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Holiday Rentals near Old Port

Commercial St, Portland, Maine 04101
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    Travellers to Portland are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 71 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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    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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    0.2 miles from Old Port
    3 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Patio
    • Wi-Fi
    • Washer
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the heart of Downtown Old Port! This unit provides all the essentials and more. It has luxurious linens, a full kitchen, Smart TV, WiFi, games, books and so much more. You are really staying in style here while living in luxury. The unit screams Portland with all of its character...
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    Portland, Maine
    Condo/Apartment - 3 Bedrooms, 6 Bathrooms, Sleeps 9
    0.1 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • 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
    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
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 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 17 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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    South Portland, Maine
    Condo/Apartment - 1 Bathroom, Sleeps 3
    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
    • Wi-Fi
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    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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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2.4 miles from Old Port
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    2.3 miles from Old Port
    5 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
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    Smoking allowed
    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
    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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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 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 19 September 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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    Location Information
    Peaks Island, Portland
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    1.7 miles from Old Port
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Grill
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    • 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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    South Portland, Maine
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    0.7 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Wi-Fi
    • Balcony
    • Terrace
    • Cable/satellite TV
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    • 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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    Portland, Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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 20 September 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
    Holiday Rental House - 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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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Location Information
    Peaks Island, Portland
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    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 Garden
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    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2014
    We stayed here for 3 days while in Portland. The apartment was fairly clean and we were about a eight to ten minute drive from downtown. We didn't have very many options because...
    Reviewed 25 October 2013
    Very nice, cute, and tasteful, yet simple, first floor apartment in a great location. Plenty of space and natural light with separate rooms, versus open design, which I found to...
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    About this property
    Visit Portland, Maine!!! We offer a sweet, quirky, first floor, 1-bedroom, one bath (vintage tub with shower) living space for weekly rentals. East end - Congress Street, foot of Munjoy Hill, city side, (near Otto's Pizza Cafe) great area!!! Very sunny, non-smoking building with courtyard access! A...
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    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    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
    Kid friendly
    Smoking allowed
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
    0.7 miles from Old Port
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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    About this property
    Turner Street Collection Find the perfect blend of the modern and the classic at this three-condo property in Portland, where the beauty of Maine is on full display. Offering three sleek kitchens, top-floor views of the water, and a location within walking distance of the Eastern Promenade and...
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    Portland, Maine
    Condo/Apartment - 6 Bedrooms, 3 Bathrooms, Sleeps 14
    1.9 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Ocean Views
    • Balcony
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    • Waterfront
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    0.7 miles from Old Port
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    • Terrace
    • Parking
    • Porch
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    • Balcony
    • Washer
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    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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    Portland, Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 9
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    0.7 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Sandy Toes and Beautiful Views Stroll the gorgeous shores of Casco Bay when you escape to this beautifully renovated Portland retreat with a private patio and a wonderful location just steps from restaurants and recreation! This condo features hardwood and tile floors and a sleek color palette of...
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    Portland, Maine
    Condo/Apartment - 2 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. * 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...
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    Location Information
    South Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.4 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    A Foodie’s Delight Polished, elegant, and perfectly located within walking distance of the Old Port, this beautiful condo offers a wonderful, comfortable retreat right in the very heart of Portland. You'll have a beautifully-styled kitchen with stainless steel appliances, at-home comforts that...
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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 1 August 2018
    Portland is a wonderful city and Kim's apartment is the perfect home base. All we hoped for and more... reflected accurately on the website.
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    About this property
    This 1100 sqft apartment in an 1850 house mixes modern comfort with an Asian flair given by curios and mementos gathered during my many journeys to Asia. Unlike many listings, this really is my home, and I hope to find guests who will enjoy its uniqueness, and respect all that I have gathered over...
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    Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.7 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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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    Portland, Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Charming 2-bedroom steps from the Eastern Promenade1 / 19
    (22)Excellent
    0.6 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Portland B&B room - steps from Eastern Prom and beach and close to town too!1 / 25
    (10)Very good
    0.7 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Portland's Coolest Neighborhood. Easy Walking to Park, Restaurants and More.1 / 17
    (34)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
    Historic West End Neighborhood1 / 15
    (27)Excellent
    1.2 miles from Old Port
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    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
    (37)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
    (14)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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Stunning White Water Ocean Views From This Peaks Island Home1 / 27
    (14)Excellent
    3.0 miles from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Historic Island Cottage, 5BR1 / 24
    (11)Excellent
    2.1 miles from Old Port
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Peaks Island, Portland
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!1 / 4
    (17)Excellent
    2.5 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Location Information
    Peaks Island, Portland
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Polished, modern condo w/ balcony - walk to Eastern Promenade & Casco Bay!1 / 28
    (52)Very good
    0.7 miles from Old Port
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Location Information
    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Adorable Portland getaway on the Eastern Promenade1 / 23
    (15)Excellent
    0.8 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Beautiful Munjoy Hill Private Oasis1 / 20
    (28)Excellent
    0.9 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
    Updated stylish 1 BR in West End1 / 18
    (7)Excellent
    0.7 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Art Filled East End Home a short walk to waterfront, restaurants and shops1 / 29
    (7)Excellent
    0.5 miles from Old Port
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Elegant, Sunny, 2 Bedroom Townhouse Apartment1 / 24
    (88)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/ private patio - less than two blocks from the beach/park1 / 24
    (19)Excellent
    0.7 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
    3BR home: East End neighborhood: walk to ocean or downtown, local eateries1 / 44
    (29)Excellent
    0.7 miles from Old Port
    3 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 10
    Sunset Cottage, Family-Friendly Oasis1 / 20
    (8)Very good
    2.6 miles from Old Port
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Location Information
    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    NEW LISTING ☼ Unique Oceanfront Home1 / 48
    (12)Excellent
    3.4 miles from Old Port
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Peaks Island, Portland
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood1 / 35
    (13)Very good
    1.1 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
    Cozy Getaway In The City1 / 21
    (24)Excellent
    2.2 miles from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Comfortable, Bright, Fun Munjoy Hill -- Steps to Eastern Prom Park1 / 19
    (34)Excellent
    0.7 miles from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1
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