Photo by Colleen Johnson

Search Vacation Homes in Islesboro

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

31 Muh. - 2 Saf.

In two weeks

7 Saf. - 9 Saf.

In one month

21 Saf. - 23 Saf.

In two months

21 Rab. I - 23 Rab. I

Compare 361 Vacation Homes in Islesboro with updated reviews, rates, and availability.

"lovely little winer getaway. Cabin was everything we could have wanted. "

"Amazing cozy cottage with a breath taking view!"

located on Camden Harbor , we sit behind the Marina. Walk to everything !

"Very spacious and cozy. We had a lovely time, just a few housekeeping issues. Other than that, the host was very quick to reply. We arrived to fresh flowers , a bottle of wine, chocolate ,coffee and a welcome note… "

SAR 2,335 total

includes taxes & fees

17 Feb - 18 Feb

Small beach area located behind the house

"I was traveling with my 4 sisters. We enjoyed our stay very much. Hosts were very helpful with technical things and recommendations for places to eat and things to do. The cove on the ocean is great for sunrises and peaceful mornings. Beds were comfortable, Great place to wind down after a busy day!"

"Great little place with beautiful view and good location. Would recommend"

SAR 1,317 total

includes taxes & fees

26 Jan - 27 Jan

"Comfortable, convenient to family we were visiting."

SAR 1,108 total

includes taxes & fees

11 Feb - 12 Feb

Owls Head Vacation Rental | 3BR | 2BA | Stairs Required | 2,560 Sq Ft

"The house is lovely, great location and situation. The shore just below the house is rocky and charming, but requires caution descending to it (in the winter anyway). Sunrise over the south end of Monroe Island is just gorgeous. Views from every room. The kitchen is great, and the most generously supplied with cookware and dishes that I've ever seen in a rental. Super."

Estate on the sea. The house has been restored to its original "shingled" look.

"Such a wonderful spot to sit relax and catch up! "

SAR 8,002 total

includes taxes & fees

27 Jan - 28 Jan

"Our primary objective was a clean cost-effective one night stay for a road trip through New England. This was right on the road, which was convenient but a little bit noisy at night."

SAR 932 total

includes taxes & fees

27 Jan - 28 Jan

Looking out towards Maine coastline during fall, 5 minutes walk to quiet beach.

"Exactly what we were looking for. The house and the surrounding area is beautiful! We definitely will return back soon. Thanks! "

"My grandson was so excited to see the bobcat in the yard. We’re no strangers to wild animals what a great home you have. Thanks for sharing your home with us. We would like to come back "

"The house was very clean, comfortable and quiet. We had everything we needed for a great getaway. The location was perfect for everything we wanted to do - would highly recommend!"

SAR 1,141 total

includes taxes & fees

24 Jan - 25 Jan

"We stayed here for almost two weeks in late June/early July. The location was great for our purposes (we come to the area each summer to see family who live just minutes away), and we enjoyed walks with our preschooler down to the little beach to hunt for sea glass. We also liked the large yard and beautiful newer deck for added enjoyment outside - the view is lovely. The house is an older farmhouse with some updates; we expected and enjoyed the more vintage touches. The upstairs can get hot,...

Little island, mussel ridge channel, all the boats go by the house

"My wife and I enjoyed our stay in Owls Head. It was perfect for us. Hiking trails nearby and good seafood not far away"

"This place is very clean and the rooms are large. I enjoyed the walk down to the water, which is close by. Kitchen was well stocked. I, too, felt a railing on the stairs would be helpful. I am new to the Vacasa connection, so that took some learning, but all went well. "

"The house is new, absolutely immaculate and filled with light. The fully equipped kitchen was a joy to work in. The proximity to both Belfast and Camden was a huge plus. Our 2 dogs loved the open grassy field! A very friendly neighborhood too."

"This was a perfect, toasty warm, place for family to stay over the Christmas holiday. The open floor plan on the first floor is wonderful for communicating. The one year old enjoyed walking around this area. We enjoyed the big dinning table for meals, board games, and wrapping gifts. The beds were very comfortable. Two of the bedrooms have a water view in winter! The property managers are exceptionally attentive. They went above and beyond coming first thing in the morning to shovel snow!"

SAR 2,004 total

includes taxes & fees

30 Jan - 31 Jan

"Cozy, quiet cabin with a good layout and nice view on the water. Easy check-in and check-out process. Host is very responsive. "

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Islesboro

"Cozy, quiet cabin with a good layout and nice view on the water. Easy check-in and check-out process. Host is very responsive. "

"We just finished a five-night stay at this property. Rustic is the perfect way to describe it along with offering modern amenities like 1 and 1/2 baths, a complete kitchen, washer dryer and great internet. It's a great secluded location with the General Store just a five minute drive away."