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Holiday Rentals near DiMillo's Old Port Marina

1 Long Wharf, Portland, Maine 04101-4725
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    Travellers to Portland are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 87 Rentals in Portland
    0.2 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Portland, Maine - East End Rental1 / 11
    (30)Very good
    0.9 kilometres from DiMillo's Old Port Marina
    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
    2.7 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    0.2 kilometres from DiMillo's Old Port Marina
    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
    0.2 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Patio
    • Wi-Fi
    • Washer
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    • 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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    Portland, Maine
    Condo/Apartment - 3 Bedrooms, 6 Bathrooms, Sleeps 9
    0.2 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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
    Willard Beach Get Away - Dog Friendly1 / 13
    (2)Excellent
    2.2 kilometres from DiMillo's Old Port Marina
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Balcony
    • DVD Player
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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 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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    South Portland, Maine
    Condo/Apartment - 1 Bathroom, Sleeps 3
    3.7 kilometres from DiMillo's Old Port Marina
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Suitability
    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
    Classic, cozy family cottage with modern amenities and ocean view from porch1 / 20
    (2)Excellent
    4.2 kilometres from DiMillo's Old Port Marina
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 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
    2.6 kilometres from DiMillo's Old Port Marina
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Grill
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    • Balcony
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    • 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 13
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    3.8 kilometres from DiMillo's Old Port Marina
    5 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Wi-Fi
    • Private Garden
    • Secure Parking
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    Pet friendly
    Kid friendly
    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
    Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch1 / 11
    (1)Excellent
    4.2 kilometres from DiMillo's Old Port Marina
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    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
    5.7 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    • Central Heating
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    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
    0.9 kilometres from DiMillo's Old Port Marina
    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 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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    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.8 kilometres from DiMillo's Old Port Marina
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Terrace
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    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    4.5 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Terrace
    • Hot Tub
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    • Internet Access
    • Patio
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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
    5.6 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.4 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Location Information
    Peaks Island, Portland
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    4.6 kilometres from DiMillo's Old Port Marina
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    South Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1.4 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    • Terrace
    • Parking
    • Porch
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    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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    Portland, Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 9
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    3.5 kilometres from DiMillo's Old Port Marina
    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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    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    1.4 kilometres from DiMillo's Old Port Marina
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
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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
    1.3 kilometres from DiMillo's Old Port Marina
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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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    Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Cozy Apartment in Woodfords Corner1 / 14
    (42)Excellent
    2.7 kilometres from DiMillo's Old Port Marina
    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
    1.3 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Beautifully rental with private roof deck1 / 38
    (15)Very good
    0.9 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1200 Sq Ft ♦ West End Gem ♦ Perfect Location1 / 18
    (36)Excellent
    1.1 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    West End Retreat * The Arts District1 / 49
    (19)Excellent
    1.0 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Portland, Maine
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Portland B&B room - steps from Eastern Prom and beach and close to town too!1 / 25
    (10)Very good
    1.4 kilometres from DiMillo's Old Port Marina
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure.1 / 20
    (106)Excellent
    0.2 kilometres from DiMillo's Old Port Marina
    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
    4.3 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Portland, Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Beautiful House Rental At Diamond Cove At Great Diamond Island1 / 24
    (15)Excellent
    5.2 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Portland's Coolest Neighborhood. Easy Walking to Park, Restaurants and More.1 / 17
    (33)Excellent
    1.4 kilometres from DiMillo's Old Port Marina
    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
    1.7 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    PORTLAND PENINSULA-SPACIOUS WALKABLE EAST END SPOT1 / 42
    (8)Excellent
    1.1 kilometres from DiMillo's Old Port Marina
    1 Bedroom, 1 Bathroom, Sleeps 12 Quick View
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    Location Information
    Portland, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 12
    1200 sq ft ♦ West End Townhouse ♦ Perfect Location1 / 16
    (23)Very good
    1.4 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Portland, Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Chic One Bedroom Apartment In Portland's Arts District1 / 24
    (112)Excellent
    1.2 kilometres from DiMillo's Old Port Marina
    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
    1.6 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Walk to Old Port ♦ West End Condo ♦ Parking1 / 14
    (7)Excellent
    1.6 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Portland, Maine
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Sleek condo w/ unbelievable water views - newly renovated, walk to bay!1 / 24
    (11)Excellent
    1.5 kilometres from DiMillo's Old Port Marina
    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
    4.5 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Location Information
    Peaks Island, Portland
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Historic Post Hospital on private Casco Bay Island1 / 23
    (12)Excellent
    4.2 kilometres from DiMillo's Old Port Marina
    10 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    Peaks Island, Portland
    Holiday Rental House - 10 Bedrooms, 3 Bathrooms, Sleeps 18
    Minutes to Everything Portland!1 / 15
    (5)Very good
    1.9 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Fabulous studio apartment with roof deck1 / 27
    (2)Average
    1.2 kilometres from DiMillo's Old Port Marina
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
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    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Stunning White Water Ocean Views From This Peaks Island Home1 / 27
    (6)Excellent
    4.9 kilometres from DiMillo's Old Port Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Beautiful, Modern Loft Close to Ocean and Old Port1 / 26
    (47)Excellent
    1.2 kilometres from DiMillo's Old Port Marina
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Reviewed 19 July 2019
    Walking distance to beautiful Eastern Prom and the Old Port. The apartment was ultra clean with unexpected amenities such as coffee, spices, olive oil, salt & pepper...
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    Location Information
    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    Historic Island Cottage, 5BR1 / 24
    (10)Excellent
    3.6 kilometres from DiMillo's Old Port Marina
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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
    (15)Excellent
    4.1 kilometres from DiMillo's Old Port Marina
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
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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
    (47)Very good
    1.5 kilometres from DiMillo's Old Port Marina
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Spacious Historic 1st Floor Apartment1 / 30
    (17)Excellent
    2.5 kilometres from DiMillo's Old Port Marina
    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
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