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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 39 Rentals in Portland
    Classic, cozy family cottage with modern amenities and ocean view from porch1 / 20
    (2)Excellent
    4.1 kilometres from Old Port
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch1 / 11
    (1)Excellent
    4.1 kilometres from Old Port
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season1 / 50
    (5)Excellent
    4.4 kilometres from Old Port
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    3.2 kilometres 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
    Charming 2-bedroom steps from the Eastern Promenade1 / 25
    (29)Excellent
    1.0 kilometres 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
    Back Cove Charmer Close to Everything1 / 15
    (31)Very good
    3.0 kilometres 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
    Historic West End Neighborhood1 / 15
    (50)Excellent
    2.0 kilometres 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
    Art Filled East End Home a short walk to waterfront, restaurants and shops1 / 29
    (12)Excellent
    0.9 kilometres from Old Port
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Glorious getaway on Portland's Eastern Promenade.1 / 25
    (51)Excellent
    1.3 kilometres 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 & Newly-Renovated Third-Floor Condo w/ Amazing Water Views - Walk to Bay!1 / 17
    (16)Excellent
    1.1 kilometres 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
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    Sleek Condo w/ a Private Patio - Less than Two Blocks from the Beach/Park1 / 17
    (22)Excellent
    1.1 kilometres 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
    Sunset Cottage, Family-Friendly Oasis1 / 20
    (8)Very good
    4.3 kilometres from Old Port
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    3BR home: East End neighborhood: walk to ocean or downtown, local eateries1 / 44
    (29)Excellent
    1.1 kilometres 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
    Stunning White Water Ocean Views From This Peaks Island Home1 / 27
    (25)Very good
    4.8 kilometres 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
    3.4 kilometres from Old Port
    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
    (31)Excellent
    4.0 kilometres from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Peaks Island, Portland
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Polished, Modern Condo w/ a Balcony - Walk to Eastern Promenade & Casco Bay!1 / 18
    (55)Very good
    1.1 kilometres 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
    NEW LISTING ☼ Unique Oceanfront Home1 / 48
    (34)Excellent
    5.4 kilometres 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
    (26)Very good
    1.9 kilometres 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 Getaway In The City1 / 21
    (29)Excellent
    3.6 kilometres from Old Port
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Portland, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Adorable Portland getaway on the Eastern Promenade1 / 23
    (28)Excellent
    1.3 kilometres 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
    Fresh East End Apartment Walkable to Downtown Portland1 / 16
    (13)Excellent
    0.8 kilometres 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
    Authentic Coastal Maine Cottage Living1 / 29
    (4)Very good
    4.9 kilometres from Old Port
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    1.7 kilometres from Old Port
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    “This is the best basement apartment I have seen, wow!' This historic unique one of a kind 1600sqft boutique basement apartment in the heart of Portland is as stylish as it is cozy with exposed bricks and radiant heated floors throughout the unit. The open concept layout was beautifully conceived...
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    7.7 kilometres from Old Port
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    About this property
    Beautifully designed and updated, Private 1928, English Country style, Oceanfront Castle Estate. Featuring a seasonal heated pool: Believed to be the oldest residential swimming pool in Cape Elizabeth, Terraces overlooking sweeping lawn to the sea, private beach with a pump house (cozy building for...
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    Cape Elizabeth, Maine
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    DIRECT OCEANFRONT Perfect location1 / 28
    (12)Excellent
    5.4 kilometres from Old Port
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1.7 kilometres from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This recently remodeled open-plan living area is spacious in size and flooded with natural daylight that bounces off the beautiful cherry hardwood floor emitting radiant heat during the winter. This 1600sqft apartment was completely redone from the inside out with generous accommodations to sleep 8...
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    Portland, Maine
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    1st Floor Private Entrance Condo.  Walk to Restaurants and Parks!1 / 18
    (3)Excellent
    1.4 kilometres from Old Port
    4 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    Portland, Maine
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 12
    1.7 kilometres from Old Port
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Aged and sturdy, yet eminently modernized, this two bedroom boutique loft is perfectly situated in the heart of Portland and filled with high end amenities. From the lighting to the layout to the choice of appliances, every delightful consideration was made to compensate our guest with the best...
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Spacious 5 Bedroom, 2 Full Baths, Walkable Neighborhood1 / 29
    (13)Excellent
    3.8 kilometres from Old Port
    5 Bedrooms, 2 Bathrooms, Sleeps 20 Quick View
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    Portland, Maine
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 20
    1.7 kilometres from Old Port
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    If it isn't the ten feet ceilings or the humongous French doors complimented by the heated radiant floors or the coziness of the living space conveniently located in the center of everything that makes this remodeled apartment ideal for you, then it must be the charm of Portland ready for your...
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    Portland, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    7 Minutes to the Old Port!  Steps to the Back Cove / Ocean!  Entire Home1 / 32
    (12)Very good
    3.0 kilometres from Old Port
    5 Bedrooms, 2 Bathrooms, Sleeps 20 Quick View
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    Portland, Maine
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 20
    Stunning Waterfront House with Hot Tub1 / 40
    (12)Excellent
    3.3 kilometres from Old Port
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Portland, Maine
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
    BRAND NEW luxury penthouse condo w/ water views right in the heart of Old Port!1 / 13
    (3)Excellent
    0.3 kilometres 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
    Evergreen cottage 5' from the water1 / 17
    (13)Excellent
    5.6 kilometres from Old Port
    5 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Portland, Maine
    Holiday Rental House - 5 Bedrooms, 1 Bathroom, Sleeps 6
    Adorable Peaks Island Cottage1 / 36
    (12)Excellent
    5.2 kilometres 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
    Elegant condo w/ gas fireplace - walk to Portland's best restaurants & Old Port!1 / 21
    (19)Excellent
    0.6 kilometres 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
    Peaks Island Cottage with beautiful view of Whitehead passage1 / 32
    (16)Excellent
    4.4 kilometres from Old Port
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Portland, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.3 kilometres from Old Port
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Immerse in the tranquility of nature while allowing your comfort be seduced by this architect's successful attempt at a one of a kind custom New England cottage. Less than two minutes away from the airport and less than 6 minutes from downtown, this private neighborhood on the river offers all the...
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    Location Information
    Westbrook, Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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