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South Freeport Vacation Rentals

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    Don't let other travelers get your favorite South Freeport area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 27 Rentals in South Freeport
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    South Freeport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    South Freeport
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    The following rentals are within 10 miles of South Freeport.
    Colorful wonderful Penthouse Apartment1 / 17
    (2)Very good
    Brunswick
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Yarmouth
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Patio
    • Grill
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to this beautiful Yarmouth vacation rental house, nestled among a scenic backdrop of tall pines on Maine's picturesque coast. Located on 2 acres of private tidal front property in the town of Yarmouth, this inviting home can comfortably accommodate up to 6 guests among its 3 bedrooms and 2...
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    Yarmouth, Maine 04096
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dramatic Oceanfront Home on Casco Bay1 / 21
    (1)Excellent
    Freeport
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Central Heating
    • Cable/satellite TV
    • Ocean Views
    • Waterfront
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 18, 2016
    The pictures of this home attracted our attention, and they are exactly what you will find. Then there is more. Betsy and Gar have created a vacation home that appeals on many...
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    About this property
    Sunrise or moonrise, it's your choice! Sip your coffee or wine while you sit on the patio of this spectacular waterfront home. You will be treated to an ever-changing natural drama from this recently built home on Flying Point overlooking Casco Bay. Herons, gulls, and other sea birds share the...
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    Freeport, Maine 04032
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Bailey Island
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Internet Access
    • Private Yard
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this picturesque Bailey Island setting on 2.06 acres and 199’ frontage on Maine’s rocky coast. Completely renovated in 2006-07 this Shingle Style oceanfront home possesses superior craftsmanship inside & out overlooking Casco Bay. Feel free to contact us with any questions....
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    Bailey Island, Maine 04003
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Long Island
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    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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    Long Island, Maine 04109
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Oceanfront Cottage in Freeport1 / 23
    (1)Excellent
    Freeport
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • DVD Player
    • Patio
    • Private Yard
    • Wi-Fi
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 28, 2017
    We just returned from this awesome home. There were 6 in our party a family affair ages from 40-81. There was an awesome view of ocean, great location, and plenty of shopping if...
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    About this property
    This charming four bedroom cottage features 350’ of unobstructed ocean views toward Casco Bay and the islands, located just 5 miles from Freeport's hundreds of outlet stores and restaurants, and just 30 minutes from Portland. The cottage is set just 75 feet from the shoreline, with ocean views...
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    Location Information
    Freeport, Maine 04032
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Freeport
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Grill
    • Patio
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW: Sweeping Ocean Views from Three Suites, Private Swimming Cove and Dock. Available for weekly rentals (Sun-Sun) in summer and fall and 3+ day rentals off-season. Gather your family and friends for an authentic Maine vacation to remember. This gorgeous country home sits on 1,000+ feet of...
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    Freeport, Maine 04032
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    Freeport
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Grill
    • Washer
    • Patio
    • Central Heating
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright and spacious, comfortable home offers sweeping ocean views from nearly every window. Two master bedrooms at opposite ends of the house makes it ideal for two couples - with or without children. Set on a beautiful, forested 5 acre lot near one of Maine's most popular state parks, and...
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    Location Information
    Freeport, Maine 04032
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Yarmouth
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated fully-furnished 1,000 square-foot apartment with new wood floors and dishwasher, all-utilities included, washer and dryer in building, off-street parking, in owner-occupied two-family home, walking distance to bakery, restaurants, grocer, riverfront walking trail, harbor. Quiet...
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    Yarmouth, Maine 04096
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Yarmouth
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of Yarmouth, Mill Reach offers the perfect setting for a great holiday, with off-street parking for one car. Relax in the modern open plan living, kitchen and dining area which is furnished to a high standard throughout. The living area leads out onto the private decking area perfect...
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    Yarmouth, Maine PO40 1TW
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Shepard's Sea Side Cottage1 / 18
    (6)Excellent
    Freeport
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Central Heating
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 12, 2014
    This "cottage" is so perfect! Comfortable, spacious and the ocean views are spectacular. Casco bay is right outside your windows. Darlene was excellent to work with...
    Reviewed December 17, 2013
    This is one of the most beautiful places we've ever been! Even in the dead of winter - sub zero temps outside right now - you could not find anywhere nicer. We are...
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    About this property
    A vacation for all and something for all to do! You name it this house has it all - LOCATION -For gazing at sunrises and sunsets (2 porches and water on two sides!) -For kayaking and canoeing at your back door (canoe, kayak and life vests included) -For renowned shopping at L.L. Bean and...
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    Location Information
    Freeport, Maine 04032
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Bailey Island
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Patio
    • Cable/satellite TV
    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Restored oceanfront 1910 shingle-style house with private pool, spa, private beach, and incomparable views in all directions. Six bedrooms, four full baths, two fireplaces, large updated kitchen and oceanside porch. This house has all its original charm and authentic details including natural...
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    Location Information
    Bailey Island, Maine 04003
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Orrs Island
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Ocean Views
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is close to the beautiful water with an amazing ocean view from our front patio and walking access. With westerly views over Harpswell Sound enjoy the sunsets with Mt. Washington in the back ground on a clear night. The cottage is bright and cheery with a great deck that overlooks the...
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    Location Information
    Orrs Island, Maine 04066
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Bailey Island
    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Central Heating
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The historic Captain York House has been on Bailey Island for more than 100 years. It has expanded into a 7 bedroom, 6.5 bathroom house that can accommodate families, large groups and family reunions. This house provides a great home base for exploring Bailey Island and the surrounding coastal...
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    Location Information
    Bailey Island, Maine 04003
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    Falmouth
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Housekeeping Included
    • Central Heating
    • Ocean Views
    • Waterfront
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please note: Our checkin time is 3pm and checkout is 11am, but we can often accommodate other arrangements! Andy's Retreat is a comfortable, spacious and convenient home-base to relax and explore Portland & Coastal Maine. We're located right off Exit 53 of the Maine Turnpike, just 15 minutes...
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    Falmouth, Maine 04105
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Long Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/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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    Long Island, Maine 04109
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Freeport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For those on the go, you will be minutes to Freeport's shopping and dinning district. Bradbury Mountain or Wolfe's Neck State Park for enjoying the outdoors with views to Casco Bay and the Harraseeket River, is another 10 minutes away. If you have a flexible schedule, head south to Portland and the...
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    Freeport, Maine 04032
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Yarmouth
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Wi-Fi
    • Central Heating
    • Private Yard
    • DVD Player
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cleaves Street Loft is all newly renovated with stainless appliances, brand new butcher block counter tops & tableware's. The loft boasts it's own private balcony and spacious bathroom with radiant stone floors and heated walk in tile shower. This space is located in the heart of Yarmouth...
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    Location Information
    Yarmouth, Maine 04096
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Falmouth
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adorable, quaint and ideally located Maine Beach cottage. Fully furnished with updated furniture, comfortable beds, and all the necessary amenities. Steps from private beach - bring your kayak, paddleboard or other water craft or just relax and watch the sailboats on the Bay and go fishing from the...
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    Falmouth, Maine 04105
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Falmouth Foreside Maine Contemporary Cottage Home - indoor lap pool, roof deck1 / 29
    (1)Terrible
    Falmouth
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Indoor Pool
    • Washer
    • Wi-Fi
    • Central Heating
    • Hot Tub
    • DVD Player
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5+ Bedrooms, 3 Full Baths Sleeps 10-14 Just up the hill from one of the largest mooring harbors on the East Coast, and across the street from Maine's most famous General Store is this newly completed property designed and built by one of New England's up and coming Architects. Featuring and...
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    Falmouth, Maine 04105
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Falmouth
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Washer
    • Balcony
    • Terrace
    • Ocean Views
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large, spacious, home on National Register allows plenty of room for guests to socialize inside and out. Walking distance to Portland Yacht Club, Handy Boat launch, town dock facility, walking trails, town beach, Town Landing Market, and Dockside Restaurant. Short drive to Freeport shopping and...
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    Falmouth, Maine 04105
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Secluded, waterfront deckhouse with panoramic view1 / 6
    (7)Very good
    Brunswick
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Central Heating
    • DVD Player
    • Ocean Views
    • Internet Access
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set back on a ledge, this spacious, contemporary home looks out through pine and birch on panoramic views of Maquoit Bay. Newly renovated kitchen, dining room, living room and den areas open onto large deck, 125 feet from the shore. Three bedrooms and study all have water views. Enjoy quiet...
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    Brunswick, Mid Coast Maine 04011
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Freeport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • Waterfront
    • Parking
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning water views await at this 1BR cottage situated mere minutes from downtown Freeport shopping and dining. Launch a kayak from your backyard, dine al fresco on the oceanfront deck, and spend quiet evenings by the wood-burning fireplace. Traveling with a larger group? Reserve this cottage...
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    Location Information
    Freeport, Maine 04032
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Freeport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Washer
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This brand-new 3BR/3BA, coastal-inspired waterfront home features an open-concept living area with a wood-burning fireplace and a modern kitchen with fun retro-style appliances. An upper-level patio offers views of the water, and the lower-level family room has a multi-game table with pool, air...
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    Freeport, Maine 04032
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Brunswick
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunny special second floor one bedroom apartment filled with light and colors. Lovely queen bedroom; living room with 6 south facing windows; dining room; full kitchen; private entrance; quiet yet close to everything. Walk to town, restaurants, the college, art galleries, and all amenities. Drive...
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    Location Information
    Brunswick, Mid Coast Maine 04011
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    South Freeport Flight and Weather Info
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    Portland Intl Jetport
    15.6 miles from South Freeport
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