beach1 / 12
    (1)Very good
    Cape Elizabeth
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Shared Garden
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2014
    The owner was very friendly and accommodating. The property is just blocks away from the Portland Head Light and close to beautiful, clean beaches. A very charming and...
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    About this property
    At The Shore - Cape Elizabeth, a small coastal community on Casco Bay at the entrance to Portland Harbor, is a suburb of Maine's largest city, Portland. Cape Elizabeth (pop 8500) is a historic town, famous for its lighthouses, parks, and scenic vistas of Maine's legendary rocky coast. The town sits...
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    Cape Elizabeth, Maine 04107
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 BR 1.5 BA COTTAGE WITH WATER VIEWS OF CASCO BAY1 / 13
    (1)Average
    Peaks Island
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Washer
    • Satellite TV
    • Porch
    • Grill
    • Internet Access
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2016
    This cottage is in a wonderful walk to beach location and close to ferry in sweet little Peaks Island. The owners seem to be very nice and generous with information. The...
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    About this property
    A BEAUTIFUL WATER VIEW OF CASCO BAY OFF THE COAST OF PORTLAND IN THIS 3 BR / 1.5 BA COTTAGE NEWER KITCHEN WITH GRANITE COUNTER TOPS, FULL SIZED DISHWASHER AND 6 BURNER COMMERCIAL GAS OVEN. THE KITCHEN ALSO HAS A LARGE AMOUNT OF POTS, PANS, KITCHEN GADGETS AND LOTS OF PLATES AND SILVERWARE. Island...
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    Peaks Island, Maine 04108
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Portland
    4 Bedrooms, 2 Bathrooms, Sleeps 17 Quick View
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    • Terrace
    • Grill
    • Patio
    • Balcony
    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 17
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    Pine Point Beach Studio condo1 / 22
    (3)Excellent
    Scarborough
    1 Bedroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Washer
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    • Grill
    • Outdoor Dining Area
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2015
    We couldn't believe how close we were to the water. It is such a wonderful location with a great little convenience store practically next door and across from the beach that...
    Reviewed 5 June 2015
    Cozy and very relaxing! The beach is directly across the street. Can hear the ocean waves from the bedroom. Very clean. Perfect central spot between OOB and Portland. My...
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    About this property
    This great studio condo is available starting on the 27th of May for weekly rentals (Saturday to Saturday) throughout the summer. This unit has a new queen Murphy bed, full kitchen including an apt. size fridge with freezer, stove top, microwave, convection oven, pots, pans, dishware, and utensils....
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    Scarborough, Maine 04074
    Condo/Apartment - 1 Bedroom, Sleeps 2
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    Portland
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Balcony
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    • 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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    Portland, Maine 04101
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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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
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    • 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 26 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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    Cape Elizabeth
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    • Internet Access
    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make yourself at home amid the wonders of Cape Elizabeth at this four-bedroom condo, a dog-friendly Maine escape with a sun-splashed private deck, a spacious interior, and an outstanding location close to beaches, lighthouses, and the excitement of downtown Portland. Ideally situated between South...
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    Cape Elizabeth, Maine 04107
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Portland, Maine - East End Rental1 / 33
    (26)Very good
    Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Terrace
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Outdoor Dining Area
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Perfect apt, loved the layout . Kitchen was amazing, beds were comfy enough. The location for us was spectacular to the Main Street area and the location of the wedding, all...
    Reviewed 31 August 2016
    The location is fabulous! Cozy kitchen, beds okay, bathroom could use a cleaning of all the previously used bars of soap, expired medications. The main problem was a burnt out...
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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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    Portland, Maine 04101
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Scarborough
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    • Private Garden
    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located across the street from the Harbor. The 7 mile white sand beach of Pine Point is a 5 minute walk. You can watch the boats coming an going from the living room picture window. The harbor is a major stopover site for migrating shorebirds. If you like paddling, fishing, birding,...
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    Location Information
    Scarborough, Maine 04074
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Cape Elizabeth
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Custom built eco-friendly home set on 2 acres in seaside Cape Elizabeth. Relax & recharge in a home designed for optimal wellness. Central to all area beaches & only 7 minutes to Portland's fine dining, shopping, & culture. Come enjoy this home's ideal location! This home was designed out of a...
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    Location Information
    Cape Elizabeth, Maine 04107
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Cape Elizabeth
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This ranch style home is located at 4 Two Lights Terrace, in Cape Elizabeth, Maine. It sleeps 6 people and offers 2 bedrooms and 2 baths. The master bedroom offers an in suite bathroom, as well as a king bed with Ralph Lauren bedding for optimal comfort. The guest bedroom is located just off the...
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    Location Information
    Cape Elizabeth, Maine 04107
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Portland
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Private Garden
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    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
    Portland, Maine 04103
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Welcome to the Skybox!! Now renting for July!1 / 19
    (2)Average
    Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Terrace
    • Waterfront
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2013
    Good The location was great, in the east end with tons of restaurants and an easy walk to the old port area. Nice modern building, clean design and nice views. Lots of...
    Reviewed 13 July 2013
    We stayed here for three nights with another couple. The location is great and the view is beautiful. It is on the 4th floor of the building so keep that in mind when packing...
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    About this property
    Ultra Modern Penthouse in Portland's Old Port. Posted 8/23/2015: We have found our renter for this year. We are now accepting reservations for bookings starting July 2016. Uber Modern Flats. Just completing construction and ready for you to rent. This is the 3rd floor of a 4 story building....
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    Location Information
    Portland, Maine 04101
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Scarborough
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Housekeeping Included
    • Hot Tub
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have a large 4 bedroom house that is perfectly located in Ogunquit. Fully stocked kitchen, dining room, living room with 50' TV, 2 full baths, two porches, parking and limited housekeeping service. Also included is use of our pool and hot tub and complimentary continental breakfast for all...
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    Location Information
    Scarborough, Maine 04106
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cape Elizabeth
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Ocean Views
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom home overlooks Crescent Beach and Richmond Islands. Sun rises over strawberry fields and affords sunsets over the ocean. Short walk to beach. Sunroom open to dining and living room. Downstairs bedroom with twin beds, separate bath and living area. Large master bedroom with...
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    Location Information
    Cape Elizabeth, Maine 04107
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Peaks Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nicely furnished townhome has 3 bedrooms (Queen, Queen, Bunk beds) and 1 1/2 baths. Inviting and comfortable furnishings, nice open floor plan, finished room in basement, and a great covered porch with pretty views of the landscaped grounds. This unit also offers bikes and kayaks for your use. All...
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    Peaks Island, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Peaks Island
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    This 4 bedroom, 2 1/2 bath home is a beautifully crafted Victorian home with a cottage feel. Comfy couches and chairs in the living area, a generous size dining area, and a cute efficient kitchen with nice soapstone farm sink. Small porch off the kitchen with grill and spacious front porch with...
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    Peaks Island, Maine
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Peaks Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    About this property
    This is a gem. This cozy historic property is filled with charm and character. Originally the Gatehouse, this quaint duplex offers one floor living and is convenient to both sides of the island, and just a short stroll to tennis, pool, general store, and other island amenities. This one bedroom is...
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    Peaks Island, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Scarborough
    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
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    • Hot Tub
    • Waterfront
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5,400 sq. ft. of living space with 4 stories, 2 balconies, 2 decks and patio, overlooking Pine Point harbor, protected marsh & wild life sanctuary at the estuary of the Scarborough River and Atlantic Ocean. There is a small beach in front of the house and miles of sandy beach (Pine Point Beach &...
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    Location Information
    Scarborough, Maine 04074
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    Peaks Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Sergeant’s Quarters offers 3 Bedrooms and 2 Baths. Guest suite on 3rd level with large skylight for star gazing. Front and back porches with lovely gardens in backyard. The backyard also has a nice patio with table, chairs, and grill… ideal for a summer cookout. Ask about renting the entire...
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    Location Information
    Peaks Island, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Portland
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Terrace
    • Porch
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    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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    Peaks Island
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    About this property
    Victorian historic home that sleeps 12. Impressive craftsmanship throughout, including large living/dining area ideal for a large group. 6 bedrooms, 2 1/2 baths offers lots of room for all. A finished 3rd level has 2 bedrooms, 1 full bath, pool table and comfy area to watch movies. Located at...
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    Peaks Island, Maine
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Peaks Island
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Charming 3+ BR (1 queen, 1 single w/trundle, 1 bunk bed + single, 1 queen) 1 1/2 BA townhome. Enjoy this beautifully furnished home with all the charm and character of an island cottage. Original hardwood floors, open floor concept, soaring ceilings, and light filled rooms. A great basement with...
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    Peaks Island, Maine
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Peaks Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    The perfect island getaway. This cozy historic property is filled with charm and character. Originally the Gatehouse, this quiet duplex offers one floor living and is convenient to both sides of the island, and just a short stroll to tennis, pool, store, and other island amenities. This one...
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    Location Information
    Peaks Island, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Higgins Beach, Baer's Cottage 1 block to beach1 / 13
    (4)Excellent
    Scarborough
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    • Waterfront
    • Grill
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2015
    We had a great time at Baers. BEV treated us like family. We will always stay at Bears. Everything is walking distance. We look forward to staying with her again. Higgins Beach...
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    About this property
    Located in what was once Higgins Beach's Baer's Place convenience store, this rental has a mix of old and new. Not your typical beach decor, but made for beach living. The open floor plan means you can all be together and still have your space. It has three bedrooms, one with a king size memory...
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    Location Information
    Scarborough, Maine 04074
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Portland
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    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
    Portland, Maine 04102
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Portland
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    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
    Portland, Maine 04102
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Portland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This magnificent California style 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 with us in...
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    Location Information
    Portland, Maine 04101
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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