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Islesboro Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
18 rentals in Islesboro.
Island log home in Maine with ocean views, vacation rental in Islesboro
Island log home in Maine with ocean views, vacation rental in Islesboro
Island log home in Maine with ocean views, vacation rental in Islesboro

Island log home in Maine with ocean views

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Inchcliffe--Islesboro Island Waterfront Apartment, vacation rental in Islesboro
Inchcliffe--Islesboro Island Waterfront Apartment, vacation rental in Islesboro
Inchcliffe--Islesboro Island Waterfront Apartment, vacation rental in Islesboro

Inchcliffe--Islesboro Island Waterfront Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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~ Cozy Cabin in the woods On Penobscot Bay Right Near the water ~, vacation rental in Islesboro
~ Cozy Cabin in the woods On Penobscot Bay Right Near the water ~, vacation rental in Islesboro
~ Cozy Cabin in the woods On Penobscot Bay Right Near the water ~, vacation rental in Islesboro

~ Cozy Cabin in the woods On Penobscot Bay Right Near the water ~

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast..., vacation rental in Islesboro
Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast..., vacation rental in Islesboro
Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast..., vacation rental in Islesboro

Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterside Island Cabin, rustic elegance w/beach NOTE: vaccination proof required, vacation rental in Islesboro
Waterside Island Cabin, rustic elegance w/beach NOTE: vaccination proof required, vacation rental in Islesboro
Waterside Island Cabin, rustic elegance w/beach NOTE: vaccination proof required, vacation rental in Islesboro

Waterside Island Cabin, rustic elegance w/beach NOTE: vaccination proof required

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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"The Dory" on Penobscot Bay, Mid-Coast Maine, vacation rental in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine, vacation rental in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine, vacation rental in Islesboro

"The Dory" on Penobscot Bay, Mid-Coast Maine

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfort & quiet on an island off the Maine Coast., vacation rental in Islesboro
Comfort & quiet on an island off the Maine Coast., vacation rental in Islesboro
Comfort & quiet on an island off the Maine Coast., vacation rental in Islesboro

Comfort & quiet on an island off the Maine Coast.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sweet three bedroom Cape on peaceful cove, vacation rental in Islesboro
Sweet three bedroom Cape on peaceful cove, vacation rental in Islesboro
Sweet three bedroom Cape on peaceful cove, vacation rental in Islesboro

Sweet three bedroom Cape on peaceful cove

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Seaside Cottage with its own beaches overlooking Penobscot Bay.., vacation rental in Islesboro
Historic Seaside Cottage with its own beaches overlooking Penobscot Bay.., vacation rental in Islesboro
Historic Seaside Cottage with its own beaches overlooking Penobscot Bay.., vacation rental in Islesboro

Historic Seaside Cottage with its own beaches overlooking Penobscot Bay..

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming Waterfront Cottage Just Steps from East Penobscot Bay, vacation rental in Islesboro
Charming Waterfront Cottage Just Steps from East Penobscot Bay, vacation rental in Islesboro
Charming Waterfront Cottage Just Steps from East Penobscot Bay, vacation rental in Islesboro

Charming Waterfront Cottage Just Steps from East Penobscot Bay

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach-Side Cottage: Windows By The Sea, vacation rental in Islesboro
Beach-Side Cottage: Windows By The Sea, vacation rental in Islesboro
Beach-Side Cottage: Windows By The Sea, vacation rental in Islesboro

Beach-Side Cottage: Windows By The Sea

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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~ Peaceful And Quaint Family Cottage On An Island In Maine ~, vacation rental in Islesboro
~ Peaceful And Quaint Family Cottage On An Island In Maine ~, vacation rental in Islesboro
~ Peaceful And Quaint Family Cottage On An Island In Maine ~, vacation rental in Islesboro

~ Peaceful And Quaint Family Cottage On An Island In Maine ~

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Take a Ferry to the Island of Your Dreams., vacation rental in Islesboro
Take a Ferry to the Island of Your Dreams., vacation rental in Islesboro
Take a Ferry to the Island of Your Dreams., vacation rental in Islesboro

Take a Ferry to the Island of Your Dreams.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Surrounded by Water . . . A Very Special Place, vacation rental in Islesboro
Surrounded by Water . . . A Very Special Place, vacation rental in Islesboro
Surrounded by Water . . . A Very Special Place, vacation rental in Islesboro

Surrounded by Water . . . A Very Special Place

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Sea Box Island Retreat. Enjoy ocean views with wooded  privacy, vacation rental in Islesboro
The Sea Box Island Retreat. Enjoy ocean views with wooded  privacy, vacation rental in Islesboro
The Sea Box Island Retreat. Enjoy ocean views with wooded  privacy, vacation rental in Islesboro

The Sea Box Island Retreat. Enjoy ocean views with wooded privacy

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Cottage on Island Bluff & Beach, vacation rental in Islesboro
Charming Cottage on Island Bluff & Beach, vacation rental in Islesboro
Charming Cottage on Island Bluff & Beach, vacation rental in Islesboro

Charming Cottage on Island Bluff & Beach

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Islesboro Island Maine Oceanfront Home on 12 Private Acres, vacation rental in Islesboro
Islesboro Island Maine Oceanfront Home on 12 Private Acres, vacation rental in Islesboro
Islesboro Island Maine Oceanfront Home on 12 Private Acres, vacation rental in Islesboro

Islesboro Island Maine Oceanfront Home on 12 Private Acres

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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MASSIVE Oceanfront Dark Harbor Home on ISLESBORO, vacation rental in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO, vacation rental in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO, vacation rental in Islesboro

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

Rental Home
5 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Showing results 1-18 of 18
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