Family-friendly holiday rentals in Islesboro

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 800 Mbs fiber 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. We’re very pet friendly!

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.

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

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.

Private Sauna+Near Beach+FirePit+Forest View+Pond

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat & Backup Automatic Generator * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin 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 and separated by a privacy screen and natural landscaping.

Quaint Oceanfront Island Cottage, off Bar Harbor

Feel the stress melt away at Barnacle Hall, a peaceful, romantic getaway w/ stunning water views, just steps to the sea. This snug & welcoming cottage is tucked away in tranquil Burnt Coat Harbor, with its own private rocky beach and a bluff with radiant Maine island sunsets. Truly unwind, stepping into a by-gone era in this quaint cottage, w/ a charming stone fireplace w/ woodstove. Rustic-feeling, with full services. Families welcome! Wifi now available. [NOTE: Not a great option for Acadia]

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.

Bayview House 1br 2ba Stunning Harbor Views

Do you crave balmy summer evenings or frosty winter days that make you feel like you've been transported back to a simpler time? Or long for days spent on the water or experiencing village life with friendly locals in charming pubs tasting local eats? Experience the simple joys of life with rustic yet modern amenities offered at this coastal 2-story home. Whether daily strolls by the water or taking in the sunset on your deck, you'll fall in love with this lovely New England destination.

Eco-friendly studio - ocean views, close to beach

Sunny eco-friendly cottage on Route 1, steps from the beach! A cozy studio with a Murphy bed, a full bath, and kitchenette - stovetop, fridge, toaster, & microwave. Beautiful views of Penobscot Bay – don't worry, the blinds will keep the sunshine at bay when you need a nap! You're within easy walking distance of sandy beaches, restaurants, shops, a coffee roaster, and a market. Explore nearby hiking trails, Mount Battie, and the charming towns of Belfast, Camden, Rockport, and Rockland.

Acadia Treehouse near Bar Harbor - Private Luxury

Escape to a secluded luxury treehouse in the forest of Maine. Unwind in the spa-like full bath with a jacuzzi and sauna. Includes 1 bedroom and loft with 2 queen beds, full kitchen, fireplace, 2 screened porches & outdoor shower. Perfectly located for visiting Acadia National Park, ATV trails and scenic drives. Whether soaking in the jacuzzi, relaxing by the fire, or unwinding on the porch to the sound of rustling leaves, this luxury treehouse is a getaway you’ll never forget

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private 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.

The Loft. A Midcoast Maine Home Base.

A perfect place to use as your base for exploring Midcoast Maine. We are 8 miles from Camden or Rockland. 34 miles from Boothbay Harbor and 90 miles from Bar Harbor. This is your home away from home. A fully stocked kitchen, ready for meals after a long day of exploring. We have 1.5 baths, a washer and dryer and three Smart Tv’s. This 1700 sq foot warehouse loft has central air conditioning, two bedrooms and a large living space.