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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
New place to stay
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
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 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
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, 8 reviews
Townhouse in Portland
Coastal Island Retreat in Diamond Cove, Casco Bay
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 3 Sept
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
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.98 out of 5 average rating, 82 reviews
Flat in Portland
Back Cove Retreat | Walk, Relax, Explore
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
New place to stay
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
27 Aug – 1 Sept
New place to stay
Top guest favourite
Home in Portland
Modern Peaks Island Getaway | Ocean Views + Decks
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Cabin in Yarmouth
Woodland Cottage
1 queen bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 11 reviews
Home in Portland
Island Home, Sleeps 5-8; Close to beach/ferry
6 bedrooms, 6 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Harpswell
Sunset Stunner w/summer dock
2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 35 reviews
Guest favourite
Home in Portland
Charming house near downtown and comfortable.
3 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Guest house in Chebeague Island
Wellhouse Cottage, A Peaceful Maine Getaway
1 bedroom, 1 double bed, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Tiny home in Scarborough
Southern Maine Tiny Home Cottage
1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov
5.0 out of 5 average rating, 76 reviews