Family-friendly vacation rentals in Islesboro

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Islesboro

  • Total vacation rentals

    Explore 160 vacation rentals in Islesboro

  • Nightly prices starting at

    Islesboro vacation rentals start at G$25,113 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,560 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Islesboro vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Islesboro rentals

  • 4.9 Average rating

    Islesboro stays are highly rated by guests—averaging 4.9 out of 5!

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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Top guest favorite
A charming modern cottage with a red exterior and a pitched roof stands amidst lush greenery. The covered porch is furnished with comfortable seating, inviting relaxation. Large windows allow natural light to enter, enhancing the welcoming atmosphere of the property.
Home in Northport
4.98 out of 5 average rating, 266 reviews

Cute Midcoast Cottage w Hot Tub

Kick back and relax in this ideally located modern cottage. Enjoy a soak in the hot tub or the peace of the covered porch. Situated in the heart of midcoast Maine, this cottage has it all. An elegant kitchen that awaits your culinary delights, a spacious living area, a primary bedroom with a TV, a kingsize bed and a luxurious bath with a soaking tub and a walk-in rainfall shower, plus twin bunk beds for the kiddos. A small store and a farm to table restaurant are conveniently across the street.

Top guest favorite
The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.
Home in Georgetown
4.99 out of 5 average rating, 134 reviews

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Top guest favorite
The image captures a serene view of the water at sunset, with the sun reflecting on the surface. Framed by lush green foliage, a small rustic bench is positioned on the shore, inviting quiet moments of contemplation.
Cottage in Belfast
4.98 out of 5 average rating, 211 reviews

Quiet cottage on the bay

Settle in at this mid-coast Maine treasure, where you will find more than you hoped for in a getaway. Located in a private neighborhood and setback on a private road on 2.5 acres. You can take a short stroll down a wooded path to the Belfast bay and watch the sunset or simply enjoy the view from living room. The rocky beach gives you access to a wonderful piece of the Maine coastline. Come make some memories at this unique, pet and family-friendly quiet cottage just 1 mile to downtown Belfast.

Top guest favorite
The cabin is nestled among lush greenery, featuring a modern wooden exterior with multiple windows. Elevated on stilts, it harmonizes with the natural surroundings of ferns and trees, allowing for a serene atmosphere in a tranquil forest setting.
Cabin in Sedgwick
5 out of 5 average rating, 113 reviews

The Cabins at Currier Landing Cabin 2: Meadow

Tranquil cabin; open plan. Bedroom w/queen bed & privacy doors. Alcove w/bunkbeds. The Cabins at Currier Landing, featured in Dwell as “Three Magical Tiny Cabins Take Root in a Maine Forest,” are located on the Thos. Currier Saltwater Farm. Glimpses of water & access to 300’ of the Benjamin River Harbor shore. 2 seasonal cabins; 1 studio cabin. Centrally located on the Blue Hill Peninsula near Deer Isle, the cabins offer access to outdoor activities, cultural events, restaurants & shops.

Top guest favorite
Cabin in Hope
4.98 out of 5 average rating, 376 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
Cabin in Sedgwick
4.98 out of 5 average rating, 191 reviews

Rustic Chic Private Getaway Cabin @Diagonair

Pet-friendly Maine cabin on 12 private acres of woods and blueberry fields, 1 hour to Acadia National Park. A favorite of couples visiting Maine for the first time. • 15 minutes to shopping, hiking, swimming • Open kitchen and sitting room with new appliances and gas fireplace • Screened porch with rocking chairs and chaise • Loft bedroom with full bed and new linens • WiFi, Roku TV, gas grill, stocked bar • EV charger • Seasonal wild blueberries • Dark skies, slow mornings, quiet nights

Guest favorite
Two Adirondack chairs are positioned on a grassy area in front of a small cabin with a green metal roof. Lush greenery surrounds the cabin, providing a serene and natural setting.
Guesthouse in Lincolnville
4.97 out of 5 average rating, 476 reviews

"The Lair" Guesthouse

"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee from 8 am to 4 pm everyday! We are closed for Winter, will re-open Mid-April. Thank you.

Top guest favorite
A charming single-story cottage is surrounded by a lush green lawn. Large windows allow for ample natural light, and flower beds with colorful blooms adorn the entrance. A serene landscape with distant hills completes the tranquil scene under a partly cloudy sky.
Cottage in Lincolnville
5 out of 5 average rating, 107 reviews

Sunny 2 Bedroom cottage - Walk to the beach!

Single story cottage in the heart of Midcoast Maine! This 2 bedroom cottage is in the Lincolnville Beach area. Located within eyesight and walking distance of the public beach, the Islesboro Ferry terminal, McLaughlin’s restaurant, and the Beach Store. Property is located on US route 1- just 6 miles north of Camden (8 minute drive), and less than 15 minutes south of Belfast. This year-round cottage provides a lovely retreat for resting while exploring all the Midcoast has to offer.

Top guest favorite
The exterior of a contemporary yurt is illuminated at night, set among trees in a wooded area. The structure features a circular design with a central roof vent and a wrap-around deck. Soft lighting highlights seating areas on the porch.
Yurt in Appleton
4.95 out of 5 average rating, 345 reviews

SILVER MOON, a Yurt for All Seasons

Silver Moon at The Appleton Retreat is quite private, check out the Trail Map. This contemporary yurt features a private therapeutic hot tub on the wrap around deck, a fire pit, and fast wifi. Silver Moon is located in a wooded area close to a bog that attracts a variety of wildlife. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Top guest favorite
A newly constructed cottage is nestled among trees, featuring a screened porch with wooden rocking chairs. The entrance is defined by a bright red door, inviting guests to enjoy the surrounding natural beauty. Gravel pathways lead to the entry, with a lawn area visible.
Cottage in Lincolnville
5 out of 5 average rating, 132 reviews

Rocky Top Hideaway with level 2 charging station.

Feel the magic in this quiet secluded hillside retreat. Awaken your senses with the smell of the salt air, pines and an occasional whiff of coffee beans roasting all while watching the ferry go back and forth to Ilesboro. Early risers will enjoy spectacular sunrises. Experience nature without being too far off the beaten path. A private half mile walk down the driveway will end at brick sidewalks leading you to Lincolnville Beach, one of Maine's stretches of sandy shoreline.

Guest favorite
A spacious white tipi is nestled among trees, with a clear view of a quiet lake. A picnic table sits nearby, accompanied by a hammock stretched between two trees, inviting relaxation in this serene natural setting.
Tent in Brooks
4.91 out of 5 average rating, 268 reviews

Waterfront Tipi Glamping // Phoenix Landing

Majestic private waterfront Tipi * on a lake. Quiet nature oasis with hot tub, woodstove, firepit, modern grill, and all the essentials. Ice skate or xc-ski across the frozen lake and watch the bald eagles fly overhead, or relax in the Adirondack chairs in front of the bonfire while you make smores and cook dinner on the grill or over the open fire, then snuggle up inside the tipi while you listen to vintage vinyl and let the owls hoot you to sleep. *Tipi closed March-April.

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, 171 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).

Popular amenities for Islesboro family-friendly rentals

When is the best time to visit Islesboro?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$64,666 GYDG$62,364 GYDG$62,782 GYDG$61,736 GYDG$41,855 GYDG$62,782 GYDG$71,362 GYDG$68,014 GYDG$62,782 GYDG$62,782 GYDG$61,736 GYDG$62,782 GYD
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