Family-friendly vacation rentals in Islesboro

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Top-rated family-friendly rentals in Islesboro

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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

4.97 out of 5 average rating, 196 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 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, 399 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.

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

4.94 out of 5 average rating, 108 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, 152 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.

Top guest favorite

A spacious bedroom is illuminated by natural light from two skylights and a large window. A queen-sized bed is positioned with bedside tables featuring lamps on each side. A comfortable chair is placed in the corner, accompanied by a round area rug on the floor.

Guesthouse in Lincolnville

4.98 out of 5 average rating, 194 reviews

Peaceful Suite - Hiking, Beach, Nature

Welcome to the “East Wing”! The complete apartment is new: salt box style with beautiful views of nature (hummingbirds, fireflies, starry skies). The East Wing is first to greet the sun in the morning. Enjoy your coffee on the private deck, or sip wine at night by the fire pit. Close to Tanglewood Rd (4H camp) , Camden Hills State Park trails, and Lincolnville Beach(1 -2 miles). The area is quiet- yet just a few miles away from shopping and restaurants in Camden, Belfast, & Rockland.

Top guest favorite

A charming blue cottage is set in a lush green landscape, surrounded by trees and colorful flower beds. A brick chimney rises from the home's side. In the foreground, a cluster of large stones is visible on the well-kept lawn.

Guesthouse in Orland

4.99 out of 5 average rating, 177 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Top guest favorite

A two-story red building features a sloped roof with solar panels, surrounded by lush greenery. An outdoor area includes a picnic table and several chairs, offering a tranquil space for relaxation. A garage door can be seen, blending seamlessly with the rustic aesthetic.

Apartment in Belfast

4.98 out of 5 average rating, 339 reviews

Room with a Brew

Welcome to our new building. "A Room With a Brew" is located above Belfast's newest craft brewery, Frosty Bottom Brewing. A small community supported brewery open 2 days/week for 3-4 hours for beer share members. Guests can request a tour of the brewery and sample some fresh beer. Owners live in downtown Belfast and are available should any issues arise during your stay. The apartment/brewery is located 3 miles from downtown on a quiet road that offers local hiking and biking.

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, 172 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 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 Maine

5 out of 5 average rating, 127 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

4.92 out of 5 average rating, 245 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

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, 168 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

The coastal home is set back from a tree-lined driveway, surrounded by lush greenery. A spacious lawn leads to the house, which features a sloped roof and a large circular window, framed by Maine's vibrant flora.

Chalet in Lincolnville

4.99 out of 5 average rating, 155 reviews

Charming home near ocean & close to Camden/Belfast

Cozy coastal home within walking distance of Ducktrap Beach in Lincolnville. Enjoy a relaxing stay at our house situated on 5 private acres of wooded trails, 1/3 mile from a public beach. Private location with spacious deck and open yard, bordered by a meandering stream, beautiful Maine pine trees, wild flowers and ferns. 15 minutes to Camden or Belfast & 1.5 hours to Acadia National Park.