Island holiday rentals in Maine

A Once in a Lifetime Oceanfront Escape

Escape to an exclusive oceanfront retreat on a secluded Maine peninsula, surrounded by white sand beaches and rocky coastline. Just a short ferry ride from Portland, this hidden gem feels like you’ve arrived at the edge of the world. Immerse yourself in expansive views that seem plucked from the pages of a travel magazine. Explore pristine beaches, vibrant waters, or relax on expansive decks with this once in a lifetime experience that blends seclusion, natural beauty, and unforgettable vistas!

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.

Hammock Haven Island Dome

The Hammock Haven Island Dome looks at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite meals, hammock nap on a dock in the water, bask in the glow of the fire or wood stove, hear the calls of the loons, play on the rope swing, canoe, kayak, or paddle board the lake, and explore the trails of this 14 acre wooded island, and then repeat as needed. We greet you at our shoreside dock and help you settle into island-life. Enjoy super clean, Superhost, Maine Guide hospitality.

8 Ferry Road - The House that Ships Built

This historic house sits on a small rise within approximately 7 acres of mostly forested land. It is a 2-minute walk from Mackerel Cove, which is just about the finest place to be a sunset spectator on Swan's Island; it also happens to be the place from which the ferry comes and goes 3 to 7 times a day. At 8 Ferry Road, you are about a 1/2 mile stroll from the ferry dock and close to Atlantic Road which leads to an abundance of other stops, landmarks, and trailheads to adventure. Come visit!

Sealport Cottage: Full week Saturday-Saturday only

Sealport Ocean Cottage is a magical place with sparkly days and starry nights! Beautiful ocean views of Seal Cove, Blue Hill Bay on the "Quietside" of this island. Rustic, family owned for 60+ years, this comfy, quiet summer only cottage is all yours to enjoy sunsets, days on the porch, woods and seashore near Acadia National Park. Weekly rentals Saturday to Saturdays only: check-in 4pm or later, check-out 10am, with 5 safety hours between guests for professional cleanings, relax & enjoy!

Isle Be Back!

This quintessential Island New Englander is ready to welcome you. Well stocked with toys and equipment for hours of fun. Dog friendly too! Sit on the front porch and enjoy the well groomed perennial gardens, relax while cooking out on the large back deck, explore the beaches, eat fresh lobster, gaze at the stars, enjoy and decompress 23 miles out to sea. Must travel to island by air or sea; travel fees not included in reservation. Once your visit has concluded you'll say "Isle" Be Back!

The Stilt House

Once the island Trading Post (in the 1820's) now serves as a private retreat on Westport Island. The whole property has been listed on the National Register of Historic Places since 1982. The building is nestled at the water's edge, half on land and half on stilts over the tidal waters of the Sheepscot River. The property has its own private deck, island, rocky beach, trails and hammock. This is an old structure - over 200 years old! A great piece of history and an absolute oasis.

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!

Charming Cottage on Private Maine Island

You'll feel the Magic of the Maine islands in cozy Oar Island Cottage. One of only two houses on a private island, it's the perfect balance between wilderness and comfort. A five-minute boat-ride brings you to a world of bird-calls, private swimming, and the scented pine forest. Have some high-quality family time by choosing something from our bookshelves, puzzles, or board games, or go see what fish are biting. Come see why so many guests love Oar Island!

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.

Private Lakeside Camping in Penobscot, Maine

Private lakeside camping on Toddy pond in Penobscot, Maine 50 min. from Acadia and Bar Harbor. This 400 foot private wooded lakeside lot is available for camping. This rental is close to Acadia, Ellsworth, Bucksport and the Blue Hill Peninsula. Go out and explore the area attractions or stay put and swim, fish, and kayak on one of Downeast Maine's most popular lakes; Toddy Pond.