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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
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4.99 out of 5 average rating, 76 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
Cottage in Long Island
Long Island Cottage: The Lobster Trap
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 79 reviews
Townhouse in Long Island
Maine Island Escape - close to Portland!
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
Guest favourite
Cottage in Long Island
A Once in a Lifetime Oceanfront Escape
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
1 bedroom, 1 queen bed, 1 bathroom
21–26 Aug
4.98 out of 5 average rating, 198 reviews
Top guest favourite
Home in Scarborough
Higgins Beach *New* Beach Home & Private Offices
3 bedrooms, 4 beds, 1.5 bathrooms
15–20 Dec
5.0 out of 5 average rating, 115 reviews
Flat in Portland
Back Cove Retreat | Walk, Relax, Explore
2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
New place to stay
Cottage in Portland
Spectacular Direct Oceanfront New Modern Home
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.7 out of 5 average rating, 20 reviews
Top guest favourite
Home in Cape Elizabeth
Pastoral Tranquil Walk to Trails Dining Shopping
3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Flat in South Portland
Forest City Oasis and Spa/Beaches/Portland/Pets!
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.98 out of 5 average rating, 83 reviews
Top guest favourite
Cottage in Portland
Casco-Vista, Island Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Portland
Modern Peaks Island Getaway | Ocean Views + Decks
2 bedrooms, 3 beds, 2 bathrooms
21–26 Nov
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.96 out of 5 average rating, 366 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
27 Aug – 1 Sept
New place to stay
Guest favourite
Home in Portland
Charming house near downtown and comfortable.
3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Portland
Quiet Comfy Victorian Escape
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 218 reviews
Top guest favourite
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews