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Family-friendly vacation rentals in Islesboro

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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$25,106 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 cozy seating area features a dark sofa adorned with decorative pillows, positioned near large windows allowing natural light. A small black and red checkered blanket is draped over a wooden bench. A vintage trunk and a black gas fireplace complete the inviting space.
Apartment in Belfast

Gothic Victorian Carriage House Apartment

This newly renovated carriage house was the original hayloft of the Gilkey House, a historic American Gothic Victorian built in 1879 by the renowned architect George Harding. Unique, private & luxurious, this 2 bdrm apartment is filled with designer touches. Bright & spacious living area is perfect for families & friends to gather, cook & create memories that will last a lifetime. Walk to the best restaurants and shops, the Farmer's Market, Oceanfront Harbor, trails, Front St. Shipyard & Marina.

KitchenFamilyQuiet

4.95 out of 5 average rating, 388 reviews
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

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.

FamilyKitchenAmenities

4.98 out of 5 average rating, 282 reviews
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

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.

KitchenIndoor spacesNearby

4.96 out of 5 average rating, 157 reviews
Guest favorite
A cozy living space is featured, showcasing a brown leather chair with a plaid throw. A rustic wooden coffee table sits in front of a cast-iron stove. A staircase with dark wooden railing leads to the upper level, while a modern kitchen is visible in the background.
Home in Belfast

Historic Stephenson Farm on 35 acre Mason Pond

This water front historic Stephenson Farmhouse is a cozy 3 bedroom farmhouse that sits on 5 acres with frontage on Lower Mason Pond. A bird lovers paradise along with sightings of beaver & river otters. Trail from house leads to waterfront, canoes, paddles & PFD’s and a picnic table. We’ve maintained the antiquity of the house along with many antique pieces of furniture. Enjoy amazing sunsets, expand your birding life list, pick apples and blueberries in season. . . on a nature preserve.

KitchenIndoor spacesHeating

4.92 out of 5 average rating, 125 reviews
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

"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.

KitchenIndoor spacesParks

4.97 out of 5 average rating, 491 reviews
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

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 spacesBackyard

4.99 out of 5 average rating, 117 reviews
Top guest favorite
A cottage is positioned near the water's edge, surrounded by trees. Outdoor seating in the form of Adirondack chairs is visible, offering a view of the ocean. Steps lead from the door to the grassy area, which features a barbecue grill.
Cottage in Rockport

Cottages at Oakland Seashore (Cottage #8)

Nestled on 70 acres of oceanfront property in Rockport, Maine, the cottages at Oakland Seashore are the perfect choice for a romantic getaway, vacation with friends, or a family gathering. Formerly the Oakland Seashore Motel & Cabins, I recently purchased the property and have decided to rent a few of the cottages this summer and fall on a weekly basis. Reminiscent of a bygone era, these cottages are simple and provisioned with the basics, but have the most remarkable ocean views.

FamilyKitchenDecor

4.95 out of 5 average rating, 106 reviews
Top guest favorite
A scenic view captures a grassy area leading to a dock over Hobb's Pond. Four red Adirondack chairs are arranged around a fire pit made of stones. A mountain rises in the background, framed by fluffy clouds in a blue sky.
Cabin in Hope

Hobb’s House - Year Round Log Cabin on the Water

Cozy 2 Beds, 1 pullout sofa bed, 2 Bedroom, 2 Bath Log Cabin with water/mountain views on Hobb’s Pond. Relax on the dock, grill, canoe (1)/kayaks (2)/swim during the day and relax with your streaming services on the smart TV at night. 5min drive to the Camden Snow Bowl for ski/snowboard during the winter. Ice skate on the pond. Rent out a boat during your stay. 13 min drive to downtown Camden for great restaurants and a sunset cruise on a sailboat. Close proximity to hiking trails!

Indoor spacesKitchenLaundry

4.97 out of 5 average rating, 140 reviews
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

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).

Indoor spacesKitchenWifi

4.99 out of 5 average rating, 181 reviews
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

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.

KitchenIndoor spacesCondition

4.97 out of 5 average rating, 464 reviews
Top guest favorite
An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.
Cottage in South Thomaston

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

FamilyKitchenWalkability

4.96 out of 5 average rating, 216 reviews
Guest favorite
A vibrant sunset is reflected on the calm waters of Graham Lake, with streaks of orange, pink, and purple filling the sky. Silhouettes of distant hills and trees frame the scene, creating a serene atmosphere perfect for relaxation.
Cottage in Waltham

Quiet lakefront cottage on Graham Lake

Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets

KitchenIndoor spacesHospitality

4.94 out of 5 average rating, 921 reviews

Popular amenities for Islesboro family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A serene deck area features two wooden chairs and a small table overlooking a lush green lawn and tranquil water. The peaceful view includes trees framing the shoreline, offering a calming ambiance and connection to nature.
Home in Belfast

[Trending Now]Belfast City Park Ocean House

Indoor spacesKitchenGetting around

4.93 out of 5 average rating, 259 reviews
Top guest favorite
The exterior of a cozy cabin is showcased, featuring wooden shingles and a dark roof. A small deck includes a two-chair dining set and a hot tub nearby, surrounded by lush greenery and a well-maintained lawn.
Cabin in Searsmont

Birch Hill Cabin w/Hot Tub

KitchenFamilyBathroom

4.99 out of 5 average rating, 247 reviews
Top guest favorite
A modern cabin is set against a backdrop of tall pine trees, featuring large windows that invite natural light. The exterior showcases a wooden deck with a seating area, complemented by a staircase leading to the entrance.
Cabin in Penobscot

Modern Cabin in the Pines • Hot Tub + Near Acadia

FamilyIndoor spacesQuiet

4.97 out of 5 average rating, 191 reviews
Top guest favorite
A two-story post and beam house is set on a spacious green lawn, surrounded by trees and autumn foliage. The exterior features wooden siding with multiple windows, showcasing a blend of rustic charm and natural beauty.
Home in Swans Island

Hot Tub Time Machine

Indoor spacesKitchenLocation

4.95 out of 5 average rating, 327 reviews
Guest favorite
A hot tub is situated outdoors amidst a serene wooded setting, surrounded by trees with the faint hint of steam rising. The structure features a partially enclosed wooden fence for privacy, with a few nearby seating options visible, set against a softly lit twilight sky.
Cottage in Deer Isle

Beachfront Guest Cottage - Year-round Hot Tub!

FamilyKitchenBeach

4.93 out of 5 average rating, 434 reviews
Guest favorite
The tree dwelling is elevated among sturdy trees, featuring a wraparound balcony surrounded by foliage. Large windows invite natural light, offering views of the lush surroundings. A rope bridge connects to another elevated structure, enhancing the unique treehouse experience.
Treehouse in Georgetown

Modern Treehouse w/Water Views+Cedar Hot Tub

KitchenIndoor spacesAir conditioning

4.98 out of 5 average rating, 468 reviews
Top guest favorite
The cabin's exterior features a colorful mural along one side, complemented by large windows. A spacious deck is furnished with black rocking chairs and a small table, surrounded by natural landscaping and gravel pathways.
Cabin in Lamoine

Unique, Whimsical Off-Grid Cabin

Indoor spacesFamilyLayout

4.97 out of 5 average rating, 304 reviews
Guest favorite
A hot tub bubbling gently is positioned on lush green grass, with a serene view of Lake Saint George in the background. Colorful autumn trees line the water's edge, and a clear blue sky adds to the tranquil setting.
Home in Liberty

Modern Lakefront Home w/ Hot Tub • Summer Vacation

FamilyKitchenValue

4.87 out of 5 average rating, 122 reviews

Family- and pet-friendly home rentals

Top guest favorite
Apartment in Belfast

Belfast Harbor Loft | Downtown

KitchenFamilyBiking

4.96 out of 5 average rating, 432 reviews
Guest favorite
A cozy living area features a grey sectional sofa adorned with yellow pillows. A blue coffee table sits in front, topped with decorative items and magazines. Light flows in through sheer curtains, while a kitchenette is partially visible in the background.
Guesthouse in Camden

Superb Location w/EV Hk up & Walk to town & ocean

Indoor spacesFamilyAmenities

4.92 out of 5 average rating, 274 reviews
Top guest favorite
A charming log cabin nestled among lush greenery, featuring a sloped roof and multiple windows. A picnic table is positioned in front, surrounded by natural landscaping. The peaceful outdoor setting invites relaxation and exploration in the surrounding forest.
Cabin in Boothbay

Simple Boothbay Log Cabin on Water

FamilyIndoor spacesOutdoor spaces

4.94 out of 5 average rating, 505 reviews
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

Quiet cottage on the bay

FamilyKitchenGetting around

4.98 out of 5 average rating, 219 reviews
Top guest favorite
A calm cove surrounded by dense green trees reflects serene water. A sailboat gently floats on the bay, complemented by soft rock formations emerging from the water's surface. Sunlight brightens the landscape, casting a tranquil atmosphere over the scene.
Home in Stonington

Blue Arches: waterfront vacation home on 18+ acres

KitchenIndoor spacesHeating

4.95 out of 5 average rating, 175 reviews
Guest favorite
A charming cottage exterior is framed by lush green grass and shrubs. A stone pathway leads to the entrance, while the sky above features soft clouds, suggesting a warm day. The cottage is adorned with wood shingles and large windows, providing a welcoming appeal.
Cottage in Deer Isle

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

KitchenFamilyDecor

4.89 out of 5 average rating, 166 reviews
Top guest favorite
A modern cabin exterior showcases a deep blue facade and a welcoming entry, highlighted by a wooden deck adorned with an outdoor seating area. The surrounding landscape features various plants and autumn decor, enhancing the serene setting within the woods.
Tiny home in Appleton

Little Apple Cabin on 5 acres, amazing stargazing!

Indoor spacesKitchenLayout

4.95 out of 5 average rating, 148 reviews
Guest favorite
Home in Stonington

Bayview House 1br 2ba Stunning Harbor Views

Indoor spacesKitchenAmenities

4.93 out of 5 average rating, 124 reviews

Family-friendly home rentals with a pool

Guest favorite
Home in South Thomaston

Large private area, close to Rockland

Indoor spacesFamilyBathroom

4.94 out of 5 average rating, 117 reviews
Guest favorite
Home in Bangor

Cozy, fun, 3 bedroom home with a pool and Hot Tub.

FamilyKitchenTV

4.97 out of 5 average rating, 372 reviews
Guest favorite
The house is set on a grassy hill, surrounded by neatly trimmed bushes and rocks. A welcoming porched area wraps around the front, and the roof features dormer windows. The backdrop consists of a clear blue sky with scattered clouds, creating an inviting atmosphere.
Home in Belfast

Gorgeous house with a view

KitchenFamilyOutdoor spaces

5.0 out of 5 average rating, 46 reviews
Guest favorite
Cottage in Belfast

Oceanfront Shore Cottage - Newly Renovated

FamilyKitchenAccuracy

4.84 out of 5 average rating, 44 reviews
Superhost
The living area presents a blend of comfort and style, featuring a spacious gray sofa complemented by a wooden coffee table. A stone fireplace serves as a focal point, while built-in shelves display curated items. Natural light fills the space through large windows, enhancing the inviting ambiance.
Home in Lincolnville

Coastal Retreat with Pool and Cheerful Vibes

KitchenFamilyLong stay

4.86 out of 5 average rating, 22 reviews
Superhost
An in-ground pool is surrounded by a concrete deck, featuring a roofed area with three bar stools. Lush greenery lines the perimeter, ensuring a private and peaceful environment. The clear blue water is inviting, ideal for summer relaxation and recreation.
Home in Tremont

Large MDI house w/pool perfect for groups+families

FamilyIndoor spacesValue

4.71 out of 5 average rating, 51 reviews
Guest favorite
Cabin in Orland

Camping Cabin

FamilyOutdoor spacesCondition

5.0 out of 5 average rating, 9 reviews
Guest favorite
An in-ground pool is framed by a spacious deck, featuring lounge chairs and seating areas. Surrounding greenery provides a sense of privacy. A light-colored exterior of the house can be seen in the background, contributing to the relaxing ambiance of the outdoor space.
Home in Rockport

Dog Friendly Midcoast Cape

Indoor spacesFamilyCondition

4.95 out of 5 average rating, 73 reviews

When is the best time to visit Islesboro?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$64,649 GYDG$62,347 GYDG$62,766 GYDG$61,720 GYDG$41,844 GYDG$62,766 GYDG$71,344 GYDG$67,996 GYDG$62,766 GYDG$62,766 GYDG$61,720 GYDG$62,766 GYD
Avg. temp-7°C-6°C-1°C6°C13°C18°C21°C20°C16°C9°C3°C-3°C

Destinations to explore