Waterfront vacation rentals in Islesboro

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Islesboro

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 348 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Guest favorite

Cottage in Wiscasset

4.87 out of 5 average rating, 215 reviews

Waterscape Cottage - private waterfront

A picturesque cottage perched on the hillside and visible as you cross the Davey Bridge. Elevated panoramic views of the Sheepscot R. and Wiscasset Harbor. When the Prince of Thailand owned the property the cottage was staff quarters! A rustic, comfy, quiet and peaceful little 2-story on 34 acres of woodlands. IN the woods so you may encounter creatures out and about - porcupine, ticks, mosquitoes, ants, fox, birds of prey and our hens, bees or dogs : ) 2 quiet furry friends welcome.

Guest favorite

Cottage in Owls Head

4.99 out of 5 average rating, 139 reviews

Coastal Maine contemporary cottage

Our cottage is meant to be both contemporary and rustic. It is where we go to get away from the hustle and bustle of the modern world and slow down. There is no TV or internet, even our phone is an old rotary one. You will see that we have a good radio, and games and books to read, and plenty of things to do outside. We hope you will take the time at our cottage to comfortably reconnect with yourself, and each other, while enjoying what Maine is renowned for, our quality of life

Guest favorite

Cottage in Deer Isle

4.91 out of 5 average rating, 120 reviews

The Sailors Retreat - Waterfront Home with Kayaks!

Retreat to this coastal Maine getaway just steps away from your own private ocean and beach front while roasting marshmallows by the bonfire enjoying the amazing view and a short drive to Acadia National Park. Spend the day exploring tidal pools, relaxing in the sun, kayaking, enjoying some Maine Lobster or take it easy and just enjoy a cup of coffee while taking in the spectacular views and listening to seagulls and waves crashing; Something to do for all members of the family.

Guest favorite

Guesthouse in Sedgwick

4.96 out of 5 average rating, 235 reviews

Tiny house with AC!!

A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

Guest favorite

Cottage in Deer Isle

4.94 out of 5 average rating, 292 reviews

Beachfront Guest Cottage - Year-round Hot Tub!

Our cozy guest cottage has easy beachfront/kayak/canoe access, and is located very close (within walking distance at low tide) to the public boat launch for larger boats. Great location to explore Deer Isle, Acadia (approx 1hr), Castine (45m), and the Bangor (1hr) area. Brave children and adults even swim from the beach but comfortable swimming ponds/lakes are 10m in several directions. The hot-tub is open year-round! Additional guests can be considered prior to booking.

Guest favorite

Cottage in South Thomaston

4.93 out of 5 average rating, 118 reviews

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.

Guest favorite

Guesthouse in Penobscot

4.99 out of 5 average rating, 169 reviews

Sea Pearl

Take it easy at this unique and tranquil getaway. Newly renovated, this is a perfect spot for your serious fun. Located right on water of the Northern Bay in Penobscot. The Northern Bay is considered the hidden Gem of the bay. This area of the bay is tidal. Come watch the eagles soar over head Just out your door. Kayaking, sailing, hiking, seafood , and lot more! Or just relax in a stunning natural setting. Just a short drive to Acadia National Park, & Bar Harbor.

Guest favorite

Tiny home in Blue Hill

4.84 out of 5 average rating, 133 reviews

Mini Moose Tiny Home

Our Mini Moose sits on our 65 + acres of beautiful Maine woods. Two miles from the center of the coastal village of Blue Hill. Five years of rentals. Fire pit & view of the pond from the deck. 2 paths around 2 ponds, swimming is allowed and a contemplative walking labyrinth. Perfect getaway for a couple or single person to explore the natural beauty of Downeast Maine. Only 45 minute drive to Acadia National Park and close to all that Downeast Maine has to offer.

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Guest favorite

Tiny home in Trenton

5.0 out of 5 average rating, 140 reviews

The Tiny House with the Enormous View of Acadia

The Tiny House on Goose Cove is the perfect place from which to enjoy your visit to Acadia National Park. Set on three acres of shore front property, the house features spectacular views of Mount Desert Island. The entrance to the Park, and the shops and restaurants of Bar Harbor, are just 20-25 minutes away by car. And when you've had enough of the bustle and crowds, you can retreat to the peace and serenity of this beautiful property.

Guest favorite

Cottage in Belfast

4.9 out of 5 average rating, 112 reviews

Belfast Ocean Front Cottage

This quaint ocean front cottage is surrounded by lovely flower gardens and a panoramic view of Belfast Harbor. You're 20 feet from the beach ,and a 10 min walk to town.We have recreational kayaks you can use to paddle about the bay and up the river. With a shabby-chic decor, lots of windows & light, the cottage will steal your heart & give you a Maine experience to remember!