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$25,094 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
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, 132 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.

Indoor spacesFamilyCheck-in

Top guest favorite
A spacious sleeping area features a king-sized bed adorned with patterned bedding and accent pillows. Natural wood beams and a warm wood ceiling create an inviting atmosphere. Sunlight enters through a large window, illuminating a comfortable corner chair and a small side table.
Apartment in Northport
4.96 out of 5 average rating, 135 reviews

Off-Grid Oasis with Ocean Views, Near Rt. 1

Take in the ocean views from our quiet hilltop just 20 minutes from downtown Camden and 10 minutes from Belfast. This newly constructed above garage studio apartment is private, full of light, and effortlessly off-grid. The studio features a king-sized bed, table and chairs, comfy chair and bean bag, as well as a full bath. The patio area gives breathtaking views of the bay and island. A perfect oasis amid sight seeing! We also offer $20 back for multi-night stays. Please message for details.

Indoor spacesKitchenNearby

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, 209 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.

KitchenIndoor spacesTV

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
5.0 out of 5 average rating, 112 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.

FamilyIndoor spacesAmenities

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.

FamilyIndoor spacesGetting around

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

KitchenFamilyPets

Top 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.

Indoor spacesKitchenComfort

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
5.0 out of 5 average rating, 106 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.

KitchenIndoor spacesWalkability

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, 266 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.

FamilyKitchenBiking

Top guest favorite
Cabin in Georgetown
5.0 out of 5 average rating, 205 reviews

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit

Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart & separated by a privacy screen and natural landscaping.

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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).

KitchenIndoor spacesParks

Top guest favorite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 452 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Indoor spacesKitchenView

Popular amenities for Islesboro family-friendly rentals

When is the best time to visit Islesboro?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$64,616 GYDG$62,316 GYDG$62,734 GYDG$61,689 GYDG$41,823 GYDG$62,734 GYDG$71,308 GYDG$67,962 GYDG$62,734 GYDG$62,734 GYDG$61,689 GYDG$62,734 GYD
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