Waterfront vacation rentals in Islesboro

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Popular amenities for Islesboro waterfront rentals

Waterfront apartment rentals

Guest favorite
A welcoming living area is showcased with soft furnishings in varied colors, including a green sofa and light blue armchair. A patterned area rug is placed under a coffee table. Natural light streams through a window adorned with sheer curtains, while a floor lamp and table lamp provide additional illumination.
Apartment in Richmond
4.92 out of 5 average rating, 156 reviews

Stunning Royal Richmond 2 Br Apartment Get Away!

Jen JenniferRating, 5 stars2 weeks ago
Very cute apartment, very clean. The only heads up for someone a little older or handicapped would be the stairs going up to the apartment were a little on the steep side.
Top guest favorite
A charming exterior view of the property showcases a well-maintained home surrounded by lush greenery. The landscaping features neatly trimmed bushes and trees, with a spacious driveway leading to the entrance. Sunlight illuminates the scene, enhancing the sense of tranquility.
Apartment in Ellsworth
4.93 out of 5 average rating, 131 reviews

Union River Retreat Private Apartment

AllisonRating, 5 stars2 weeks ago
Quiet and convenient to Bar Harbor! Comfortable living area with a full kitchen. The hosts were proactive with details for a smooth stay.
Guest favorite
A serene waterfront view features calm waters reflecting the sky, with boats docked along the shoreline. Trees in autumn hues frame the scene, while a pathway winds through the park, leading towards the water and inviting outdoor activities.
Apartment in Belfast
4.86 out of 5 average rating, 105 reviews

Downtown waterfront Belfast with amazing views.

MaddieRating, 5 stars7 months ago
Absolutely beautiful place to stay! Would love to come back :)
Top guest favorite
Large windows frame a scenic view of the waterfront, with the ocean visible in the distance. The window area is adorned with a colorful valance, adding a touch of charm. Natural light floods the room, creating a bright and airy atmosphere.
Apartment in Tremont
5 out of 5 average rating, 167 reviews

Duck Cove Apartment

JeremyRating, 5 stars6 days ago
We had a fantastic stay in Tremont! Nancy's place was spotless and well appointed, with a beautiful view of the water. The kitchen was well stocked with cookware and essentials (coffee, tea, sugar, salt etc), making it easy to cook several meals. The apartment is in a peaceful part of MDI, yet conveniently close to the island's sights and towns. Nancy was responsive and helpful - overall a great stay. Highly recommend!
Top guest favorite
A welcoming living space features two comfortable armchairs and a soft couch, with a wooden coffee table at the center. Large windows provide abundant natural light and views of the water. A well-equipped kitchen is visible in the background, along with light-colored cabinetry.
Apartment in Boothbay Harbor
5 out of 5 average rating, 113 reviews

Sail Loft - Upscale Oceanfront on a Pier near BBH!

JoyceRating, 5 stars1 week ago
The location is incredible! Ive never had such a great view. The place was clean and comfortable. Booth ay Harbor is very nice place to stay.
Guest favorite
A private deck is shown, featuring a small table and two chairs, overlooking a harbor scene. Boats can be seen in the distance against a backdrop of clouds and blue sky, creating a serene coastal atmosphere.
Apartment in Stonington
4.94 out of 5 average rating, 108 reviews

The American Eagle - Inn on the Harbor

LeslieRating, 5 stars1 month ago
So peaceful but off season. So not sure how it would be with lots of traffic and people. But the private deck and entrance was wonderful. The water view couldn’t have been more up close and personal with the beautiful harbor. The place was clean and cozy. Perfect lighting. Didn’t watch tv once. A convenient common room for extra supplies or a cup of coffee. Staff was very friendly when we were checking out. No front desk attendant and none needed. They answer messages quickly!
Guest favorite
Two white adirondack chairs are positioned on a grassy area overlooking a serene body of water. The landscape includes distant hills and a clear blue sky, complementing the peaceful waterfront setting.
Apartment in Edgecomb
4.85 out of 5 average rating, 483 reviews

Waterfront Condo at the Sheepscot

KathyRating, 5 stars1 day ago
This place is very convenient to everything! Well worth the stop for many nights!
Top guest favorite
A bright bedroom is filled with natural light from a large window, featuring a cozy bed covered with a patterned quilt. An octagonal window provides an additional source of light, while a bedside lamp offers soft illumination. A small green nightstand holds books and a decorative plant.
Apartment in Sedgwick
4.91 out of 5 average rating, 237 reviews

Private Apartment at Cabin Cove

JiaxinRating, 5 stars1 week ago
Nancy is a very friendly and kind host. The place is very quiet and tidy. It’s very easy for us to drive to Acadia National Park.

Waterfront house rentals

Guest favorite
An octagonal house is nestled among trees, with a green metal roof and wooden siding. A wide deck leads to the entrance, overlooking a calm body of water. Lush greenery surrounds the property, creating a serene natural setting.
Home in St. George
4.91 out of 5 average rating, 34 reviews

Unique Octagonal House with Private Beach!

SamRating, 5 stars1 month ago
Simply magical! Cozy and fun space. We enjoyed watching eagles and ospreys fish, seals pop their heads up, and even an adorable family of foxes from the comfort of the living room! Kitchen had all necessities for cooking most meals at home. A nice trail for walking down the road and an awesome beach where the kids threw stones and searched for seaglass each afternoon. We were all sad to leave!
Guest favorite
A coastal cottage is shown beside a rocky shoreline, surrounded by trees. The clear blue water reflects the sky, while the cottage features a large furnished deck that overlooks the serene landscape. The environment suggests a tranquil seaside retreat.
Home in Hancock
4.97 out of 5 average rating, 151 reviews

Water's Edge-Oceanfront with Stellar View

AmyRating, 5 stars3 weeks ago
Gorgeous ocean views right on the water! Every room has gorgeous photography on the walls, the house was extremely clean, everything clearly laid out in the house manual. Sunrises and moonrises over the ocean were stunning and unbelievable. Amazing location, super close to Tidal Falls. Drive to Acadia was easy and it is a great spot in between the Schoodic peninsula part of Acadia and the Bar Harbor part.
Top guest favorite
A spacious outdoor deck overlooks Winnegance Creek, with wooden railings and a small table set for two. The tranquil water and surrounding greenery provide a serene backdrop, while a select few yellow shrubs accentuate the scene, reflecting the natural beauty of the area.
Home in Bath
5 out of 5 average rating, 103 reviews

Waterfront Farmhouse with Modern Flair!

JosephRating, 5 stars2 weeks ago
We stayed for eight days and loved it! It surpassed our expectations and the open floor plan allowed our three generation family to spend great time just talking and spending quality time together. We were met with some great snacks when we arrived which came into handy after a long day of traveling from the west coast. We were captivated by the beautiful landscape including amazing eagles plunging into the waters and catching fish. The changing tides meant the landscape and natural activities were always providing a new show to enjoy. We loved everything about this stay and would highly recommend it!
Guest favorite
A bright and airy living space features large windows that overlook the peaceful waters of the Salt Pond. Comfortable seating arrangements include an armchair and chaise lounge, complemented by a decorative rug on polished wooden floors.
Home in Blue Hill
4.94 out of 5 average rating, 102 reviews

Sunny Waterfront Home Overlooking Blueberry Field

LisaRating, 5 stars3 weeks ago
This house is remarkably beautiful and welcoming. The walls of windows welcome sunshine throughout and the private views of the water are unmatched. Artistic details abound in the interior - like Anthro and West Elm had a baby. We vacationed with our toddler and my in-laws and we all had ample space to gather, as well as disperse. Highly recommend! Local recs: The Activity Shop for kayak rental delivery, pizza from Blaze, coffee from Bucklyn, brunch at Humblebee Cafe, sundries from Blue Hill Co-op, blueberry pie from Mount Desserts (on way to Acadia).
Guest favorite
A calm cove surrounded by dense green trees reflects serene water. A sailboat gently floats on the bay, complemented by soft rock formations emerging from the water's surface. Sunlight brightens the landscape, casting a tranquil atmosphere over the scene.
Home in Deer Isle-Stonington
4.95 out of 5 average rating, 154 reviews

Blue Arches: waterfront vacation home on 18+ acres

VictoriaRating, 5 stars2 weeks ago
The Hadley home was so beautiful and comfortable! We felt right at home in such a beautiful space. It was well stocked with kitchen items, which made cooking at the house a breeze. Mike was such a great and responsive hosts with great recommendations around town. Hope to stay again!
Top guest favorite
The rocky coast is lined with spruce trees, showcasing natural contours along the shoreline. Calm blue waters gently lap against the rocks, while a clear sky enhances the scenic view. A few homes are nestled among the trees, blending harmoniously with the coastal landscape.
Home in Georgetown
5 out of 5 average rating, 101 reviews

Perched atop the Coast of the Atlantic Ocean

BrianRating, 5 stars3 weeks ago
We had a wonderful stay! The house was impeccable with an incredible view of the ocean. We had everything we could want. Marsha was a wonderful host and we’re so glad we stayed here!
Top guest favorite
A charming cottage is framed by lush green trees and sits along the Penobscot River. The gravel path leads to the entrance, with water visible in the background under a clear blue sky, creating a serene setting for visitors.
Home in Orland
4.98 out of 5 average rating, 127 reviews

Lavender by the Sea

PrashantRating, 5 stars1 week ago
We had a truly unforgettable stay in Penobscot, Maine, and Suzanne’s Airbnb was a big reason why. The view from the property was absolutely stunning — serene, scenic, and the perfect escape from everyday life. Suzanne was an incredibly warm and gracious host who even invited us for breakfast and made us fresh coffee, making us feel instantly at home. Melissa, the property manager, was equally wonderful — welcoming, attentive, and always quick to respond to any questions we had. Both Suzanne and Melissa went above and beyond to make our stay comfortable and memorable. Their kindness made it feel like we were visiting family rather than staying in a rental. I’ll definitely be returning to Suzanne’s place for my next visit to Maine. Highly recommend this beautiful spot to anyone looking for a peaceful and heartwarming getaway!
Guest favorite
A spacious bedroom features large windows offering views of the lake and surrounding trees. Natural light fills the room, highlighting the hardwood floors. A wooden dresser and a small desk with a chair provide functional furnishings, while a cozy bed with a dark coverlet invites relaxation.
Home in Bucksport
4.96 out of 5 average rating, 153 reviews

Lake Front-Maine Themed-Soaking Tub-Fire Pit-Kayak

Lydia ARating, 5 stars2 weeks ago
The house was spacious, comfortable and came with everything we needed from cooking, to sleeping and even extra things for my pups! We celebrated my husband's 30th birthday and we arrived to a hand written card with food suggestions - very thoughtful. It was a great stay, and easy check-in/check-out!

Waterfront condo rentals

A serene view of Frenchman's Bay is captured in the image, featuring a boat gently gliding across the water. Lush greenery borders the scene, enhancing the tranquil atmosphere, while a clear blue sky stretches overhead.
Condo in Winter Harbor
4.5 out of 5 average rating, 38 reviews

Harbor Heights

KatonRating, 5 stars7 months ago
Great home in a great location. Very spacious and clean and Corey was very responsive. We had 0 problems with there being a restaurant down stairs. Beautiful views of the bay and a near by field where we watched little kittens playing with each other! It was adorable. We slept great and felt right at home!
Superhost
A rustic building with wooden siding and a wide balcony is shown. Hanging floral planters add color to the exterior while large windows allow ample natural light. The signage displays the name 'The Cannery,' indicating a dining establishment in an inviting marina setting.
Condo in Southwest Harbor
4.91 out of 5 average rating, 91 reviews

Marina side Stern condo

ShannonRating, 5 stars9 months ago
The photos don't do this place justice. It was spacious and squeaky clean. Beautiful views of the water. For a busy marina it was pretty quiet. During the day there would be people just outside the unit talking but nothing disruptive. Great price for a beautiful place. Only about a 25min drive to Bar Harbor. We would definitely stay here again.
A spacious living area features a light-colored wood floor, complemented by a blue area rug. Two blue armchairs and a large sectional sofa provide ample seating. A wall-mounted TV is visible, and sliding glass doors lead to a balcony with views of the harbor.
Condo in Boothbay Harbor
4.75 out of 5 average rating, 8 reviews

Oceanfront, dog-friendly 2BR with harbor view

MarconeRating, 5 stars15 months ago
Very nice place, totally renovated, spacious, cozy, and comfortable. It is located in a very beautiful area. We will be back for sure!
Top guest favorite
The exterior of the lakeside condo is illuminated at dusk, surrounded by tall evergreens. Warm light shines from the windows, offering a welcoming appearance. A gravel path leads to the entrance, bordered by a natural stone wall. The serene setting enhances the peaceful ambiance.
Condo in Orland
4.98 out of 5 average rating, 66 reviews

Toddy Haven: A Lakeside Condo Near Acadia.

EmilyRating, 5 stars7 months ago
We thoroughly enjoyed our stay and didn’t want to leave! Everything about the cabin was well thought out. We loved having a fire and looking at the stars from the dock! Mark and Laurie were fantastic, friendly hosts and made us feel right at home. We would love to come back someday!
An open-concept living area features a comfortable sofa and an armchair that provide seating for four. A dining table is positioned nearby. A flat-screen TV is mounted on the wall, and large doors lead out to a deck, offering natural light.
Condo in Edgecomb
4.55 out of 5 average rating, 44 reviews

1BR Waterview | Deck | Partial AC

OrandeRating, 5 stars11 months ago
nice place
Superhost
The open living area features a light-coloured sectional sofa positioned beside a coffee table. Large sliding glass doors provide access to the private deck, showcasing views of the harbor. A dining area and kitchen can be seen in the distance.
Condo in Southwest Harbor
4.84 out of 5 average rating, 117 reviews

2BR Condo + Ocean Views in Downtown SW [Seaglass]

TimothyRating, 5 stars1 week ago
Great location and clean. As noted in the description, the walls are thin, but we had no issues. The internet connection is spotty, in case you are planning to do some remote work, but we weren't, and had a great time.
Guest favorite
A tranquil view of Southwest Harbor at sunrise, featuring soft hues of orange and purple in the sky. Silhouettes of boats dot the water, while a tree stands prominently in the foreground. The scene captures the peaceful atmosphere of the harbor.
Condo in Southwest Harbor
5 out of 5 average rating, 12 reviews

Best views on MDI 2 bdrm 2 bth condo waterfront

ElizabethRating, 5 stars10 months ago
This condo was the perfect home away from home for our family vacation to MDI! Everything was excellent from the view to the location to the amenities to the helpful host. We would definitely stay here again.
A light-filled living space features a spacious teal sectional sofa and a patterned accent chair. A glass coffee table is placed at the center, complementing the soft area rug. Large windows allow natural light to illuminate the room, offering views of the harbor.
Condo in Boothbay Harbor

3-BR Elegant Oceanfront Condo w/ Stunning Views

MavisRating, 5 stars7 months ago
We can't say enough about the fantastic location and condition of Vacasa Maine's condo. It appeared the furnishings and everything is brand new. The decorating is very attractive and the unit was pristine in cleanliness. The best thing about it is the location. We could not have asked for anything better than to overlook the bay, watch the tide, the boat traffic, and the twinkling lights across the bay in the evening. The shops and restaurant's of Boothbay Harbor are within walking distance. We frequented the restaurant downstairs several times and were not disappointed. This was our first trip to Maine and your accommodations made it all we hoped for. We would definitely stay there again!

Quick stats about waterfront rentals in Islesboro

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$14,687 GYD before taxes and fees

  • Total number of reviews

    1.6K 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

  1. Airbnb
  2. United States
  3. Maine
  4. Waldo County
  5. Islesboro
  6. Waterfront rentals