Family-friendly vacation rentals in Islesboro

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Islesboro

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

0 of 0 items showing

1 of 3 pages

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, 381 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

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, 346 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

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, 165 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, 111 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!

Guest favorite

Cottage in Belfast

4.87 out of 5 average rating, 203 reviews

Eastside Garden Cottage - 5-mins From Town

This happy home has all you need for a perfect Maine vacation or remote work escape. Relax in the garden, hang out on the deck, soak in the clawfoot tub, enjoy the fast wifi – or walk or drive over to Belfast center - it's close! This coastal town is truly a gem, but if you’d like to explore further afield, it’s also an excellent base for day trips to Camden (30 minutes) or Acadia National Park (1.25 hours.) Belfast celebrates diversity. We welcome guests from all backgrounds.

Guest favorite

A cozy studio apartment features a wood-paneled interior with a spacious seating area, including a vibrant red sofa adorned with patterned cushions. A kitchen with green accents and white appliances is visible, along with a dining table and large windows allowing natural light to brighten the space.

Guesthouse in Lincolnville

4.93 out of 5 average rating, 141 reviews

Ocean View Beach Loft Carriage House Lincolnville

This charming spot overlooking the bay is laid back and welcoming. Fully furnished, including linens, basic beach supplies —towels, chairs and umbrella. There is wi-fi and a Roku TV included (you will need your own streaming accounts), an air conditioner, and balcony with a view of Penobscot Bay. We strive to be an allergen free space so do not allow animals. We use all essential oil natural products (bleach disinfectant where needed) and natural laundry soap for our linens.

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, 437 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!).

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, 101 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, 133 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).

Superhost

The exterior of a historic farmhouse is presented, showcasing a large white building with multiple gabled roofs. Lush green grass surrounds the home, while colorful flower beds add a vibrant touch. A welcoming porch features steps leading to the entrance, framed by leafy trees.

Apartment in Brooksville

4.83 out of 5 average rating, 140 reviews

Tapley Farm Waterfront Apartment, Acadia, Pets

Private Beach on Historic Waterfront farm with cozy, private apartment for two. In remote, quintessential Maine style, gaze at breathtaking sunsets over private beaches. Queen bed, full kitchen, full bath and 5G await. Stunning open fields with fireflies and star-filled skies and the saltwater air lulls you to sleep. Antique charm and complete modern comfort and privacy. Experience the real Maine on a Sea Captain Farm. Acadia National Park, Castine. Dog OK $30 per day

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.