Monthly Rentals in Islesboro

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Guest favourite
Guest house in Islesboro
4.97 out of 5 average rating, 36 reviews

Main Cabin at Coveside on Islesboro

KathleenRating, 5 stars9 months ago
This is the perfect Maine cottage experience. Easy to enter cove water for a swim. Cannot beat the view/sunsets. Sitting on front porch is the best. Very well stocked kitchen. Would stay again! Be aware there is no WiFi connectivity if you need that and one of us needed that for a work emergency so found public access. Us old folks found the lock box remote entry confusing. There was a small boat house close by and although visually blocked by trees could hear people talking on porch one night. Very little toilet paper supplied which based on how well everything else was likely an oversight but forced a quick trip to the Island market before it closed.
Top guest favourite
Guest house in Islesboro
4.96 out of 5 average rating, 26 reviews

Milk House

JacquelineRating, 5 stars4 weeks ago
The house is cozy and comfortable. Very easy to find. The host is great, very clear instructions.
Guest favourite
Cottage in Islesboro
5 out of 5 average rating, 101 reviews

Islesboro Boathouse

GiannaRating, 5 stars1 week ago
I had an amazing stay at the Islesboro Boathouse! The location was incredibly quiet and peaceful — a perfect getaway if you're looking to relax and recharge. The setting was beautiful, and I truly felt removed from the hustle and bustle. Mark was an incredible host — so kind and helpful, especially with navigating the ferry and anything else I needed. I couldn’t have asked for a better experience. Highly recommend!
Guest favourite
Home in Islesboro
5 out of 5 average rating, 17 reviews

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

HollyRating, 5 stars5 months ago
This house is very well designed and appointed for family gatherings. The kitchen is fabulous and allows a group to prep together and also be together. Having a butler's pantry and formal dining room made it even better. Having two other living spaces on the first floor was also nice to have time together and apart as we were a family of 6. Bedrooms are nicely appointed and the primary bedroom suite is huge and even has a sitting area. Location is perfect--right across from Dark Harbor and in a very walkable area.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term holiday rentals and a single monthly payment without additional charges.*

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Work-friendly spaces for digital nomads

Travelling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

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Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.

Destinations to explore

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