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Maine Vacation Rental Homes

 NameTownBrSleeps$Range 
Located just a moment's walk to the water, enjoy scenic views of Mackerel & Lowell's Coves.

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2 Coves Bailey Island 38 $1850
This 1860 Cape has been renovated, nicely furnished, & has the most beautiful panoramic Ocean view on the Island.

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A Point of View Bailey Island 28 $1600
Quaint waterfront cottage with large deck and gorgeous views!

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Addison Red Bailey Island 25 $850
Limited Ocean view, great yard for kids, and a short walk to the beach at the end of the street.

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Anchorage Bailey Island 36 $850
Charming, two story, classic Maine cottage on Lowell's Cove. Steps to pebbly beach, a perfect spot for kayaking!

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Barnacle Orr's Island 36 $1800


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Bayview Blue Orr's Island 26 $650


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Bayview Gray Orr's Island 25 $650
Cozy ranch style home with beautiful ocean views from the front of the cottage, and coastal sunsets views from the back deck!

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Berkshire Great Island 35 $1000
A great family waterfront home with multiple decks, large yard, dock, private location, fireplace, and more!

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Bolton's Hideaway Great Island 58 $2400
Cute cottage in quiet neighborhood with beautiful sunrises and steps to Stover's Point.

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Briggs Cottage Harpswell 25 $800
Perfect location within walking distance to Cedar Beach.

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Briny Junior Bailey Island 12 $550
Perfect for a small family or couple, enjoy a large yard, water access, and beautiful sunset views.

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Camp Bullwinkle Harpswell 36 $1750
Spoil yourself in this elegant waterfront contemporary home!

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Camp Run-a-Muck Great Island 58 $4000
Charming two bedroom cottage with dock and beautiful Eastern views.

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Cottage by the Sea Great Island 26 $1300
Cute and Comfortable cottage with nice fenced in yard on waterfront with steps to shore.

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D'Amelios Cottage Bailey Island 36 $1400
Charming, newly remodeled cottage overlooking working waterfront.

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Drake Cundy's Harbor 12 $700.00
Enjoy the crashing surf from the deck of this garage apartment.

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Edgecliff Bailey Island 13 $1050
4 Season Oceanfront Home with spectacular sunrises, beautiful Bold Ocean views!

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Eider Ledge Bailey Island 47 $2300
Spacious 4 bedroom oceanfront home, beautifully decorated, perfect for entertaining, bright and fun interior, gorgeous setting!

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Faulkner Orr's Island 48 $3200
Spectacular sunset views from the wrap-around deck of this comfortable ranch.

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Gagnier's Cottage Bailey Island 26 $1200
Impressive Post & Beam waterfront home with Southwesterly views, private dock, wrap-around deck, and plenty of room for all!

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Genimatas Great Island 36 $2000
Beautiful sunsets from this upstairs studio apartment. Great affordable getaway for a couple.

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Goldsmith Apartment Bailey Island 02 $600
Year round home with Deepwater frontage on Harpswell sound. Spectacular westerly views. Gas fireplace!

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Goldsmith House Bailey Island 36 $2100
A classic Maine vacation home, this waterfront property sits right on the shoreline of Harpswell sound and includes beautiful sunset views. It features a large porch, a grand stone fireplace, three bedrooms and a loft. Great place for the Fall and Spring too.

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Gracey House Great Island 37 $1000
Enjoy the crashing surf and overview of Little Harbor at this charming cottage. The occupancy is limited to 6 max!

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Gray Rocks Bailey Island 56 $1500
Large & unique home, on the water's edge, with private dock & mooring and impressive decks to enjoy.

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Gull Perch Great Island 1 plus loft6 $2100
Cottage sits one lot back from the Ocean creating a serene location with beautiful Ocean views.

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Hamann Bailey Island 36 $950
Harbor Lights is a magnificent waterfront cottage with sweeping views of the open ocean, rugged islands, and Cundy's Harbor, a lovely fishing village.

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Harbor Lights Cundy's Harbor 36 $2000


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Haulin' Up Place Harpswell 27 $2500
Historic Cottage with views of Mackerel Cove and right of way to Little Harbor!

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Hay Bailey Island 36 $975
Must see Easterly views! Large dock to enjoy fishing and boating, sunrises, or a family BBQ! Spectacular views of the bay.

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High View Great Island 26 $2350
This 19th century stone and shingle cottage is a peaceful destination! Enjoy spectacular views to the East and West and the sounds of crashing surf.

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Inner Ledge Bailey Island 47 $3900
Turn of century cottage with crashing surf and open ocean views!

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Isle of View Bailey Island 48 $1900
A small quaint cottage with beautiful Eastern views and crashing surf. Hot Plate only - no stove.

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Jaquish South Bailey Island 02 $1000
Spectacular views of Little Harbor from the covered porch of cottage. Right of way to pebbly beach at Little Harbor!

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Lee Bailey Island 36 $1550
This pleasant year 'round cape is centrally located with a limited view of the Bay. Easy walk to water.

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Lord Bailey Island 36 $925
3 bedroom cottage with modern amenities and sweeping sunset views.

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Lubee Cottage Bailey Island 34 $1150
This cute two story cottage has beautiful sunsets and a glassed in porch. There are steps that lead down to a rocky shore front.

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McCollum Bailey Island 25 $1000
Simple, cute, and sunny at this house. Spectacular sunrises from the East side of the Island. A wrap around deck, with table and umbrella!

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Mingo Cove Bailey Island 25 $1300
Water views from every room of this beautiful year round home. Two beautiful stone fireplaces, granite counter tops, and a large deck with a outside shower!

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Morning Glory Great Island 48 $2600
Waterfront cottage at head of scenic Mackerel Cove with 2 pocket beaches (1 sandy, 1 pebbly)only 25 steps away and a shared dock. 4 complimentary lobsters delivered by local lobsterman to your dock during your stay. Also a mooring for boat upon request. Can be rented with Sea Scent and/or Sand Dollar the other Sea Forever Cottages. The Loft is not suitable for small children.

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Nautical Nest Bailey Island 24 $1300
A very cute and cozy cottage. Centrally located on the Island at the end of Steamboat Road. Shared pebbly beachfront sits just steps from the deck, beautiful westerly sunset views.

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Parciak Cottage Bailey Island 12 $850
This lovely new home is spacious, sunny, and comes with all the comforts of home. The home even has two master suites on the first floor, along with 2 gas fireplaces, 2 living rooms, a nice screened in porch, and multiple decks!

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Parciak House Bailey Island 48 $3400
Charming cottage with crashing surf and beautiful Easterly sunrise views.

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Percy's Rest Bailey Island 12 $1100
This property has over 200 feet of prime shoreline directly on Stover's Cove. It is a beautiful setting for vacationers who plan to boat, kayak, swim or relax and enjoy the scenery.

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Pletts Place Harpswell 38 $1500
Enjoy a water front deck at the dock. If you enjoy the shade, or you like to sun, this is the place. Swim from the dock, or just sit and watch the lobstermen haul their traps. Seals play on the surrounding ledges. Quiet,peaceful and with a sunset view to boot!

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Sanctuary Great Island 58 $2950
Waterfront cottage at head of scenic Mackerel Cove with 2 pocket beaches (1 sandy, 1 pebbly)only 25 steps away and a shared dock. 2 complimentary lobsters delivered by local lobsterman to your dock during your stay. Also a mooring for boat upon request. Can be rented with Sea Scent and/or Nautical Nest the other Sea Forever Cottages. The Loft is not suitable for small children.

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Sand Dollar Bailey Island 12 $990
This very sunny two story, year round house has great Ocean front. Enjoy the beautiful ocean views, wonderful sunrises and the rocky beach area right off the deck.

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Saranole Great Island 48 $1900
This quaint cottage has a great central location, with easy access to crashing surf by the Giant Staircase!

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Satterthwaite Bailey Island 47 $950
Sea Salt 1905 Vintage Seasonal Cottage - Sunrise Ocean View and Crashing Surf recent renovations, crisp and clean

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Sea Salt Bailey Island 36 $1700
Waterfront cottage at head of scenic Mackerel Cove with 2 pocket beaches (1 sandy, 1 pebbly)only 25 steps away and a shared dock. 4 complimentary lobsters delivered by local lobsterman to your dock during your stay. Also a mooring for boat upon request. Can be rented with Nautical Nest and/or Sand Dollar the other Sea Forever Cottages. The Loft is not suitable for small children.

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Sea Scent Bailey Island 24 $1400
Spectacular cottage on South end of Mackerel Cove with sunset views, two bedroom and two bath with an additional bedroom available for extra rent.

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Steamboat Landing Bailey Island 24 $1700
Charming Ranch is great for fishing and swimming. Sit on the east facing porch and watch the lobstermen haul traps, or watch as the beautiful Yachts sail by on their way to the Great Island Boat Yard just up the way!

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The Narrows Great Island 24 $1350
This sweet cottage sits on Tip-Tops hillside with views of Mackerel Cove & the Bay. One story year-round home is sunny, cozy and has a nice deck with beautiful sunset views.

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The Studio Bailey Island 25 $875
This a cozy Log Cabin is located on beautiful Mackerel Cove. The view is very limited! The cabin is surrounded by tree's, but there is a path leading down to a shared dock with owners who live nearby.

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Tip- Top Log Cabin Bailey Island 24 $775
It doesn't get any cozier than this private three bedroom Shingle Style cottage. Water on all three sides, stunning views, pebbly beach, and more!

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Tondreau Great Island 36 $2100
Victorian Era cottage with screened in porch and views of sparkling ocean.

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Tower Cottage Orr's Island 68 $1600
a beautiful place to enjoy cocktails while watching the working lobster boats, enjoying the sunrise, or simply gazing at the stars

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Tree Tops House Orr's Island 511 $2000
Cozy, newly renovated cottage has great views and water access

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Two Trees by the Sea Cundy's Harbor 24 $1400
This charming cottage is located in a great neighborhood in the Lowells Cove area. Cottage has a nice yard with swimming close by at rocky cove area. The rocky swimming area has long southeast views down the cove.

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Whalewatch Orr's Island 36 $1000
Sit in the screen porch and watch the lobster boats during the day and sunsets in the evening over the Harpswell Sound.

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White Gull Bailey Island 24 $1050
Great location almost to the end of the Island. Beautiful deck with south west ocean views, and incredible sunsets. Rocky shore front access.

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Whitesails Cottage Bailey Island 13 $650
This lovely cape with a nice yard, beautiful sunset views, and a rocky shore front.

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Whitesails House Bailey Island 47 $3500
Your Island Connection, LLC
PO Box 300 Bailey Island, ME 04003
Ph: (207) 833-7779 or (207) 833-7705 | Fax: (207) 833-7779 (call first)