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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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, 406 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 guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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
4.95 out of 5 average rating, 113 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.

Top guest favorite
Tiny home in Surry
4.96 out of 5 average rating, 164 reviews

Tiny House at Wooded Bliss Homestead

On the edge of our family homestead overlooking meadow & forest, this tiny house offers a quiet, cozy refuge only 40 minutes from Acadia National Park. There's a twin daybed on the ground floor & a double futon in the loft. Full kitchen & tiny bathroom with shower too. A heat pump keeps the place toasty warm or nice and cool. The tiny house and meadow are very private on the edge of the property, and just for you. Our family's gazebo, fire pit, hammock, trail & garden are shared with guests.

Guest favorite
A cozy interior features a bed with a striped blanket and wooden floorboards. A small dining table with two chairs is positioned near glass doors that open to a view of the hills. Natural light fills the space, complemented by sheer curtains.
Cabin in Union
4.82 out of 5 average rating, 130 reviews

Drift Cottage near the coast

This simplistic cottage sits atop a blueberry hill in Union Maine. Sit and enjoy a fire and view of the hills. It's only a 3 minute walk to groceries, pizza, Cafe, and The Sterlingtown restaurant, with outdoor seating and live music! or get take out and enjoy the outdoor Asian inspired dining area for an unforgettable night! perfect overnight spot on the way to Acadia! 1.5 hours away. 15 minutes to Owls Head, Camden, Rockland. Perfect cental spot for day trips to the prettiest of Maine!

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
4.95 out of 5 average rating, 111 reviews

Little Apple Cabin on 5 acres, amazing stargazing!

Cabins don't come much cuter than Little Apple Cabin. It's as if someone stayed here and *then* invented the word 'CabinCore'. Nestled in the magical woods of Midcoast, Maine, this cabin is the perfect getaway. Located just 25 minutes from the coast, it's the perfect spot for exploring all that the midcoast has to offer. 20 minutes to Camden and Rockland, 25 minutes to Belfast. (No hunting allowed). Surround yourself by the forest, stargaze all night, and rejuvenate in nature.

Top guest favorite
A charming yellow house features white trim and a welcoming front door. Flower boxes are filled with vibrant blooms beneath the windows, surrounded by a neatly tended garden. A stone wall provides a defined border, enhancing the inviting exterior.
Guest suite in Rockland
4.98 out of 5 average rating, 467 reviews

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. *SHARED wall between studio and main house, therefore some shared noise. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOG

Top guest favorite
A view from a shaded patio showcases a round table surrounded by wicker chairs. The lush green lawn extends to the water's edge, where trees provide a natural frame for the serene expanse of the bay, dotted with clouds reflecting in the distance.
Home in Belfast
4.92 out of 5 average rating, 188 reviews

Belfast Ocean Breeze

Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal town of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, and boasting breathtaking views of Penobscot Bay and beyond. The exceptional grounds offer an ideal setting for relaxation with the added allure of explorations along the shoreline or tennis/ pickleball at park/ year round hot tub. Near downtown and Rt. 1. No parties.

Top guest favorite
A serene cabin interior features a king-sized bed adorned with a textured blanket and decorative pillows. Natural wood paneling and a woven wall hanging create a warm ambiance. A small wooden table stands beside the bed, complemented by a comfortable seating area with a woven chair.
Cabin in Northport
4.95 out of 5 average rating, 100 reviews

The Birch Bark Cabin

Completely unplug at this silent and stunning off-the-grid cabin situated in the heart of mid coast Maine. Minutes from several lakes, ponds and Penobscot Bay. Total privacy in the woods, private fire pit, tidy composting toilet and LED lighting. Propane stove and fresh water included. Sun shower available upon request. King sized bed is made up with sheets, blanket and down comforter. Private parking and red flyer wagon provided to carry in your gear - 200 foot path to cabin.

Top guest favorite
The exterior of the cottage features a large screened-in porch framed by tall trees. A pathway leads to the entrance, while colorful shrubs and a pumpkin add seasonal charm. The serene waters of the Sheepscot River are visible in the background.
Cottage in Edgecomb
4.98 out of 5 average rating, 330 reviews

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Top guest favorite
Three colorful flower pots are displayed on a blue wooden surface. The left pot features pink flowers, the middle pot has yellow blossoms, and the right pot showcases soft peach-colored blooms. Lush greenery can be seen in the background, creating a serene outdoor setting.
Apartment in Searsmont
4.98 out of 5 average rating, 173 reviews

Searsmont Studio

Fight inflation with a reasonably priced Maine vacation. Low prices, excellent value. Check our ratings. Peak Foliage Oct. 14-20 Entire studio efficiency apartment w/ private entrance above our garage. Fully furnished, including washer and dryer. Country setting on quiet road. Starlink High Speed WiFi/Satellite TV, full kitchen. gardens, lawns and picnic table. Close to Camden, Rockport and Belfast, but in the country.

Top guest favorite
A well-lit studio space includes a set of large windows allowing natural light to filter in. A small kitchenette featuring a coffee maker and a mini fridge is visible. Comfortable seating is provided by two armchairs paired with a table, and a door leads outside.
Guesthouse in Rockport
4.91 out of 5 average rating, 146 reviews

Peaceful Guesthouse in Rockport

This peaceful studio guesthouse has everything you need for your Rockport/Camden trip. The unit comes with Wi-Fi, free parking, and laptop-friendly workspace. During your stay, you can enjoy your private studio with kitchenette. Within close proximity to Camden (3 Miles) and Rockland (6 Miles.) Rockport Harbor (1 mile walk) features several popular restaurants, coffee shops, and beaches. An ideal base to explore Rockport.

Top 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
4.95 out of 5 average rating, 843 reviews

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

Popular amenities for Islesboro family-friendly rentals

When is the best time to visit Islesboro?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$52,214 GYDG$52,214 GYDG$52,214 GYDG$57,435 GYDG$57,226 GYDG$65,998 GYDG$71,220 GYDG$67,878 GYDG$62,657 GYDG$52,214 GYDG$52,214 GYDG$48,037 GYD
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Quick stats about vacation rentals that are family-friendly in Islesboro

  • Total vacation rentals

    Explore 140 vacation rentals in Islesboro

  • Nightly prices starting at

    Islesboro vacation rentals start at G$16,708 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,440 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

    140 of Islesboro vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Islesboro rentals

  • 4.8 Average rating

    Islesboro stays are highly rated by guests—averaging 4.8 out of 5!