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Waterfront holiday rentals in Islesboro

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Top-rated waterfront rentals in Islesboro

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

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Flat

4.85 out of 5 average rating, 102 reviews

Cottrill House on Damariscotta River #2

A convenient and newly renovated apartment. Enjoy the mid-coast in down town Damariscotta Maine. Private entrance, two bedrooms, private bathroom, living room, kitchen and dinning room. Private back yard with views over the Damariscotta River. Walk to unique restaurants and shops. Rent a kayak or a paddle board across the street and enjoy the beautiful views of the Damariscotta River. Only, 25 minutes away from Pemaquid Point and Beach. 32 miles to Popham Beach and Reid State Park. No smoking!

Guest favourite

Guest suite

4.97 out of 5 average rating, 107 reviews

Lake front luxury retreat with an Island View

Indulge in lakeside luxury at our modern, waterfront studio retreat! Perched on the water's edge, this pet-friendly haven offers: Private dock and lake access · Spa-inspired indoor and outdoor showers · Cozy fire pit for a relaxing movie night under the stars · Unbeatable views and direct access to the lake for swimming & soaking up the sun · The serene sounds of loons and unforgettable memories to cherish. A short drive from town, experience the best of Maine living in style and tranquility.

Guest favourite

Home

5 out of 5 average rating, 8 reviews

Hall Bay Haven

This brand-new waterfront cottage has it all! Killer views of the water from the large deck, screen porch, or through the wall of windows in the vaulted living area. Well-equipped gourmet kitchen, tiled bathrooms, outdoor shower, ramp and float, canoe and kayak, and much more. Convenient to Bath, Five Islands, Reid State Park. Walking distance to Robinhood/Derecktor Marina, Osprey Restaurant, and Robinhood Free Meeting House. Two queen beds and a very comfortable queen sleeper in LR.

Guest favourite

Home

4.92 out of 5 average rating, 100 reviews

Waterfront| Hot Tub| Fire Pit|King Bed|Near Acadia

Come unwind in our spacious home just feet from the waters edge! -Relax in our 6 person hot tub -Explore the lake with provided canoe and kayaks -Less than an hour to Acadia National Park -Outside fire pit and indoor fireplace -Enjoy Barbecuing on our grill overlooking the water -Unwind with a good novel in our lounger on the deck -High Speed Starlink wifi -Private master suite with jacuzzi tub -Family friendly with provided stroller, pack-n-play, and high chair -9' foot Shuffle Board!

Guest favourite

Farm stay

4.83 out of 5 average rating, 124 reviews

Westport Island 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.

Guest favourite

Flat

4.91 out of 5 average rating, 149 reviews

On the water. Walk to Southwest Harbor

If you want to be near the action of an active and interesting harbor, this is the place for you. You will have a front row seat to spectacular morning sunrises over the harbor, the comings and goings of the fishermen and the many boats docked at the marina and anchored in the harbor. This spacious four bedroom two and a half bath home is located at the Great Harbor Marina just half a mile from downtown Southwest Harbor. Walk to restaurants, art galleries, specialty shops and more.

Guest favourite

Home

4.99 out of 5 average rating, 142 reviews

Water's Edge-Oceanfront with Stellar View

Water’s Edge offers panoramic coastal water views in a 2-Bedroom+Loft, 1-Bath vacation cottage located feet from the shore. Ideally located between Acadia National Park’s Schoodic Peninsula and Mt Desert Island, your serene cottage has private access to the coast with wonderful views of Frechman Bay and Cadillac Mountain. Explore all the beauty of Acadia National Park, climb local mountains, kayak the Mt Desert Narrows or just watch the tides and mountains from your private deck!

Guest favourite

Guest house

4.89 out of 5 average rating, 104 reviews

Large adorable 1 bedroom loft with ocean frontage

What you will love - Modern living space - Ocean Access - Frontage on Union River - Close to everything - but seems like you are in the woods. - Abundant wildlife - Store within walking distance - Outdoor deck on river - Views of Ellsworth Harbor - Full kitchen and laundry - Full bath and Half bath for guests - Air conditioning - Upscale Contemporary Decor - Situated on a 10 acre lot, with large lawn, pond, and within a 2 minute drive to downtown Ellsworth Maine.

Guest favourite

Flat

5 out of 5 average rating, 163 reviews

Duck Cove Apartment

Enjoy salty sea air when you stay at this vacation rental apartment in Bernard, Maine! Bring along your own kayaks to take advantage of the waterfront property. Just a few miles from Acadia National Park and a 20-minute drive to Bar Harbor , the space allows you and your favorite travel companions to explore the beautiful surroundings with ease! It doesn't get any better than beautiful ocean views, direct water access, and the best lobster in the country;

Guest favourite

Flat

5 out of 5 average rating, 108 reviews

Sail Loft - Upscale Oceanfront on a Pier near BBH!

Welcome to Sail Loft, a one-of-a-kind vacation destination in Boothbay Harbor! You can't get any closer to the water than this! Imagine relaxing in style and comfort, right over the ocean, and having views from every window. It's like being on a boat but better! Our newly updated, spotless loft has all the amenities you could want, and is only a short walk to downtown. You will find a great mattress, with cozy bedding and fluffy towels.

Guest favourite

Home

4.81 out of 5 average rating, 237 reviews

Lobstermans Way

Overlooking Fort Popham, the Kennebec River and entrance to Popham Beach State Park. The eagle population is back and there is a nest on the Bay. Private dock for relaxing or fishing! NO HIDDEN FEES As others have additional hidden fees above and beyond the nightly rate- for sheets -cleaning etc.this is the total nightly fee

Guest favourite

Flat

5 out of 5 average rating, 31 reviews

Luxury Condo on Water's Edge in Boothbay Harbor

Luxury condo with charm and character of a cottage. Private deck on water’s edge; dock/float shared with other 2 units. 3 bedrooms, 2 full bathrooms, modern kitchen. Sleeps up to 6. It's my home part of the year when not rented, so I've included just about everything you could imagine to make your (and my) stay comfortable.

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for waterfront rentals in Islesboro

Free parking on premises

Air conditioning

Waterfront apartment rentals

Guest favourite

Flat

4.86 out of 5 average rating, 132 reviews

Large Home with Great View next to horse farm

Guest favourite

Flat

4.92 out of 5 average rating, 154 reviews

Stunning Royal Richmond 2 Br Apartment Get Away!

Guest favourite

Flat

4.93 out of 5 average rating, 130 reviews

Union River Retreat Private Apartment

Guest favourite

Flat

4.99 out of 5 average rating, 288 reviews

The Reach Retreat

Guest favourite

Flat

4.94 out of 5 average rating, 103 reviews

The American Eagle - Inn on the Harbor

Guest favourite

Flat

4.91 out of 5 average rating, 233 reviews

Private Apartment at Cabin Cove

Guest favourite

Flat

5 out of 5 average rating, 144 reviews

Welcome to "West Winds at Pemaquid"

Flat

4.82 out of 5 average rating, 310 reviews

Lakefront Vacation Apartment in Searsport ME

Waterfront house rentals

Guest favourite

Home

4.92 out of 5 average rating, 13 reviews

Harbormaster’s House: Picturesque Waterfront

Home

4.55 out of 5 average rating, 56 reviews

Heron Watch - Oceanfront Home on Private Cove

Guest favourite

Home

4.98 out of 5 average rating, 41 reviews

2 Acre Waterfront w/Canoes & Kayaks, Game Room

Guest favourite

Home

5 out of 5 average rating, 29 reviews

Waterfront Big House views of Acadia & dock

Guest favourite

Home

5 out of 5 average rating, 106 reviews

Waterfront Home on Tidal Falls

Guest favourite

Home

4.89 out of 5 average rating, 61 reviews

Stunning Location, ocean front & idyllic cove

Home

4.78 out of 5 average rating, 49 reviews

Sunset River House

Guest favourite

Home

4.92 out of 5 average rating, 115 reviews

Winter River Respite with Hiking Trails

Waterfront apartment rentals

Apartment

4.91 out of 5 average rating, 91 reviews

Marina side Stern condo

Apartment

4.75 out of 5 average rating, 8 reviews

Oceanfront, dog-friendly 2BR with harbor view

Apartment

5 out of 5 average rating, 8 reviews

Oceanfront Multi-level Condo with Prime Amenities

Guest favourite

Apartment

4.98 out of 5 average rating, 65 reviews

Toddy Haven: A Lakeside Condo Near Acadia.

Apartment

4.53 out of 5 average rating, 43 reviews

1BR Waterview | Deck | Partial AC

Apartment

4.83 out of 5 average rating, 112 reviews

2BR Condo w/ Ocean Views in Downtown SW [Seaglass]

Apartment

5 out of 5 average rating, 11 reviews

Best views on MDI 2 bdrm 2 bth condo waterfront

Quick stats about waterfront rentals in Islesboro

Total rentals
40 properties
Nightly prices starting at
£103 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore