
Waterfront holiday rentals in Islesboro
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Top-rated waterfront rentals in Islesboro
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Popular amenities for waterfront rentals in Islesboro
Waterfront apartment rentals

Stunning Royal Richmond 2 Br Apartment Get Away!
The apartment is beautifully designed, spacious, relaxing, and comfortable. What more could you ask for? We enjoyed our 3-night stay. Read some of the assembled books on birds and enjoyed delicious food at the local restaurants. Alice was a gracious and responsive host. You will truly love staying in her apartment!

Union River Retreat Private Apartment
Quiet and convenient to Bar Harbor! Comfortable living area with a full kitchen. The hosts were proactive with details for a smooth stay.

Downtown waterfront Belfast with amazing views.
Absolutely beautiful place to stay! Would love to come back :)

Duck Cove Apartment
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!

Sail Loft - Upscale Oceanfront on a Pier near BBH!
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.

The American Eagle - Inn on the Harbor
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!

Waterfront Condo at the Sheepscot
This place is very convenient to everything! Well worth the stop for many nights!

Private Apartment at Cabin Cove
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

Unique Octagonal House with Private Beach!
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!

Water's Edge-Oceanfront with Stellar View
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.

Waterfront Farmhouse with Modern Flair!
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!

Sunny Waterfront Home Overlooking Blueberry Field
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).

Blue Arches: waterfront vacation home on 18+ acres
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!

Perched atop the Coast of the Atlantic Ocean
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!

Lavender by the Sea
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!

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

Harbor Heights
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!

Marina side Stern condo
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.

Oceanfront, dog-friendly 2BR with harbor view
Very nice place, totally renovated, spacious, cozy, and comfortable. It is located in a very beautiful area. We will be back for sure!

Toddy Haven: A Lakeside Condo Near Acadia.
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!

1BR Waterview | Deck | Partial AC
nice place

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

Best views on MDI 2 bdrm 2 bth condo waterfront
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.

3-BR Elegant Oceanfront Condo w/ Stunning Views
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
₹6,005 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
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- Acadia National Park
- Pemaquid Beach
- Samoset Resort
- Pemaquid Point Lighthouse
- Northeast Harbour Golf Club
- Coastal Maine Botanical Gardens
- Hermon Mountain Ski Area
- Dragonfly Farm & Winery
- Spragues Beach
- Eaton Mountain Ski Resort
- Pinnacle Park
- Sand Beach
- Kebo Valley Golf Club
- Pebbly Beach
- Rockland Breakwater Light
- Narrow Place Beach
- Bear Island Beach
- Three Island Beach
- Pebble Beach
- Indian Camp Beach
- Lighthouse Beach
- Hero Beach
- Farnsworth Art Museum
- The Camden Snow Bowl