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Vacation Rentals near Old Port

Commercial St, Portland, Maine 04101
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    All 96 Rentals in Portland
    0.2 miles from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Portland, Maine - East End Rental1 / 11
    (30)Very good
    0.3 miles from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    0.2 miles from Old Port
    3 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!1 / 89
    (3)Excellent
    1.7 miles from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed December 31, 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 June 18, 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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    South Portland, Maine
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    0.1 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Skiing: Property Is In A Ski Resort
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Portland! Stay in style in this luxury penthouse style apartment with exposed brick, granite, and high-quality linens. Located right in the heart of the Old Port you will be only a walk away from just about anything you wish to see, not to mention the world-class restaurants and...
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.1 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    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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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Willard Beach Get Away - Dog Friendly1 / 13
    (2)Excellent
    1.4 miles from Old Port
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Grill
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    • Balcony
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2019
    Nice and clean, near the beach in a quiet location everyone was friendly. Beach is dog friendly and 99% of dog owners knew how to manage their dogs off leash. No more water than...
    Reviewed August 17, 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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    South Portland, Maine
    Condo/Apartment - 1 Bathroom, Sleeps 3
    2.4 miles from Old Port
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Beautiful and spacious renovated colonial with 4 bedrooms plus a den with sleeper sofa. Sleeps 10+. 10 mins to downtown Portland. Private beach rights to gorgeous Casino Beach. Walk to all the shops in the Willard Square area. Walk to Portland headlight in 10 minutes. More information This...
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    Cape Elizabeth, Maine
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Classic, cozy family cottage with modern amenities and ocean view from porch1 / 20
    (2)Excellent
    2.5 miles from Old Port
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed September 19, 2018
    Woody and Comfort’s house is fantastic. One of the best porches around. Eat your lobster dinner outside on the porch looking at the ocean. This home had a super kitchen as well...
    Reviewed September 19, 2018
    The cottage was utterly perfect, and all that a Maine cottage should be...from the outdoor shower, to the fireplace, to the surprisingly comfortable wicker furniture, to the...
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    About this property
    We close up the cottage during the winter months. Please inquire about rentals May 1 - Columbus Day. The house is simply but completely furnished and colorfully decorated, for family use, not as a 'rental property.' Virtually everything in the cottage has some sentimental value, having been either...
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    Peaks Island, Portland
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    2.3 miles from Old Port
    5 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    About this property
    Entire 2nd and 3rd floors of a Duplex. 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 kind of neighborhood. Close to all things...
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    Portland, Maine
    Condo/Apartment - 5 Bedrooms, 1 Bathroom, Sleeps 10
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    1.7 miles from Old Port
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Ocean Views
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    Pet friendly
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    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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    South Portland, Maine
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 13
    Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch1 / 11
    (1)Excellent
    2.5 miles from Old Port
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    Reviewed September 20, 2018
    This property was an absolute fantastic place to enjoy a relaxing week on Peaks Island. We rode bikes all around the island, and I don’t think I spotted a better view. The...
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    About this property
    THE COTTAGE IS CLOSED FOR THE WINTER MONTHS. PLEASE INQUIRE ABOUT THE 2018 SEASON THAT BEGINS IN MAY! Our spacious but cozy family cottage is located on a quiet shorefront road, just a few yards from the water with an uninterrupted view of Josiah's Cove and then across the sparkling sea 'all the...
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    Peaks Island, Portland
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Cozy Single Family Cape1 / 11
    (4)Very good
    3.4 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Smoking allowed
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    Peaks Island, Portland
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    1.2 miles from Old Port
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Terrace
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    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Portland, ME - East End Garden Suite1 / 6
    (2)Average
    0.4 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Shared Yard
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 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 October 25, 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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    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2.9 miles from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
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    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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    Cape Elizabeth, Maine
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    2.7 miles from Old Port
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Terrace
    • Hot Tub
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    Pet friendly
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    Portland, Maine
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
    3.3 miles from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Portland, Maine
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.2 miles from Old Port
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Peaks Island, Portland
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    2.7 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    * TurnKey photo-verifies this home is professionally cleaned with products approved by the EPA for use against COVID-19. Bookings at this home include a 24-hr buffer between guest stays through June 2020. * This new 1BR South Portland cottage is perfect for a couple but offers plenty of space for...
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    South Portland, Maine
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1.8 miles from Old Port
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Note that per Executive Order No. 34 FY 19/20, until at least 5/31/20, lodging may be provided only for the following purposes: Housing vulnerable populations, including children in emergency placements, persons at risk of domestic violence, and homeless individuals as permitted by the State;...
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    South Portland, Maine
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    3.8 miles from Old Port
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Note that per Executive Order No. 34 FY 19/20, until at least 5/31/20, lodging may be provided only for the following purposes: Housing vulnerable populations, including children in emergency placements, persons at risk of domestic violence, and homeless individuals as permitted by the State;...
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    Cape Elizabeth, Maine
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3.7 miles from Old Port
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Note that per Executive Order No. 34 FY 19/20, until at least 5/31/20, lodging may be provided only for the following purposes: Housing vulnerable populations, including children in emergency placements, persons at risk of domestic violence, and homeless individuals as permitted by the State;...
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    Cape Elizabeth, Maine
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.7 miles from Old Port
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    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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    Portland, Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 9
    1.9 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Our location puts you as close to magnificent natural beauty as it does to city amenities. 3-5 min (car) or 15-25 min (walk/bike beautiful trails along Casco Bay) to the old port/down town . Alternatively; go left over Presumpscot Bridge towards Falmouth Foreside and explore Mackworth Island,...
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    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    0.9 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Enjoy your relaxing weekend in Portland with this wonderfully located 1 bedroom apartment located downtown! During your stay you can walk five minutes to Portland favorites such as Tandem Coffee Shop, Hot Suppa, and Bramhall. Other fun activities include watching a SeaDog’s game or visiting the...
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    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Comfort | Location | Charm1 / 6
    (1)Excellent
    0.9 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed August 1, 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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    Portland, Maine
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Cozy Apartment in Woodfords Corner1 / 14
    (42)Excellent
    1.6 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Portland, Maine
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Family friendly and close to beach! Sleeps nine.1 / 27
    (3)Excellent
    3.1 miles from Old Port
    4 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    Portland, Maine
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 9
    1200 Sq Ft ♦ West End Gem ♦ Perfect Location1 / 18
    (36)Excellent
    0.8 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure.1 / 20
    (105)Excellent
    0.0 miles from Old Port
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Dog Friendly 2.5 Bedroom With Fenced In Yard1 / 15
    (34)Excellent
    2.7 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Portland, Maine
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Beautiful House Rental At Diamond Cove At Great Diamond Island1 / 24
    (15)Excellent
    3.1 miles from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Portland, Maine
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    PORTLAND PENINSULA-SPACIOUS WALKABLE EAST END SPOT1 / 42
    (8)Excellent
    0.5 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 12 Quick View
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    Portland, Maine
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 12
    Chic One Bedroom Apartment In Portland's Arts District1 / 24
    (112)Excellent
    0.8 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Glorious getaway on Portland's Eastern Promenade.1 / 25
    (36)Excellent
    0.8 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Sleek condo w/ unbelievable water views - newly renovated, walk to bay!1 / 24
    (11)Excellent
    0.7 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Cozy Island Village Cottage With Easy Ferry Ride to Portland1 / 13
    (10)Very good
    2.7 miles from Old Port
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Peaks Island, Portland
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Historic Post Hospital on private Casco Bay Island1 / 23
    (12)Excellent
    2.6 miles from Old Port
    10 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    Peaks Island, Portland
    Rental Home - 10 Bedrooms, 3 Bathrooms, Sleeps 18
    Minutes to Everything Portland!1 / 15
    (5)Very good
    1.3 miles from Old Port
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Stunning White Water Ocean Views From This Peaks Island Home1 / 27
    (6)Excellent
    3.0 miles from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Portland, Maine
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Historic Island Cottage, 5BR1 / 24
    (10)Excellent
    2.1 miles from Old Port
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Peaks Island, Portland
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!1 / 4
    (15)Excellent
    2.5 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Peaks Island, Portland
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Spacious Historic 1st Floor Apartment1 / 30
    (17)Excellent
    1.5 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
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    Location Information
    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Sunny Historical West End 2BR1 / 16
    (69)Very good
    1.0 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Spacious 3 bedroom in most desirable neighborhood1 / 11
    (18)Very good
    0.5 miles from Old Port
    3 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Portland, Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 10
    Charming intown two bedroom.1 / 22
    (85)Excellent
    0.2 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Completely renovated, walk everywhere!1 / 12
    (4)Very good
    0.4 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Beautiful Munjoy Hill Private Oasis1 / 20
    (24)Excellent
    0.9 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    “Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!1 / 24
    (48)Excellent
    0.2 miles from Old Port
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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