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Search results; Over 1,000 homes in Long Island

Guest favourite
Home in Long Island
Whole house on a great island in Casco Bay!
3 bedrooms, 4 beds, 2 private bathrooms
7–12 Sept
,
4.99 out of 5 average rating, 76 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds
23–30 Aug
New place to stay
Townhouse in Long Island
Maine Island Escape - close to Portland!
3 bedrooms, 4 beds
7–12 Sept
Guest favourite
Cottage in Long Island
A Once in a Lifetime Oceanfront Escape
2 bedrooms, 3 beds
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Portland
Casco-Vista, Island Cottage
3 bedrooms, 3 beds
6–11 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Scarborough
Higgins Beach *New* Beach Home & Private Offices
3 bedrooms, 4 beds
15–20 Dec
5.0 out of 5 average rating, 115 reviews
Top guest favourite
Home in Portland
Ocean Paradise Sunrise/Sunset Peaks Portland
2 bedrooms, 3 beds
19–24 Aug
5.0 out of 5 average rating, 84 reviews
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds
18–23 Oct
4.98 out of 5 average rating, 82 reviews
Top guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Harpswell
Sunset Stunner w/summer dock
2 bedrooms, 2 beds
25–30 Oct
4.97 out of 5 average rating, 35 reviews
Cottage in Portland
Spectacular Direct Oceanfront New Modern Home
3 bedrooms, 4 beds
7–12 Sept
4.7 out of 5 average rating, 20 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds
27 Aug – 1 Sept
New place to stay
Flat in Yarmouth
The Royal Retreat.
2 bedrooms, 2 queen beds
9–14 Oct
Guest favourite
Home in Portland
Charming house near downtown and comfortable.
3 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 5 reviews
Townhouse in Portland
Coastal Island Retreat in Diamond Cove, Casco Bay
3 bedrooms, 4 beds
29 Aug – 3 Sept
Guest favourite
Cabin in Portland
Sequester on Peaks Island
1 bedroom, 2 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Portland
Modern Peaks Island Getaway | Ocean Views + Decks
2 bedrooms, 3 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
2 bedrooms, 3 beds
23–30 Aug
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Tiny home in Freeport
Cozy Rock Cabin #thewaylifeshouldbe
2 bedrooms, 2 beds
28 Aug – 2 Sept
4.99 out of 5 average rating, 386 reviews