
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.

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.

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.

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.

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!

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.

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

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.

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.

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.

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.

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.

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
Family-friendly home rentals with a hot tub

Raven's Crossing - Kate's Cottage

Lovely new loft in permaculture gardens

Tiny A-Frame Romantic Getaway

Modern Cabin in the Pines • Hot Tub + Near Acadia

Secluded Retreat w/ Luxe Hot Tub & Forest Views

The Seamist Cottage - Converted Historic Barn

Cozy 3BR Acadia Hideaway w/ Hot Tub & Fire pit

Hot Tub Time Machine
Family- and pet-friendly home rentals

Glenview Lane Cabin

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

Blue Life Farm

Camp Ottah' Knot Rustic Camping Cabin 2

Peaceful & private waterfront cabin

"The Lair" Guesthouse

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

The Maine Getaway - Lakefront with Beach
Family-friendly home rentals with a pool

Deluxe Cabin A at Wild Acadia

Cozy Studio Flat, Belgrade Lakes Region

The Jarvis Homestead | Historic Maine Mansion

Luxe Liberty: Getaway with Heated Indoor Pool!

Coastal Retreat with Pool and Cheerful Vibes

Park Place in the Heart of Bar Harbor

Loon Sound Cottage, On the Water

Ocean View Retreat with Heated Pool / Hot Tub
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$52,214 GYD | G$52,214 GYD | G$52,214 GYD | G$57,435 GYD | G$57,226 GYD | G$65,998 GYD | G$71,220 GYD | G$67,878 GYD | G$62,657 GYD | G$52,214 GYD | G$52,214 GYD | G$48,037 GYD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 13°C | 18°C | 21°C | 20°C | 16°C | 9°C | 3°C | -3°C |
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!
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- Family-friendly rentals Waldo County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Acadia National Park
- Pemaquid Beach
- Northeast Harbour Golf Club
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Acadia National Park Pond
- Hermon Mountain Ski Area
- Dragonfly Farm & Winery
- Sandy Point Beach
- Bear Island Beach
- Sand Beach
- Lighthouse Beach
- Eaton Mountain Ski Resort
- The Camden Snow Bowl
- Kebo Valley Golf Club
- Spragues Beach
- Wadsworth Cove Beach
- Farnsworth Art Museum
- Narrow Place Beach
- Rockland Breakwater Light
- Driftwood Beach
- Islesboro Town Beach
- Three Island Beach
- North Point Beach




