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Peaks Island Holiday Homes

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    All 37 Rentals in Peaks Island
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    3 BR 1.5 BA COTTAGE WITH WATER VIEWS OF CASCO BAY1 / 13
    (1)Average
    Popular9 views in the past week
    Peaks Island
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Peaks Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Peaks Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Peaks Island
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    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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    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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    Peaks Island, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Peaks Island
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    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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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    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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    Peaks Island
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    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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    The following rentals are within 10 kilometres of Peaks Island.
    Dog-friendly home with a game room and patio, close to parks, trails & downtown!1 / 24
    (1)Excellent
    Popular50 views in the past week
    Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • 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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    Portland, ME - East End Garden Suite1 / 12
    (2)Average
    Popular41 views in the past week
    Portland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Shared Garden
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    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 04102
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Portland
    4 Bedrooms, 2 Bathrooms, Sleeps 17 Quick View
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    • Terrace
    • Grill
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    • Balcony
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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 04106
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 17
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    Welcome to the Skybox!! Now renting for July!1 / 19
    (2)Average
    Popular53 views in the past week
    Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Terrace
    • Waterfront
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    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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    Portland, Maine 04101
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Portland, Maine - East End Rental1 / 44
    (26)Very good
    Popular143 views in the past week
    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 1 week 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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    Portland
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Balcony
    • Air Conditioning
    • 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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    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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    • Satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    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...
    Reviewed 28 October 2016
    We stayed here for five days and thoroughly enjoyed our time at this place. Awesome house in a great neighborhood close to many restaurants and other activities. Marilys was...
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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 04106
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Portland
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Private Garden
    • Wi-Fi
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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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    Portland, Maine 04103
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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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
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    • Ocean Views
    • Balcony
    • Satellite TV
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My home is brand new and was completed at the end of the Summer in 2015. I designed and furnished the home with a lot of thought, attention to detail and aesthetic appeal. Floors are hardwood and Carrara marble in two baths and Brazilian black slate in the half bath. There are 3 bedrooms and 2...
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    South Portland, Maine 04106
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    • Wi-Fi
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    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2016
    The apartment is well equipped and clean and has a real beach house feeling even when its not on the beach. The hosts are very friendly and helpful.
    Reviewed 10 August 2016
    tastefully done up flat in the upper floor (owners live ground floor). Nice , helpfull hosts. Basic food stuff for breakfast .... provided ( coffee, sugar.....), very clean
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    About this property
    Minimal And Clean - Ready For Travellers This second floor apartment - with its two bedrooms, one bathroom, kitchen, and more - offers plenty of space for up to four guests. Minimal, clean, and carefully appointed with traveller necessities. Guests have access to two off street parking spots, all...
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    South Portland, Maine 04106
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Portland
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    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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    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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    South Portland
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Terrace
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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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    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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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
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    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
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
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    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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    Long Island
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Nicely appointed with 4 levels of living space. This home is nicely decorated and furnished with an updated kitchen, butlers pantry with wine cooler, 2 porches, bedrooms and full baths on every level, master bedroom suite, and 3rd floor has an open bunk room, sitting area, and a full bath…ideal...
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    Long Island, Maine
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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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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    Portland, Maine 04102
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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    Location Information
    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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    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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    Location Information
    South Portland, Maine 04016
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Long Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Maine island cottage with lots of charm. The home was recently painted a light grey with white trim.This rental home offers an open floor plan with nice deck off the back. The floors and walls are all knotty pine offering a great cottage feel. This 3 bedroom, 2 bath home offers a master bedroom...
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    Long 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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    Location Information
    Portland, Maine 04101
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Long Island
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Nicely furnished patio home is a great vacation spot! This home offers 3 bedrooms, 1 1/2 baths and sleeps 5. It offers upscale furnishings, beautiful original artwork on the walls, and newly installed hardwood floors on the first level. Internet, Satellite & Apple TV and a Sonos sound system with...
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    Location Information
    Long Island, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Portland
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Parking
    • Washer
    • Grill
    • Wi-Fi
    Suitability
    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
    • Washer
    • Patio
    Suitability
    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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    Long Island
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Internet Access
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wake each morning to a beautiful Maine sunrise from this gorgeous 4 bedroom (1 king, 1 queen, 2 full, 2 full plus twin) 2 1/2 bath home. This is just the place to spend your Diamond Cove vacation! Sunrise Cottage is over 3000 sq ft, sleeps 8, and is located in a prime location in sight of the ferry...
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    Location Information
    Long Island, Maine
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Long Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Firebarn is a charming free standing home in a great location; close to the pool, walkway to the General Store, dock, marina & ferry. It is a 2 bedroom home with large loft that sleeps 6-8. The home is equipped with internet & Apple TV. All of our homes are completely furnished and fully...
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    Location Information
    Long Island, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Long Island
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    End unit townhouse with beautiful wooded views. Offers 3 bedrooms, 1.5 baths, impressive hand crafted wood floors throughout, and a wood burning stove. Enjoy cooking in this updated kitchen with granite counter tops, stainless steel appliances, and custom built cabinetry. A finished basement offers...
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    Location Information
    Long Island, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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