House holiday rentals in Islesboro

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Popular amenities for Islesboro house rentals

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, 74 reviews

Luxe Liberty: Getaway with Heated Indoor Pool!

RitaRating, 5 stars1 week ago
What a wonderful experience! Rebecca was an absolutely outstanding host, always quick to respond and went above and beyond to ensure we had everything we needed. My family and I had such a peaceful stay. The home and location were incredibly tranquil, perfect for a relaxing getaway. The house and property were absolutely beautiful, and we loved sipping our morning coffee on the amazing balconies with the breathtaking views. There is so much space, and every room in the house is well thought out, functional, and cozy. The pool is even better than we hoped, so big and clean and in immaculate condition. We spent most of our time swimming and relaxing by the pool. We also enjoyed playing pool and having so many rooms to gather in with the comfort of plenty of new comfy furniture. Highly recommend for anyone looking to unwind for a vacation away from all the noise and chaos of daily life. Every single area was as described in the listing and better. Thank you for an unforgettable stay!
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 Brooklin
5 out of 5 average rating, 41 reviews

ZephFir House - Brooklin, Maine!

LizRating, 5 stars6 days 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.
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
Top Guest favourite
Home in Lincolnville
5 out of 5 average rating, 24 reviews

Cozy Country Cottage On 10 Acres

SuziRating, 5 stars3 weeks ago
The cottage was beautiful, I loved the artwork and light fixtures. The small details made Babettes home lovely and peaceful. I enjoyed watching the deer in the back meadow in the evenings and was most appreciative that my pup was welcomed there as well. I highly recommend if you tee looking for a quite get away
Guest favourite
Home in Belfast
4.91 out of 5 average rating, 77 reviews

Harbor View Loft in Downtown Belfast!

Katie BowlerRating, 5 stars1 week 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!
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!
Guest favourite
Home in Belmont
4.89 out of 5 average rating, 57 reviews

Harmonic Pond Retreat - Cozy and Relaxing Setting

KateRating, 5 stars3 months ago
Exactly what we wanted. Thanks!
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!
Guest favourite
Home in Belfast
4.93 out of 5 average rating, 15 reviews

The Eleanor - Maine Charm and Comfort on the Coast

GerberRating, 5 stars7 months ago
I loved the place I felt right at home, beautiful and cozy. beautiful view from the balcony, and from the bathroom upstairs.

Private house rentals

Guest favourite
Home in Northport
4.9 out of 5 average rating, 20 reviews

Dog-friendly Boatyard Cottage

AmandaRating, 5 stars8 months ago
We very much enjoyed our stay here. The hosts couldn’t have been any nicer. We loved the space was perfect for our needs. It was close to all that we needed but nice and quiet. The extra touches in the house like fresh flowers were lovely. Highly recommend this place.
Top Guest favourite
Home in Hope
4.98 out of 5 average rating, 59 reviews

Hobbs Pond Nature Retreat

TimRating, 5 stars1 day 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
Guest favourite
Home in Deer Isle
4.92 out of 5 average rating, 36 reviews

Lupine Landing

EmilyRating, 5 stars7 months ago
We couldn't have asked for a better experience! Noah's home is a little slice of paradise on the coast of Maine. It's private, cozy, and surrounded by stunning nature. We found the home very clean and well-cared for. My husband, children, and I spent a week unwinding at Noah's home and only wish we could have stayed longer. We particularly loved the fireplace, well-appointed kitchen, and the kayaks. Beds were super comfortable. Views were gorgeous and location perfect jumping off point to explore nearby Blue Hill and Deer Isle/Stonington. Highly recommend visiting during autumn. We can't wait to return!
Superhost
Home in Penobscot
4.86 out of 5 average rating, 42 reviews

The Loft

JillRating, 5 stars6 days 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 Searsport
4.98 out of 5 average rating, 50 reviews

Sun, Salt & Sand at Heart Rock House!

JessicaRating, 5 stars3 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!
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).
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.
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

    $116 NZD 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