Waterfront holiday rentals in Oakland

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Popular amenities for Oakland waterfront rentals

Waterfront apartment accommodation

Top Guest favourite
Apartment in Cornville
4.87 out of 5 average rating, 134 reviews

Large Home with Great View next to horse farm

WilfredoRating, 5 stars3 weeks ago
Beautiful and peaceful place! Just admiring the surroundings let the peace and tranquility set in and consume you. Highly recommend! Teresa is a wonderful host and flexible to your needs. Will definitely visit again, thank you Teresa!
Guest favourite
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 favourite
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.
Guest favourite
Apartment in Kingfield
4.96 out of 5 average rating, 363 reviews

On The River 2 with Lucy the resident cat

IsaahRating, 5 stars3 weeks ago
we always look forward to having a good stay here when its 1 day or a couple. Patricia is always friendly and always helpful for the area. Great host and great spot. highly recommend
Top Guest favourite
Apartment in Damariscotta
4.94 out of 5 average rating, 372 reviews

Cottrill House on Damariscotta River # 1

ChristopherRating, 5 stars4 days ago
Very comfortable. Terrific location. Lissette was very attentive, friendly and helpful. Would recommend her home to family and friends.
Guest favourite
Apartment in Edgecomb
4.86 out of 5 average rating, 487 reviews

Waterfront Condo at the Sheepscot

TeddiRating, 5 stars4 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 favourite
Apartment in Freeport
4.98 out of 5 average rating, 265 reviews

Beekeeper's Cottage- Peaceful,Quiet - Ocean Front

MarissaRating, 5 stars8 months ago
Our stay at The Bee Keepers Cottage was amazing. The property met our needs perfectly and it was super cute and cozy. The host was very responsive and communicative. And for any star gazers out there, the sky on a clear night is mesmerizing.
Top Guest favourite
Apartment in Caratunk
4.99 out of 5 average rating, 111 reviews

Caratunk Waterfront Studio

SarahRating, 5 stars8 months ago
This is a great spot, convenient to lots of outdoor activities in the area. The studio has super comfortable beds, a very well equipped kitchen, and even some nice touches like throw blankets, books, and games for days you want to stay in and get cozy.

Waterfront house rentals

Guest favourite
Home in Newport
4.94 out of 5 average rating, 126 reviews

Sugarmaple Lakehouse - Sebasticook Lake Newport ME

DanielleRating, 5 stars2 weeks ago
Great location. Woke up to the sounds of birds. very responsive. I would have given it a 5 star all the way, David was amazing and responded in a very timely manner. But, the turn over service could have been much better. The previous guest left a wine bottle in the automatic fridge ice dispenser and it was unfounded until my family found a large peice of glass in their drink, serious hazard to drink glass. Should have been spotted by the turn over service but, who would check the ice maker for a bottle a wine? I understand that. Very uncommon and unfortunate for us. David responded in a very fast manner and gave us options to accommodate the situation. I would have left a 5 star if this was the only thing but everything was so unorganized in the kitchen, they had everything but nothing made sense to why it was there. Sink didn't drain. There were also stains on the sheets and a pizza box left by the fridge that wasn't ours. Little things but the turn over service was a let down.
Guest favourite
Home in Belfast
4.96 out of 5 average rating, 138 reviews

Cove House

SusanRating, 5 stars8 months ago
We have been going to this area of Maine for over fifty years. I found this gem several years ago and haven’t stayed anywhere since. I find it to be peaceful, walkable to the center via footbridge, it’s all that we want. Kathy is a great host, quickly responds to any questions or needs you may have. We always know we will have a great experience staying here.
Guest favourite
Home in Naples
4.99 out of 5 average rating, 125 reviews

LUX Designer Private Waterfront

CodyRating, 5 stars3 weeks ago
We came here for a private getaway on our honeymoon and it did not disappoint. The price was a bit much, but for such a special time I felt it was worth it at the time I booked, and worth it it certainly was. beautiful, quiet, serene, it was perfect for a getaway. I would absolutely recommend, and I already have, this stay. 10/10
Superhost
Home in Pittsfield
4.82 out of 5 average rating, 124 reviews

Cozy Waterfront Home With Breathtaking Views!!!

JessicaRating, 5 stars1 week ago
We had an amazing time. TJ was very responsive and gave his secrets for fishing! He also accommodated a request that was an overlook on my part. I can’t say enough good things about the place itself or how nice TJ was. It was a phenomenal experience all around!
Superhost
Home in New Portland
4.85 out of 5 average rating, 143 reviews

The Riverfront Retreat - 27 minutes to Sugarloaf!

StephanieRating, 5 stars3 weeks ago
Great little cozy spot, clean, lots of plants and lights. Very comfortable. Nice little spot on the property by the stream. Close to a variety of hikes and waterfalls. Very happy with our stay.
Top Guest favourite
Home in Pittston
4.99 out of 5 average rating, 146 reviews

Riverside

MarleneRating, 5 stars3 weeks ago
This was my 5th time going there and I love it! The house is so cozy & very clean. The property is large and the view is breathtaking over looking the river. They are also pet friendly so we were able to take our Lhasa Apso Revy on vacation with us. Besides how great this Air BnB is, my favorite is the hosts Kent & Tish! They are wonderful people. They are kind & friendly, & have such beautiful souls. They have become family to me! I highly recommend getting this air bnb!! Thank you again Tish & Kent! Ian, Revy, & I are always happy to see you!!
Top Guest favourite
Home in Bath
5 out of 5 average rating, 104 reviews

Waterfront Farmhouse with Modern Flair!

BrendanRating, 5 stars3 weeks ago
We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!
Top Guest favourite
Home in Newcastle
4.99 out of 5 average rating, 159 reviews

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

RandyRating, 5 stars3 weeks ago
My wife and I completely enjoyed our stay at Ani’s place. She literally thought of everything any guest could ever want. Beautiful surroundings…walking distance to the Fish Ladder….a couple of miles to all the restaurants downtown. And the place itself is immaculate. The kitchen was perfect for eating in every night. This place is an absolute no-brainer to rent and we can’t wait to return!!!

Waterfront condo accommodation

Condo in Boothbay Harbor
4.75 out of 5 average rating, 8 reviews

Oceanfront, dog-friendly 2BR with harbor view

MarconeRating, 5 stars16 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!
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
Condo in Rangeley
4.9 out of 5 average rating, 40 reviews

2 Rangeley Lake unit 2 Condo Dock, Kayaks and more

DeborahRating, 5 stars3 months ago
This is the second time staying at Debi's Rangeley Lake Condo. It is a perfect location to stay if you're skiing at Saddleback or just exploring the area. Debi is very responsive to any questions. The condo is comfortable and the kitchen has everything you need to have dinner at "home". When we're in the area, we would definitely stay here again.
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!
Top Guest favourite
Condo in Belfast
5 out of 5 average rating, 17 reviews

Harbor View Cottage Unit A 2 bedroom downtown

BrandonRating, 5 stars9 months ago
What a beautiful location and house. There’s nothing better than sitting in the living room or front porch and being able to see the Belfast Bay. The house is very clean and neat. Beds are comfortable, shower is very hot. Don’t miss the sunrise in the mornings. Overall this is one of our favorite places we have stayed in Belfast.
Condo in Rockport

Samoset Resort Oceanfront Condominium

ArleneRating, 5 stars84 months ago
This place is absolutely amazing. It was larger than expected. It looked smaller in the pictures. Everything in the apartment was squeaky clean and we had every single thing we needed, from pots and pans to board games. Great ocean view from the porch, the living room and from one of the bedrooms. I loved seeing the boats pass by. So peaceful! I stayed there with my elderly mom, my teenage daughter and her friend for 4 days. There was so much to do! We enjoyed both the outdoor and the indoor pool. The kids took advantage of the Health Club by playing ping pong, badminton and going to the video game room. They also spent several hours playing chess in a very nice room near the lounge area that had a gorgeous ocean view. We had dinner at the Italian restaurant in the resort and were impressed by the amazing view. Great service. We also enjoyed the long walk to the lighthouse right next to the resort, and loved going to Camden, such a charming little town, 10 minutes away. The hostess, Laurie, was very accommodating, super nice, and communicated with me frequently, making sure I had all the answers I needed. I would definitely go back there! Glad to have made such wonderful memories! We didn't want to leave!
Condo in Standish
4.26 out of 5 average rating, 23 reviews

Cozy Lakeside Studio w/ Private Swimming Area

KyleRating, 5 stars8 months ago
Really loved this property! The unit provided a very cozy stay, and several amenities were provided. Very quite, peaceful stay and a great view of the lake from the porch! Would definitely plan to stay here again in the future!
Condo in South Thomaston
5 out of 5 average rating, 4 reviews

Ocean Front - Penobscot Bay - New 4 season home

SheriRating, 5 stars10 months ago
Simply perfect! Everything in the kitchen is new, in working order, extremely well-stocked. The home is clean and comfortable with amazing fine art everywhere. And the view! We couldn't get enough of the beauty, watching the Ospreys fishing, walking the little beach. Lots of hiking close-by. Rockland has great seafood market, bakery, bookstore. The Transportation Museum is excellent.

Quick stats about waterfront rentals in Oakland

  • Total rentals

    40 properties

  • Nightly prices starting at

    $166 NZD before taxes and fees

  • Total number of reviews

    890 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Oakland
  6. Waterfront rentals