Island holiday rentals in Maine

Broom Island

Broom Island – Your Private Island Getaway Escape to Broom Island, a secluded 18-acre retreat in the heart of North Haven & Vinalhaven, offering total privacy and natural beauty. Stay in a rustic off-grid solar cottage, explore scenic trails, or kayak around the island and Mill River. Enjoy the private dock, guest mooring, and access to the island's rental or charter boats for nearby adventures, trips to town or wildlife watching. Perfect for a quiet, nature-filled escape or outdoor adventure.

Trailside Tent on private island w/ historic fort

Set within the 16-acre grounds of civil war-era Fort Scammel, FORTLAND is a 7-site, one-of-a-kind island campground. Space to roam, 3 beaches for island guests only, a fort to explore, and breathtaking views in every direction of the Casco Bay islands and the beautiful Portland skyline. Birds & butterflies abound on this shining example of the unique beauty of the Maine coastline. Parking & boat transport included in cost of your stay! [Note: More transport details can be found on our website]

Walden: Private Island Cabin!

Escape to Serenity: Lakeside Cabin on a Private 24-Acre Island near Jackman, Maine Discover the ultimate retreat on our secluded island, nestled just outside Jackman, Maine. Our lakeside cabin offers a perfect blend of comfort and nature, providing an ideal setting to unplug and rejuvenate. Complimentary Boat Rental: Explore the pristine lake at your own pace with our included boat rental. Come experience the tranquil beauty of our lakeside cabin and make memories that will last a lifetime.

Cabin in Paradise

Beautiful quiet and private cabin on Frye Island. Access Frye island via a 9 car ferry that runs every 15-30 minutes. Close to Portland. A beautiful 9 hole golf course with bar and grill, 15 public beaches, 2 marinas, a general store,restaurant, tennis courts, a pool, ball field, basketball court, and endless trails and roads to explore. Take bike rides to the store, catch frogs, fish for bass, play ball, and hang out at the beach! Our Bikes are included for with week long rentals.

Charlottesville: Private Island!

Welcome to our cozy Charlottesville cabin! As you step inside, you'll immediately find two comfortable twin beds ready for a restful night's sleep. The cabin is equipped with a heater to keep you warm and cozy, along with reliable Wi-Fi so you can stay connected. You'll also have access to a full bathroom with hot water, ensuring a refreshing and comfortable experience. With electricity throughout, you'll have all the modern conveniences you need for a relaxing stay.

Waterfront Island Maine Getaway

Escape to a timeless retreat on the Mill River in Penobscot Bay. This family-owned home of 40+ years blends rustic elegance with modern comforts: soaring windows, Hartwood pine floors, exposed rafters, and two wood-burning fireplaces. Outdoors, enjoy four decks, sweeping sunset views, a lawn for games, and a private dock for boating or kayaking. With a fully stocked kitchen and unique personal touches, this home is as warm and welcoming as it is unforgettable.

Vintage ISLAND farmhouse, BYO boat/kayak. Unique!

A Midcoast Maine island paradise. Bring (or rent) your boat/kayak and taste for adventure. Secluded circa-1850 saltwater farmhouse, 1/4-mile private shore. No plumbing (outhouse, rain-barrel showers). No electricity (candles, lamps, flashlights; solar phone-charging). One mile from Friendship Harbor town landing. Beach, wharf, boathouse, forest trails, blueberries, kayak adventures, dark night skies, lobsters, peace, quiet. Note: Inaccessible at dead-low tide.

Eagle's Nest on 8 acres next little john preserve

Nestled on 8 acres overlooking Casco Bay, the Eagle's Nest cottage has 1 bedroom and 1 bathroom. Open plan with full-kitchen and living room including a queen-size sofa bed. Located on an island, you're only 20 minutes from downtown Portland and 10 minutes from downtown Yarmouth. Last but not least the cottage is a 5-minute walk from a 23-acre preserve that has numerous scenic viewpoints, tide pools and ledges, and picnic tables. Coastal Maine at its best!

Island Tree House: Lake Front, Kayaks, & Fire Pit

The Oaktagon Tree House is what happens when you decide to live with the forest instead of just visiting it. Built around a living red oak (her name is Annie), this octagonal tree house invites you up into the canopy, where birds provide the soundtrack and the lake glimmers below. Perched on a 14-acre island just a half-mile from shore, it’s a place to slow down, look outward through leaves and branches, and remember what it feels like to be held by trees.

Island Cottage Getaway in Casco Bay!!

Log cabin includes a master bedroom, loft w/4 beds & a small room with bunkbeds. It has solar power, a bathroom/hot shower, kitchen, dining room, den, living room, & a big private yard. It's close to the Portland airport, close to 5 star restaurants, and is on the outskirts of a beautiful harbor. There are only a few other cabins and no roads on the island. Island fun such as fishing, swimming, camping and exploring will keep you busy for your stay.

Flagstaff Lakefront-Near Sugarloaf Vacation Home

Large, comfortable four season home on Flagstaff Lake, facing Sugarloaf & Bigelow Preserve Mountains. Three acres of land on dead-end road with private waterfront access, gazebo, firepit & dock on Flagstaff Lake. Canoe, kayak, swim and fish, all from property. Beautiful views of Lake & nearby mountains throughout the house. This 3 bed/2 bath gem is a great house for both single and multi-families!

Naughty Dog Private Island Log Cabin

Naughty Dog Island is what happens when island time meets unapologetic canine freedom. This is a private island log cabin where you and your pup can truly be away away — no leashes once you arrive, no neighbors, no schedules worth keeping. Just you, your dog(s), and a 1,400-acre lake that becomes your shared backyard. If your dog has ever dreamed of running the show, this is their moment.