Family-friendly vacation rentals in Islesboro

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Top-rated family-friendly rentals in Islesboro

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

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Guest favorite

The exterior of the cottage features a light gray shingle facade, complemented by white trim around the windows and front door. A set of three windows with flower boxes is situated on each side of the door. A welcoming porch leads to the entrance.

Home in Rockland

4.95 out of 5 average rating, 379 reviews

Downtown-Walk to All Things Rockland

Cute, convenient, and clean recently renovated 1930’s cottage has two bedrooms, sleeps 4, a private backyard, and is within walking distance to downtown, restaurants, nightlife, co-op & supermarket, museums, shops, art galleries, Harbor Park, ferry and the waterfront. Enjoy off-street parking and an ocean view with the sun glistening off the harbor at the end of the street. This is a perfect home-base for a coastal Maine vacation and festivals. Discounts offered for weekly and monthly stays!

Guest favorite

An aerial view captures a contemporary house nestled amidst vibrant autumn foliage alongside a calm bay. The lush green lawn leads to a shoreline with smooth water, while walking pathways and a stone patio can be seen in the garden, integrating seamlessly into the natural landscape.

Home in Trenton

4.93 out of 5 average rating, 287 reviews

Acadia National Park ocean front & garden cottages

Both our houses are designed in the contemporary style. We used custom made decor and cherry tree furniture. A lot of windows, glass doors, bright and open space are inside the house. It is very quiet outside. You most likely will be alone at the beach. We share the whole sea cove with only one neighboring house. It is a pure paradise if you want to live on the beach on your own and within minutes of driving to the main local attractions. You'll be amazed of our botanical garden and landscape.

Guest favorite

A bright living area features two modern white chairs and a low coffee table set atop a colorful area rug with floral patterns. Large windows allow natural light to illuminate the space, showcasing a tranquil view of the surrounding greenery.

Guest suite in Rockport

4.92 out of 5 average rating, 224 reviews

Charming Harbor Private One Bedroom

Situated just above a stream just off Rockport Harbor, this quiet, small one-bedroom apartment has its own private entrance and small deck. Located on the back side of RAYR wine and cheese shop, this charming apartment is within a 10-minute walk of two wonderful restaurants in the village of Rockport, 18 Central and Nina June, as well as a lunch spot and a deli. A wonderful getaway space for couples and solo adventurers, you’ll love it because of the location, ambiance, privacy and charm.

Top guest favorite

A spiral staircase crafted from natural wood ascends to a loft area, featuring rounded steps that maintain the organic shape of the wood. A window nearby offers natural light, illuminating bookshelves filled with various volumes and a map hanging on the wall.

Cabin in Hope

4.98 out of 5 average rating, 345 reviews

Hand built cabin overlooking a pond

Beautiful hand built cabin, overlooking Cotton Pond. Ten minutes from Camden, the sailing mecca of the east coast. Solar lights, (we are off the grid) gravity fed kitchen water, gas-hot water outdoor shower, outhouse overlooking the forest. Hiking trails everywhere! Swimming across the road on Hobbs Pond. If you book in November, there is a possibility that if it gets cold, you will not have a hot outdoor shower and will use water from a 5 gallon ceramic container for drinking and cooking.

Top guest favorite

A view of a quiet street in downtown Belfast is captured, featuring brick buildings and shops. A tree provides greenery, while parked cars line the road. The sky is bright with a few clouds, and the waterfront is visible in the distance, enhancing the lively atmosphere.

Apartment in Belfast

4.97 out of 5 average rating, 381 reviews

Belfast Harbor Loft

Come and experience the peaceful, yet vibrant, atmosphere of Belfast! This downtown loft is a great place to stay, being just two blocks away from the beach. Enjoy the morning light in the two bedrooms, both facing the harbor, while the living room offers a stunning view of Main Street. The loft is full of character, with its refurbished floors, exposed brick and rafters, large windows, and newly renovated kitchen and bathroom. Make yourself at home in a calm and inviting atmosphere.

Top guest favorite

The cottage, a contemporary black structure, is nestled within lush green fields and surrounded by trees. A gravel parking area is visible to the right, with a vehicle parked nearby. A cozy outdoor seating area can be seen in front of the cottage.

Cottage in Owls Head

4.99 out of 5 average rating, 164 reviews

Coastal Maine contemporary cottage

Our cottage is meant to be both contemporary and rustic. It is where we go to get away from the hustle and bustle of the modern world and slow down. There is no TV or internet, even our phone is an old rotary one. You will see that we have a good radio, and games and books to read, and plenty of things to do outside. We hope you will take the time at our cottage to comfortably reconnect with yourself, and each other, while enjoying what Maine is renowned for, our quality of life.

Top guest favorite

A houseboat floats gently on the calm waters of Lake Pemaquid, surrounded by lush greenery on the hillsides. The vessel features large windows, a spacious deck, and a vibrant red and cream exterior, reflecting the tranquil ambiance of the natural setting.

Houseboat in Bremen

5 out of 5 average rating, 108 reviews

Houseboat ROAM on Lake Pemaquid, Mid Coast Maine

- A Little Closer To Nowhere - A one-of-a-kind eco-travel experience, ROAM is a simple - but comfortably equipped - houseboat that can accommodate two guests. Homeported on Lake Pemaquid in Bremen, Maine, you will seamlessly integrate into your surroundings while enjoying visiting loons, sweeping sunsets, and clear northern air. ROAM (& her brother NOMAD) are offered in conjunction with the exclusive Otyokwa Lakeside Cabins - please inquire if you'd like to add a land option!

Top guest favorite

The spacious living area features large windows offering natural light and views of the surrounding greenery. A comfortable seating arrangement includes a patterned sofa and armchair, while a wooden coffee table occupies the center. A dining area is positioned nearby, complemented by a stylish console table.

Apartment in Northport

4.97 out of 5 average rating, 99 reviews

Maine Alpaca Experience A Maine Coast Get Away

This beautiful open and spacious two bedroom apartment is nestled in the perfect location on Route 1 between Belfast and Lincolnville close to Camden, Rockland and on the way to Acadia National Park. It's ideal for couples, solo adventurers, business travelers, and families. Whether it's business, hiking, the beach, dining, shopping or all of the above, this beautiful full apartment allows you all the comforts of home. Guest must be 21 years of age to book. No pets please.

Top guest favorite

A screened porch offers a view of Penobscot Bay, featuring two green wicker chairs adorned with floral cushions. The scenery includes a lush lawn and Adirondack chairs positioned for relaxation, with water visible in the background and distant hills framing the horizon.

Cottage in Belfast

4.99 out of 5 average rating, 130 reviews

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

Guest favorite

A charming cabin is set amidst greenery, featuring a sloped roof and wood siding. The front porch is equipped with two blue chairs, inviting relaxation. A gravel pathway leads to the entrance, surrounded by grass and small plants.

Cottage in Penobscot

4.82 out of 5 average rating, 104 reviews

Cozy cottage in the woods

Cozy cabin set in the woods surrounded by fields. The perfect place for a romantic getaway, or to reconnect with friends and family, unplug and relax. Get cozy by the wood stove on chilly nights, or star gaze while you make s’mores by the fire-pit. Our place is just a few minutes drive to the ocean and great hiking trails. We are located very close to historic Castine and Maine Maritime Academy, and about one hours drive from Acadia National Park.

Superhost

A vibrant red house is nestled in a wide field of tall grass, surrounded by dense greenery. Solar panels are installed on the roof, reflecting the sun's rays. A clear blue sky with scattered clouds provides a bright backdrop to this peaceful setting.

Home in Belfast

4.9 out of 5 average rating, 111 reviews

The Strawberry House

Passive house certified and winner of Leed project of the year, the Strawberry House (named by our daughter) has huge windows looking onto a field of milkweed and wildflowers. The property is 4 acres and very private; the road is walled off by a thick border of foliage. Behind us is only woods and there are miles of lovely nature trails accessed from the bottom of our field. It's only a 2 mile drive to the center of town Enjoy!

Guest favorite

The bedroom features a queen-size bed with a white bedspread, complemented by antique furnishings. Natural light filters through two windows adorned with sheer curtains. A cozy armchair is positioned beside a small table, while artwork decorates the walls, enhancing the room's classic charm.

Home in Camden

4.88 out of 5 average rating, 170 reviews

Intown Camden, 2 bedroom, 2nd floor, own entrance

Restaurants, shopping, and the harbor are a five-minute walk from one of the oldest capes in Camden village. House was built in 1800 on a quiet one-way street. The second-floor apartment has a private entrance and includes one bedroom with a queen-size bed, and a sitting room with a single bed, a seating area, t.v, . Wifi access. Private outside garden with own entrance. Minimum 3 night stay - 10% off for full week stays.