Holiday houses in Islesboro

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Popular amenities for Islesboro holiday rentals

Other great holiday rentals in Islesboro

Top Guest favourite
Cabin in Sedgwick
4.98 out of 5 average rating, 84 reviews

The Cabins at Currier Landing Cabin 3: Pine

AlleRating, 5 stars2 weeks ago
Can’t say enough amazing things about our stay! The cabin and property are so thoughtfully designed and laid out, it’s so peaceful and relaxing. David & Bill shared local recommendations prior to our trip and all of them were 10/10 - from restaurants to general stores, everywhere we went was a standout. We knew going into it we’d be about an hour from Acadia, so the drive didn’t bother us. We spent our days in Bar Harbor and our evenings near the house, eating at incredible local spots exploring the Sedgwick area. The local snacks upon arrival were really the cherry on top.
Top Guest favourite
Treehouse in Brooks
5 out of 5 average rating, 17 reviews

Lakeview Tree-house

BelmiraRating, 5 stars3 weeks ago
Beautiful tree house for a weekend get away. One of the main highlights was kayaking on the lake it was serene and absolutely stunning. Toni provided everything we needed and was very responsive the whole time we were there. If you’re looking for a peaceful retreat to unplug and recharge, this treehouse is a hidden gem. I can’t wait to come back!
Top Guest favourite
Guesthouse in Searsport
5 out of 5 average rating, 81 reviews

Private oceanfront cottage- Steps to Penobscot Bay

Kim Rating, 5 stars1 week ago
One of my favorite Airbnb hands down!! It was just as pictures described, very peaceful, and extremely clean. My husband and I wanted to get away from the hustle & bustle but still have the attraction of vacationing close by. We loved this cottage!! I recommend 100%
Guest favourite
Apartment in Northport
4.95 out of 5 average rating, 22 reviews

Lone Star Lodge - Newly Renovated Studio

ElizabethRating, 5 stars1 week ago
The house was beautiful, pristine and spotless. The bed was very comfortable. Beautiful location, very quiet and peaceful. Looked just like the pictures. We were not disappointed.
Guest favourite
Home in Camden
5 out of 5 average rating, 32 reviews

Private Bright Forest House by Lake

EmilyRating, 5 stars9 months ago
This was my favorite Airbnb experience to date. Hannah and Aja's house was beautiful and welcoming. Their space and design is so thoughtful and we immediately felt right at home. Hannah was incredibly responsive and accommodating when our travel arrangements shifted last minute. Would certainly recommend this home if you are traveling with a toddler as their space is fully equipped for a young child. Our family had the best stay at this home and are eager to return ASAP.
Guest favourite
Home in Northport
4.98 out of 5 average rating, 42 reviews

Cliff House - Ocean Views! Architectural designed.

Jeff & StephRating, 5 stars5 months ago
By far the best home away from home that any of us have ever stayed at. Better than the photos. Cleanest Airbnb I’ve ever stayed at. Can’t say enough. I am so glad we booked Mark’s place for our Christmas vacation, it was definitely one to be remembered.
Guest favourite
Home in Hancock
4.97 out of 5 average rating, 38 reviews

Private Oceanfront Home: Hot tub, Games, Fire pit

AmyRating, 5 stars2 weeks ago
This house was amazing—hosts really have thought of everything when it comes to guest experience! Kayaking out to the tiny islands in the bay a couple times allowed us to see horseshoe crabs and bald eagles up close. The fire pit was great and the “s’mores station” with supplies in the kitchen upon arrival was so cute and thoughtful. Our three kids loved this place and didn’t want to leave at the end of the week. Our boys especially loved the lower level game room with ping-pong, arcade games, and pop-a-shot. The kids also loved reading on the sofa in the upstairs loft overlooking the kitchen. The kitchen is well stocked and we cooked dinner there a couple times during the week. The hosts gave great local recommendations as well—the craft beer at Fogtown Brewing in Ellsworth (less than 15-min. drive) is excellent, and it is very kid-friendly with a large outdoor eating area and wood-fired pizza. We’d love to return to this house! Mosquitoes are fierce so bring bug repellent.
Top Guest favourite
Cottage in Hope
5 out of 5 average rating, 23 reviews

Lakefront Cottage at Salisbury Camp

TerriRating, 5 stars8 months ago
I loved my stay and Salisbury Camp. I was there in October during peak foliage and the view from every window was just stunning! The interior is beautiful, everything is high-end and well-done. Huge kitchen that had everything I needed. The yard is right on the shore, there’s a solo stove, kayaks and a canoe, and it’s just a peaceful spot to relax. Jenny was very helpful and proactive in all communications, and even provided welcome treats from Stonewall Kitchen, along with a bottle of wine. I had to leave a day early due to a family medical emergency and she was so thoughtful and kind. My only regret is that I didn’t get to use one of the kayaks to explore the pond. Next time! I definitely plan to return, this is such a wonderful spot!

Quick stats about holiday rentals in Islesboro

  • Total rentals

    200 properties

  • Nightly prices starting at

    $84 NZD before taxes and fees

  • Total number of reviews

    6K reviews

  • Family-friendly rentals

    140 properties are a good fit for families

  • Pet-friendly rentals

    90 properties allow pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

Destinations to explore

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