Islesboro, Maine

Vacation Rentals in Islesboro, Maine

Discover 17 vacation rental properties in Islesboro. From 1 to 5 bedrooms. Average $407/night. 100% have pools.

17 verified listings Book securely on VRBO Prices updated March 2026

17 properties available

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

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

1 bath
PoolA/CWiFiBalcony
$75/night
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Island log home in Maine with ocean views

Island log home in Maine with ocean views

2 beds 1 bath
PoolA/CWiFiBalcony
$136/night
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~ Peaceful And Quaint Family Cottage On An Island In Maine ~

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

3 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...

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

1 bed 1 bath
PoolA/CWiFiBalcony
$225/night
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Blue Moon Cottage, Islesboro

Blue Moon Cottage, Islesboro

3 beds 2 baths
PoolA/CWiFiBalcony
$170/night
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Inchcliffe--Islesboro Island Waterfront Apartment

Inchcliffe--Islesboro Island Waterfront Apartment

1 bed 1 bath
PoolA/CWiFiBalcony
$196/night
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Waterside Island Cabin, rustic elegance w/beach NOTE: vaccination proof required

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

1 bed 1 bath
PoolA/CWiFiBalcony
$182/night
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Comfort & quiet on an island off the Maine Coast.

Comfort & quiet on an island off the Maine Coast.

2 beds 1 bath
PoolA/CWiFiBalcony
$226/night
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Charming Cottage on Island Bluff & Beach

Charming Cottage on Island Bluff & Beach

4 beds 1 bath
PoolA/CWiFiBalcony
$447/night
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Historic Seaside Cottage with its own beaches overlooking Penobscot Bay..

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

3 beds 1 bath
PoolA/CWiFiBalcony
$324/night
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Surrounded by Water . . . A Very Special Place

Surrounded by Water . . . A Very Special Place

4 beds 1 bath
PoolA/CWiFiBalcony
$271/night
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"The Dory" on Penobscot Bay, Mid-Coast Maine

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

2 beds 1 bath
PoolA/CWiFiBalcony
$321/night
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Islesboro's Seaglass Farm

Islesboro's Seaglass Farm

4 beds 2 baths
PoolA/CWiFiBalcony
$2,511/night
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MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

5 beds 3 baths
PoolA/CWiFiBalcony
$517/night
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Take a Ferry to the Island of Your Dreams.

Take a Ferry to the Island of Your Dreams.

3 beds 1 bath
PoolA/CWiFiBalcony
$387/night
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The Sea Box Island Retreat. Enjoy ocean views with wooded privacy

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

3 beds 1 bath
PoolA/CWiFiBalcony
$427/night
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Sweet three bedroom Cape on peaceful cove

Sweet three bedroom Cape on peaceful cove

3 beds 2 baths
PoolA/CWiFiBalcony
$301/night
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