Islesboro Island Rentals
From $225 per night (USD)VRBO
Comfort & quiet on an island off the Maine Coast.
- Bedrooms:
- 2
- 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 $225 per night (USD)VRBO
From $350 per night (USD)VRBO
Beach-Side Cottage: Windows By The Sea
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Secluded down a dead-end dirt road, our beach-side cottage sits in the lap of a beautiful sand and pebble beach, so clos ...
From $350 per night (USD)VRBO
From $135 per night (USD)VRBO
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 $135 per night (USD)VRBO
From $207 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 $207 per night (USD)VRBO
From $317 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 $317 per night (USD)VRBO
From $225 per night (USD)Expedia
Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 16' x 24' cabin sits on eleven acres of ocean frontage at 105 feet above sea level (one of the highest points on Is ...
From $225 per night (USD)Expedia
From $200 per night (USD)VRBO
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
- Bedrooms:
- 2
- 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 $200 per night (USD)VRBO
From $600 per night (USD)VRBO
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and c ...
From $600 per night (USD)VRBO
From $300 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 $300 per night (USD)VRBO
From $300 per night (USD)VRBO
Charming Waterfront Cottage Just Steps from East Penobscot Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
2 WEEK MINIMUM RENTAL. Stay in a charming oceanfront cottage on 4 wooded acres just feet from the beach. Enjoy morni ...
From $300 per night (USD)VRBO
From $172 per night (USD)VRBO
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 ...
From $172 per night (USD)VRBO
From $214 per night (USD)VRBO
Islesboro Island Maine Oceanfront Home on 12 Private Acres
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
PLEASE NOTE: The house is booked or I am in it myself through the summer and into mid-October, 2024. Generally I know ...
From $214 per night (USD)VRBO
From $385 per night (USD)VRBO
Take a Ferry to the Island of Your Dreams.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your vacation home - a barn style summer home on Broad Cove near the ferry. Imagine yourself relaxing on the ...
From $385 per night (USD)VRBO
From $450 per night (USD)VRBO
Charming Cottage on Island Bluff & Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 1880s cottage on a high bluff with 180 degree views of East Penobscot Bay overlooking its own private beach in ...
From $450 per night (USD)VRBO
From $185 per night (USD)VRBO
Waterside Island Cabin, rustic elegance w\/beach NOTE: vaccination proof required
- 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 $185 per night (USD)VRBO
From $75 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 $75 per night (USD)VRBO
From $425 per night (USD)VRBO
The Sea Box Island Retreat. Enjoy ocean views with wooded privacy
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Take the Islesboro ferry from Lincolnville ME to the idyllic Islesboro community. Walk to the beach, tennis or pickle b ...
From $425 per night (USD)VRBO
From $2500 per night (USD)Expedia
Islesboro's Seaglass Farm
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Charming 1801 cape Farm house on 3 acres of woods, fields and lawn on the island of Islesboro. Throughly modern home wit ...
From $2500 per night (USD)Expedia
From $300 per night (USD)VRBO
Sweet three bedroom Cape on peaceful cove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This three bedroom, two bath cape was built by an islander in the 1970s. This well-built house is an easy house to live ...
From $300 per night (USD)VRBO
From $433 per night (USD)VRBO
Surrounded by Water . . . A Very Special Place
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
***2023 July/August availability will be released mid-Oct 2022*** Many people have told us that our home is one of the ...
From $433 per night (USD)VRBO