House holiday rentals in Islesboro

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Popular amenities for house rentals in Islesboro

House rentals with a pool

Guest favourite
Home in Bangor
4.97 out of 5 average rating, 308 reviews

Cozy, fun, 3 bedroom home with a pool and Hot Tub.

源尘Rating, 5 stars3 weeks ago
Nice place! I had a great time here with my dog. The host gave us instructions when we arrived, and he response very quickly and friendly. Highly recommend
Guest favourite
Home in Waltham
4.92 out of 5 average rating, 24 reviews

Higgins Retreat Quiet Country Cape

RoyRating, 5 stars10 months ago
The house was perfect for us. Very clean and organized. Great host always responded in a timely manner. Was only about a 30 to 40 minute drive to Acadia National Park & Bar harbor, depending on traffic it could take longer. If we ever make it back to Maine I would definitely stay at the Higgins Retreat again. Thanks again Richard & Tina.
Guest favourite
Home in Bangor
5 out of 5 average rating, 28 reviews

New Boho Cape with Pool! Fenced yard, pet friendly

CindyRating, 5 stars1 month ago
Thank you Christina! Great weekend stay for UMaine graduation. Great location from campus and stores for the things we forgot (haha).
Guest favourite
Home in Liberty
4.91 out of 5 average rating, 75 reviews

Luxe Liberty: Getaway with Heated Indoor Pool!

WendyRating, 5 stars6 days ago
this was the 3rd time our family has stayed,again we had a fantastic time! We chose to return due to the great space, a fabulous indoor pool, great kitchen and an amazing view. Great attention to details, comfortable for large families or groups and peaceful for just 2.
Superhost
Home in Lincolnville
4.85 out of 5 average rating, 13 reviews

Coastal Retreat with Pool and Cheerful Vibes

AnneRating, 5 stars8 months ago
We felt like at home. The house is located in a private property with swimming pool and tennis courts. It’s very clean and very peaceful. Just a clarification about the description : there’s no bathroom in the basement. Then if you come with elderly people or very young kids, it could be annoying. If you like cooking, the kitchen is very well equipped. We´ll keep a very good memory of our stay in Ducktrap Retreat during the colorful foliage season.
Superhost
Home in Washington
4.86 out of 5 average rating, 7 reviews

House in the woods

SavannahRating, 5 stars6 months ago
Booked this place for our anniversary to get away from the city for a weekend.. we found exactly what we were looking for! The hot tub was wonderful, the house was clean and cute, and we had everything we could have needed! Estelle was very responsive and gave clear instructions for everything. Would recommend this place for a quiet getaway or a small group trip in the summer!
Superhost
Home in Stonington
4.95 out of 5 average rating, 20 reviews

The Boathouse at Spruce Harbor

Janette Is pronounced as YanetteRating, 5 stars9 months ago
My return visit to the Boathouse was even lovelier than I hoped it would be. The location can't be matched by anything else I've seen. I enjoyed a September visit with my dog and was lucky to have pristine weather. I lived a very simple and healthy outdoors life and came home the better for it. The Boathouse is true to its description: it is simple and rustic and uncomplicated but well-equipped, and is perfect for one-and-dog, or for two people. A little coming-and-going from the neighboring houses meant that I didn't feel isolated. Margaret is truly an exceptional and friendly host who communicates promptly and clearly. I almost hesitate to share "my" Boathouse location with too many of my back-home friends because it feels so intimate and special. I already want to be back there. I offer my deep thanks to Margaret and to the place that I could - briefly - call home.
Guest favourite
Home in Trenton
4.97 out of 5 average rating, 29 reviews

Acadia get away.! With pool and hot tub

JanelleRating, 5 stars8 months ago
I recently stayed with my family at this incredible Airbnb that exceeded all my expectations. This property offered a hot tub, a pool table, and a level of privacy and tranquility that made for a truly relaxing getaway. One of the highlights of our stay was being able to watch the northern lights from the hot tub – it was absolutely magical. We spent a week in Acadia, and the location was perfect, just 15-20 minutes from Bar Harbor or the nearest town. The hosts were very responsive, and the place was fantastic for families, being both kid and pet friendly. It was a week filled with unforgettable moments, and I can't recommend this place enough!

Weekly house rentals

Guest favourite
Home in Deer Isle
4.92 out of 5 average rating, 37 reviews

Lupine Landing

AlexandraRating, 5 stars1 day ago
We absolutely loved our stay at Lupine Landing. It was wonderful to be right on the water, especially with access to a beach and kayaks. The house was perfect for the two of us and our small dog, and had everything we needed: pantry staples, beach towels, sunscreen. The bathrooms seemed to have been recently updated which was also a great surprise. We would definitely recommend staying here and look forward to our next trip to LDI!
Superhost
Home in Penobscot
4.86 out of 5 average rating, 42 reviews

The Loft

JillRating, 5 stars1 week ago
What a dream it was to stay in this beautiful, dog-friendly spot! Being able to let my pups run, play, and explore the woods was such a gift. The loft, with its high ceilings, was warm and inviting, and the bed was so comfortable I didn’t want to get up! Tony was a kind and welcoming host—I’m already looking forward to my next stay.
Top guest favourite
Home in Belfast
5 out of 5 average rating, 26 reviews

Belfast Oceanside House - on downtown harbor walk

RobinRating, 5 stars5 days ago
There’s not enough words to say how wonderful Alana was from the initial booking to check out. We have booked a lot of Airbnb’s and this is our all time favorite. The location is amazing with the water view. I was so excited about the decor I spent an hour sending pictures to my daughter. We really loved the history behind the house too. This is our new go-to everytime we visit the area. Thank you for sharing such an incredible home!
Top guest favourite
Home in Searsport
4.98 out of 5 average rating, 50 reviews

Sun, Salt & Sand at Heart Rock House!

JessicaRating, 5 stars4 days ago
Five stars, all the way! Absolutely incredible house nestled on a private drive with the most gorgeous neighborhood beach. We really appreciated all the amenities and loving small touches that the owners put into their dream home. Would stay here a million times over again. Thank you so much for helping us create lifeline memories at the Heart Rock House!
Guest favourite
Home in Brooklin
5 out of 5 average rating, 41 reviews

ZephFir House - Brooklin, Maine!

LizRating, 5 stars1 week ago
We had an incredible stay at the Blue Hill Bay house! Nestled in a peaceful wooded setting, the home feels wonderfully secluded, yet inviting. The expansive windows, especially from the top floor loft, make you feel like you’re living in a treehouse. We loved spending evenings around the fire pit, which is surrounded by thoughtfully curated plants, creating a truly magical atmosphere. The grill was easy to use, making outdoor meals a breeze. Inside, the beds were comfortable and the bathrooms spotless. We also appreciated how thoughtfully designed the space was, especially since it's hard to find a cute place that also warmly welcomes dogs. If you’re considering a stay here, don’t hesitate, this place is a gem! We can’t wait to return.
Superhost
Home in Lincolnville
4.94 out of 5 average rating, 94 reviews

"The Roost" Cottage

SaraRating, 5 stars5 months ago
Highly recommend John's place. Perfect location - could walk to beach and get to other areas quickly. John was an excellent host. There to answer any questions, wasn't intrusive, and made a mean cup of coffee. Having the coffee shop next door was a HUGE perk! Place was spotless upon arrival and check in was seamless. I was pleasantly surprised that the place was larger than I expected. The primary suite had a a bonus seating area that I don't believe I saw in the photos as well as a small room on the first floor that had a daybed. We will surely be a repeat customer.
Guest favourite
Home in Belfast
4.91 out of 5 average rating, 77 reviews

Harbor View Loft in Downtown Belfast!

Katie BowlerRating, 5 stars2 weeks ago
We loved our stay in Belfast! Whitney is a great host. We enjoyed our welcome treat, the view from the balcony, and the comfortable, cozy feel of the house. We took a few great walks to the farmer's market, to town, and along the harbor walk and foot bridge. Thank you for the great guide book with local tips!
Guest favourite
Home in Camden
4.92 out of 5 average rating, 12 reviews

Camden Maine Renovated Cottage

AshleeRating, 5 stars9 months ago
We loved our time and stay at Elana’s place. The house is beautifully designed and decorated and we appreciated the thoughtful upgrades in bedding, soaps, overall decor, etc. We were a group of 4 (two couples) and we each had more than enough space to ourselves. We spent most of our time during the day out and about either on hikes (drove to Acadia one day!) or visiting the shops and restaurants in the village. Coming back to the house in the evenings felt like coming home. Camden is a postcard town with great food/ restaurants, nature activities and stunning views. We stayed for a full week and felt like we ran out of time. We can’t wait to come back!

Private house rentals

Top guest favourite
Home in Hope
4.98 out of 5 average rating, 59 reviews

Hobbs Pond Nature Retreat

TimRating, 5 stars2 days ago
Loved being at the cabin for the week. Coffee outside on the lower porch, walks down to the pond, and the cool breeze through the house in the evenings. The house had everything we needed and more. Definitely stop by Hope general store if you’re staying here! Hostess was available but not invasive, great experience
Top guest favourite
Home in Brooksville
5 out of 5 average rating, 35 reviews

Bob's Place

JackieRating, 5 stars8 months ago
My friend & I stayed 3 days. We planned to do some exploring & hiking & antiquing so it was right up our alley. The location is so quiet, peaceful & picturesque. It’s homey & tastefully decorated! And I loved the extra little touches, for example the bathroom toilet paper flower! So cute!! You can tell she takes pride in her home and in her guests comfort and that it is her passion! Also Bob’s place is bigger than it looks in the pictures. Susan is very thoughtful and easy to communicate with. She gave me some dining recommendations and also asked if we were able to see the northern lights. Who does that?! Susan does!! Thanks for an awesome stay!! Will be back for sure!!
Top guest favourite
Home in Stonington
5 out of 5 average rating, 14 reviews

Stonington Dream House

JacobRating, 5 stars2 weeks ago
Absolutely loved being in Stonington. Such a lovely town that felt true to Maine’s roots. Susan’s place is right at the heart of Stonington. The house has lots of rustic charm, we loved the views of the harbor. The kitchen was nice to have for breakfast and lunch, for dinner we were able to walk to restaurants right from the house. Worth noting that several restaurants are closed before the first weekend of June and/or on weekdays (Monday especially).
Guest favourite
Home in Camden
4.97 out of 5 average rating, 31 reviews

Newly Renovated Craftsmen Bungalow in Camden

OmarRating, 5 stars7 months ago
Really enjoyed staying at Ben and Lauran's place! It's close enough to town to walk, but also removed enough to have peace and quiet.
Guest favourite
Home in Friendship
4.93 out of 5 average rating, 54 reviews

Family Escape w/ Kayaks, Fire Pit, & Water Access

DeliaRating, 5 stars1 month ago
What a whimsical town! In the middle of nowhere So peaceful Yet, Wallace's General Store, right up the road Maybe a mile Amazing food and Sandwiches and just about everything under sun to Need So, just down the road is this Amazing Place! Three Sisters Farm Heaven Awaits Must check out
Guest favourite
Home in Brooklin
4.89 out of 5 average rating, 19 reviews

Comfortable, quiet home in Brooklin, Maine

LilaRating, 5 stars8 months ago
The house was cozy and comfortable with all amenities we could need. The kitchen was huge and had a ton of pots and pans and every implement and accessory we could possibly want. We loved the living room, which was filled with books and music, and an invitation from RIch to listen to/read whatever we liked. We also loved the quiet surroundings. It was lovely and peaceful. I would definitely recommend the property and the owner.
Superhost
Home in Northport
5 out of 5 average rating, 4 reviews

Lovely Cottage on Penobscot Bay

Mary PatRating, 5 stars9 months ago
We had a magical weekend at this quintessential Maine cottage, nestled among others and right on the water, complete with a porch perfect for studying the tides and the stars. The area is just lovely—walking down to Bayside to admire the Victorian cottages and take a swim or a quick drive to Belfast for meals and shopping. Suzanne’s suggestions made for a great weekend and we could have stayed much longer with lots to do (and more time on the porch). While the bedrooms are all close together on the second floor, the cottage lives larger than it looks, with a comfortable kitchen, two sitting rooms, a windowed dining room and of course that porch! We loved our time here and hope to come back!
Superhost
Home in Belfast
4.9 out of 5 average rating, 97 reviews

Entire House/Mill/modern vintage on 35 Acre Pond

MayaRating, 5 stars2 weeks ago
We had a very nice stay at Mill House! Patrick and Martha were quick to respond to my messages. We had a very rainy weekend and they gave great recommendations to help our stay in Belfast be memorable! The house was clean and comfortable and we loved birdwatching every morning with our coffee on the back deck. Simply beautiful! Thank you for a great stay!

Quick stats about house rentals in Islesboro

  • Total rentals

    60 properties

  • Nightly prices starting at

    ₹6,031 before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

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