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Waterfront vacation rentals in Orr's Island

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Orr's Island waterfront rentals

Waterfront apartment rentals

Guest favorite
Apartment in Portland
4.96 out of 5 average rating, 158 reviews

62 Views

SandraRating, 5 stars1 week ago
My husband, toddler and I stayed here and had a great time! We loved sitting on the roof deck and the living room has an amazing view of the water. We walked almost everywhere, which was so nice. Overall great location! Would recommend to anyone!
Guest favorite
Apartment in Richmond
4.92 out of 5 average rating, 158 reviews

Stunning Royal Richmond 2 Br Apartment Get Away!

MaryRating, 5 stars3 weeks ago
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!
Top guest favorite
Apartment in Boothbay Harbor
5 out of 5 average rating, 115 reviews

Sail Loft - Upscale Oceanfront on a Pier near BBH!

WestonRating, 5 stars4 days ago
In short, a unique experience where we met a few extremely friendly people. The property has amazing views of the harbor without noisy working boats. We would out this at the top of our rental experiences.
Top guest favorite
Apartment in Portland
4.96 out of 5 average rating, 115 reviews

Penthouse Two Master Waterfront Suite with Rooftop

TimRating, 5 stars2 weeks ago
These accommodations were perfect! Overlooking the Casco Bay harbor, the view was even better than depicted in the pictures. The condo was meticulously clean and very well appointed. The beds and pillows were so comfortable we slept even better than we do at home. The location could NOT have been better! It overlooks Portland’s old-town shopping district, and is easily walkable to all of the best restaurants in town. There is a beautiful walking trail just up the street, and you can easily catch the ferry to the islands from this location. It is convenient, beautiful and welcoming.
Guest favorite
Apartment in Edgecomb
4.86 out of 5 average rating, 487 reviews

Waterfront Condo at the Sheepscot

TeddiRating, 5 stars5 days ago
We had a lovely night at Audray’s place! The location & the views exceed expectations. It was clean, cozy and inviting. Edited to add- not reducing stars for this because we enjoyed the accommodations, but I want other travelers w/ pets to be aware: Audray reached out 24+ hours after we checked out to say her cleaning person reported “an excess of pet hair on furniture and linens than her washing machine could not handle”, and requested we mail her an extra $50 to cover special laundering. We sent $75 on platform instead as we were shocked and sorry to hear this. We found it surprising b/c were in the condo only 14 hours, we immediately covered the furniture w/ pet covers (we brought our own) upon arrival, we covered the beds w/ our own extra top sheets to protect the quilts from pet hair, & we do not let dogs sleep in the beds- we bring pet beds. We have only received compliments on cleanliness & exclusively 5 star reviews from hosts over 7 yrs and 23 stays all w/ multiple pets.
Top guest favorite
Apartment in Bristol
5 out of 5 average rating, 146 reviews

Welcome to "West Winds at Pemaquid"

ToddRating, 5 stars5 months ago
We had a great stay here. The apartment was perfectly clean and well appointed. Bob and Laura covered everything; thoughtful snacks, a comprehensive guest book, fully stocked kitchen and they even made umbrellas available. We were super comfortable and it was a great spot to base our Bristol adventures from!
Superhost
Apartment in Damariscotta
4.85 out of 5 average rating, 520 reviews

"Ship Shape": waterfront, cozy studio- downtown

AndrewRating, 5 stars1 day ago
Great location in town. Easy walk to Main St. and all that it offers. Space is as described and good for a short stay.
Top guest favorite
Apartment in Boothbay Harbor
4.95 out of 5 average rating, 375 reviews

Deckhouse with Footbridge Views!

PaulRating, 5 stars1 week ago
The Deckhouse was a wonderful and comfortable stay. Margaret immediately made us feel welcome as we checked in. She gave us a quick run down of the house and some fantastic recommendations. Easily walkable into the business district across the footbridge. A super short drive from the Coastal Maine Botanical Gardens and other great spots to explore. The deckhouse also makes for a great spot to sit and relax watching the waterfront at work. We would certainly come back.

Waterfront house rentals

Top guest favorite
Home in Freeport
5 out of 5 average rating, 47 reviews

Waterfront Cottage in Freeport

BrianRating, 5 stars3 weeks ago
Beautiful location on the water with stunning views, tranquil and peaceful with plenty of osprey and bald eagle sightings (there is a nest across the bay on Pettingill Island visible from the property). The house is very well-appointed and well-decorated. Irena was very communicative and responsive, and the house directions are clear and complete. We would stay there again. Thank you!
Top guest favorite
Home in Windham
4.94 out of 5 average rating, 141 reviews

Waterfront Gem walkable to Restaurants!

WindyRating, 5 stars5 days ago
a wonderful place to stay.
Superhost
Home in Harpswell
4.81 out of 5 average rating, 43 reviews

Orchid Harbor, Bailey Island 3BR

NikkiRating, 5 stars3 weeks ago
We really enjoyed the view of the water from the cottage. It had ample sleeping space for 8 people. We enjoyed the provided chairs by the water to relax in the evening.
Guest favorite
Home in Wells
4.87 out of 5 average rating, 119 reviews

Drakes Island Beach Front Breathtaking Property !

PhilippeRating, 5 stars4 weeks ago
We had a wonderful stay at this beautiful beachfront home with our extended family, including a total of 6 adults and 5 kids. We had two additional adults spend one night, there was plenty of room for everyone. The house was spacious, comfortable, and perfectly suited for a group of our size. The location is unbeatable, right on Drakes Island Beach, with incredible views and direct access to the sand. While we didn’t go in the water, we spent plenty of time relaxing on the beach, walking along the shore, and enjoying the peaceful setting. The home was clean, well-maintained, and stocked with everything we needed. The large deck and open living spaces gave us plenty of room to spend time together and unwind. This was a perfect spot for a relaxing family getaway, and we’d absolutely return again. Highly recommended!
Superhost
Home in West Bath
4.86 out of 5 average rating, 120 reviews

Oak Leaf

KayRating, 5 stars1 week ago
Enjoyed our stay very much! Lovely location on the water. Some white traffic noise but worth it watching the boats and wildlife! Comfy bed. We slept very well. Well-stocked kitchen. The location is perfect for lots of little day trips. Our only disappointment was the size of the smallest room. It’s very tiny. Great for a child but pretty tight for our adult son. Host was attentive. We will be back!
Guest favorite
Home in Boothbay Harbor
4.93 out of 5 average rating, 123 reviews

Renovated home with amazing waterfront views

NicoleRating, 5 stars1 month ago
Thoroughly enjoyed our stay! We unexpectedly had beautiful cloudless days most of the week. Great location & easy to get to the Harbor and Southport both of which we enjoyed! Recommend the Carriage House for a really top quality meal as well as Blue Moon Cafe (good lobster roll) which was one of Shirin’s recommendations. Would totally stay here again!!
Superhost
Home in Harpswell
4.92 out of 5 average rating, 24 reviews

Luxury Waterfront Tiny House

VirgginniaRating, 5 stars8 months ago
Love this little place! I would love to visit in the summer, and check out all the places that were closed for the season. It is 40 mins away from Portland for those hoping to visit there and stay here. But it is doable. The views were incredible, and it makes for a beautiful getaway.
Superhost
Home in Phippsburg
4.8 out of 5 average rating, 238 reviews

Lobstermans Way

SuzanneRating, 5 stars10 months ago
This was our family’s second stay at the Bay House. We love the ever-changing views from the picture windows and watching the various birds fly about. We enjoyed using the included beach pass to the state park, but were also comfortable staying in to play board games on the one rainy day we had. I’m sure we’ll be back to visit Popham Beach in the future!

Waterfront condo rentals

Top guest favorite
Condo in Portland
4.99 out of 5 average rating, 96 reviews

Charming, newly remodeled space atop Munjoy Hill.

ChrisRating, 5 stars7 months ago
Unit was very clean, situated in a quiet residential area and within walking distance to many of Portland's best bars, restaurants and attractions. Host was communicative and provided clear guidance on check-in/-out procedures and offered up suggestions to local attractions. On my recommended list - dinner at Twelve (one of the best restaurants in the US, IMHO); on-site food truck tacos washed down with a Hazy IPA at Bellflower or Austin Street Brewery; an everything bagel with lox & morning latte at Forage; the East Promenade for a food truck lunch, then a stroll along the waterfront trail to the port area for an ice cream cone at Gorgeous gelato; afternoon coffee at Double Great Coffee; and a post-dinner whiskey @ Independence Ice. Only downside on my visit was the upstairs neighbor. Dude clearly isn't a principal dancer in the Portland Ballet, as light on his feet wouldn't describe him. Not a stereo or TV issue - you can just hear the noise from him walking (8AM-10PM when there)
Guest favorite
Condo in Old Orchard Beach
4.91 out of 5 average rating, 432 reviews

Luxury Beach Front Condo! Prime Location!

KellyRating, 5 stars6 days ago
This place is gorgeous and right on the ocean!!
Guest favorite
Condo in Old Orchard Beach
4.91 out of 5 average rating, 68 reviews

Rustic Retreat studio, steps to the Beach. Unit #3

TylerRating, 5 stars3 days ago
The place was very easy to find, great location. Walking distance along the beach and sidewalk to attractions, great access to the beach. Very clean and well maintained place. The hosts are very responsive and polite with good recommendations of places to eat and things to do. Would definitely stay again!
Guest favorite
Condo in Old Orchard Beach
4.9 out of 5 average rating, 105 reviews

Oceanfront Condo with Awesome Views

NadiaRating, 5 stars1 month ago
I would recommend it 100%
Guest favorite
Condo in Lebanon
4.88 out of 5 average rating, 32 reviews

Quiet place on Milton 3 Ponds water front

JeremyRating, 5 stars3 days ago
Great place to stay. Beautiful scenery, very quiet exactly as advertised.
Guest favorite
Condo in Old Orchard Beach
4.85 out of 5 average rating, 93 reviews

The Brunswick

ChantelRating, 5 stars3 weeks ago
Great place to stay! Convenient location above the Brunswick with panoramic views of the beach and ocean, and a short walk to bars, restaurants, shops, and amusements. The condo is clean, spacious and well furnished. The living room and the balcony have plenty of room to relax and enjoy the views and sound of the waves. The king mattress is super comfortable. The keyless entry pads to both the building and condo make it easy to get in and out without having to worry about keys.
Guest favorite
Condo in Old Orchard Beach
4.73 out of 5 average rating, 119 reviews

Attractive 1 bedroom cabin only 50 ft from beach#1

SharonRating, 5 stars5 months ago
This cute little cottage was perfect for my stay in Old Orchard Beach. My stay was in cold January but the cottage was warm and cozy. The highlight was being steps from the beach and being able to roll out of bed and catch the sunrise each morning.
Guest favorite
Condo in Wells
4.98 out of 5 average rating, 42 reviews

NEW Beachside Wells Beach Condo with Pool

StevenRating, 5 stars2 weeks ago
Great small place right next to the beach. Amazing location no complaints. Definitely a popular spot in august I can only imagine!

Destinations to explore

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  3. Maine
  4. Cumberland County
  5. Harpswell
  6. Orr's Island
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