Islesboro Island Rentals
From $274 per night (USD)VRBO
Comfort & quiet on an island off the Maine Coast.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Red House was a farmhouse for a working farm from the late 1800s until the mid-1900s. Miss Grace, the daughter of th ...
From $274 per night (USD)VRBO
From $165 per night (USD)Expedia
Island log home in Maine with ocean views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Modern 2 bedroom log home on Islesboro, an island off the coast of Maine with daily ferry access. Secluded lot. One qu ...
From $165 per night (USD)Expedia
From $136 per night (USD)VRBO
Inchcliffe--Islesboro Island Waterfront Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
If you are a small family of two or three looking for a quiet and beautiful place in which to spend a vacation, please ...
From $136 per night (USD)VRBO
From $372 per night (USD)VRBO
Historic Seaside Cottage with its own beaches overlooking Penobscot Bay..
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The Gables is a historic cottage built in the mid to late 1800's and has always been family owned. The 2 plus acre prop ...
From $372 per night (USD)VRBO
From $581 per night (USD)VRBO
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and c ...
From $581 per night (USD)VRBO
From $368 per night (USD)VRBO
\"The Dory\" on Penobscot Bay, Mid-Coast Maine
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Looking over Penobscot Bay, "The Dory" is a perfect place to relax and enjoy island life. Set on a dead end street in a ...
From $368 per night (USD)VRBO
From $237 per night (USD)VRBO
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This summer cottage on an island in Maine overlooks the beautiful Penobscot Bay. This rustic cottage has a moderate livi ...
From $237 per night (USD)VRBO
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Blue Moon Cottage, Islesboro
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Centrally located three bedroom rustic cottage. Bordered by golf course and nature trail. Large deck, ramp to front door ...
Click For PricingExpedia
From $120 per night (USD)VRBO
~ Cozy Cabin in the woods On Penobscot Bay Right Near the water ~
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a 300 square foot, one room, efficiency cabin. That Is Perfect For A Couple's Getaway On An Island In Maine! Se ...
From $120 per night (USD)VRBO
From $233 per night (USD)VRBO
Islesboro Island Maine Oceanfront Home on 12 Private Acres
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
PLEASE NOTE: Unless there is a last minute cancellation, the house is booked, or I am in it myself, through the summer ...
From $233 per night (USD)VRBO
From $197 per night (USD)VRBO
Penobscot Island Cabin, Waterfront Privacy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Privacy, magic, loon calls and your own beach. Wake to a sparkling sun on the water, sleep to a glittering Milky Way abo ...
From $197 per night (USD)VRBO
From $627 per night (USD)VRBO
The Anchorage, an oceanfront home with two private beaches on Islesboro Island
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
The Anchorage is a spectacular oceanfront peninsula property on Islesboro's eastern rocky coast overlooking Penobscot Ba ...
From $627 per night (USD)VRBO