Family-friendly vacation rentals in Bailey Island

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Top-rated family-friendly rentals in Bailey Island

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

The rustic cabin exterior features a steep gabled roof and wooden siding, surrounded by trees. Windows are symmetrically placed, allowing natural light to enter. The entrance, with a panel door, invites guests into a quiet retreat set in a secluded woodland area.

Farm stay in Brunswick

4.97 out of 5 average rating, 128 reviews

Cozy, Rustic Cabin on a Small Organic Farm

This little cabin in the woods is a wonderful place to get away from it all. Tucked away in the back fields of our farm, hidden in the trees, you’ll love the cozy bed in the loft and privacy. It is a rustic, comfortable experience. No running water or electricity; we supply plenty of water and battery powered lanterns for you. The outhouse is close to the cabin, an outdoor shower near the farmhouse. Fresh organic sheets, wool blankets and linen down comforter make for a great sleeping place

Guest favorite

A cozy living area features a queen-sized futon covered in a light throw, set on wide-plank wood floors. A colorful area rug lies under a glass coffee table. Tall bookshelf walls house various books, and natural light is welcomed through skylights.

Guest suite in Brunswick

4.88 out of 5 average rating, 121 reviews

Private guest suite in historic Maine cottage

Come enjoy a relaxing stay in the upstairs of a cozy, historic home nestled on the beautiful coast of Maine. The house is within a 2 minute walking distance from Simpson's Point where you can enjoy swimming, picnics, sunsets, and stargazing. You can expect peaceful, quiet days and evenings with the option to bathe in a skylight-lit bathtub/shower and snuggle up in comfy beds lit by twinkle lights. Rental includes entire upper floor with private entrance along with tv/internet (Netflix only).

Top guest favorite

A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.

Cottage in Brunswick

5 out of 5 average rating, 182 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Guest favorite

Four wooden lounge chairs are arranged around a small table on a grassy lawn, overlooking a rocky shoreline. The calm ocean stretches into the distance, framed by a clear sky with soft clouds.

Home in Harpswell

4.95 out of 5 average rating, 136 reviews

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

Top guest favorite

A spacious dome tent is nestled among tall trees, with sunlight filtering through the leaves, creating a warm glow. The forest floor is covered with soft earth and scattered leaves, enhancing the natural surroundings, while the calm ambiance invites visitors to relax and enjoy the scenery.

Island in Monmouth

4.98 out of 5 average rating, 250 reviews

Hammock Haven Island Dome

The Hammock Haven Island Dome looks at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite meals, hammock nap on a dock in the water, bask in the glow of the fire or wood stove, hear the calls of the loons, play on the rope swing, canoe, kayak, or paddle board the lake, explore the trails of this 14 acre wooded island, and then repeat as needed. We greet you at our shoreside dock and help you settle into island-life. Enjoy super clean, Superhost, Maine Guide hospitality.

Top guest favorite

A tiny house with a grey exterior sits nestled among lush greenery and colorful flower beds. It features tall windows that allow natural light to flow in, and a bright red door that adds a pop of color. Surrounding steps made of stones lead up to the entrance.

Tiny home in Durham

4.99 out of 5 average rating, 357 reviews

Crow’s Nest Tiny House at Old Crow Ranch

The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.

Top guest favorite

A wooden deck leads to the entrance of the yurt, featuring two green Adirondack chairs flanking the doors. The surroundings are wooded, with a carpet of forest floor visible and trees providing a natural backdrop.

Yurt in Chebeague Island

4.98 out of 5 average rating, 166 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Water. Outdoor fire pit. WiFi . Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

Guest favorite

An airy cabin interior features wood beams and a large sliding glass door, providing access to a deck and surrounding greenery. A small dining area with a table and two chairs is visible alongside a well-equipped kitchen area, complete with modern appliances.

Tiny home in Bowdoinham

4.91 out of 5 average rating, 132 reviews

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

Guest favorite

The exterior of the multi-unit house is shown, featuring a light gray facade and a red roof. An expansive wooden deck is visible on the second level, overlooking the green lawn. Bright flowers adorn the entrance, adding a touch of color to the outdoor space.

Apartment in Orr's Island

4.94 out of 5 average rating, 103 reviews

Shore House, Leona Unit - Ocean Front Property

This is the ground level of a multi-unit house. It is wheelchair friendly, with cathedral ceilings, a modern kitchen, and wide plank pine floors. The expansive deck will only enhance you experience overlooking a working wharf on Garrison Cove and Casco Bay. Dogs allowed upon approval. Must not be big barkers and owners are responsible for any waste. We want to be courteous with all renters and their pets. Weekly rentals preferred in July and August months (Saturday - Saturday)

Guest favorite

The two elevated structures of the tree dwelling are connected by a rope bridge, surrounded by lush green trees. Natural materials are utilized in the design, which includes a balcony and multiple levels that create a unique, inviting silhouette against the forest backdrop.

Treehouse in Georgetown

4.98 out of 5 average rating, 445 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Guest favorite

The studio's interior displays rustic charm with original rough-hewn beams overhead. A spacious bed is visible in the back area, while a comfortable seating arrangement and TV are situated in the front. Natural light streams through multiple windows, enhancing the welcoming atmosphere.

Guesthouse in Harpswell

4.95 out of 5 average rating, 471 reviews

Harpswell Studio on Waterview Property! Lobster!

Cottage Style Studio! Clean, spacious, colorful, comfy, bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Popham Beach and Reid State Park with expansive beaches are 35 minutes or less away. Enjoy the trails in the woods with spectacular views or walk on the beach at one of the state parks! So beautiful!

Guest favorite

A cozy living area features a comfortable gray sofa arranged near a light wooden coffee table. A large TV displays a streaming service, while natural light enters through expansive windows adorned with soft curtains. A small kitchenette is visible in the background.

Guesthouse in Brunswick

4.92 out of 5 average rating, 171 reviews

Modern Brunswick Tiny Home near Bowdoin & Downtown

A lofted bed space with additional optional pull out couch fitted with ergonomic foam mattresses. This space has air conditioning as well as heat and amazing natural light. Brand new bathroom with rain shower head! A full kitchen with mini fridge, separate freezer space, oven, stove and coffee/tea supplies. Centrally located in Brunswick, and quiet! Right across from Bowdoin’s Whittier Field, and 10 minute walk to Maine Street.