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Search results; Over 1,000 homes in Long Island

Guest favourite
Home in Long Island
Magical Long Island Retreat | Steps to Quiet Beach
7 bedrooms, 5.5 private bathrooms
24–29 Sept
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4.93 out of 5 average rating, 29 reviews
Home in Long Island
500Island
4 bedrooms, 5 beds, 2.5 bathrooms
22–29 Sept
Guest favourite
Cottage in Long Island
Picturesque Maine water view Long Island
4 bedrooms, 5 beds, 1 bathroom
27 Sept – 4 Oct
4.82 out of 5 average rating, 51 reviews
Townhouse in Long Island
Maine Island Escape - close to Portland!
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Long Island
A Once in a Lifetime Oceanfront Escape
2 bedrooms, 3 beds, 1 bathroom
16–22 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Yarmouth
Beautiful home on Broad Cove
4 bedrooms, 4 beds, 3.5 bathrooms
17–22 Sept
Top guest favourite
Home in Portland
Cheerful, Sunny, 3 Bedroom Island Home
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 67 reviews
Top guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 75 reviews
Guest favourite
Home in Portland
BELLA VISTA - DIRECT OCEANFRONT at Elm Cove
3 bedrooms, 5 beds, 2.5 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 27 reviews
Home in Portland
Island Home, Sleeps 5-8; Close to beach/ferry
6 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Place to stay in Portland
Carrabassett Lodge
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 141 reviews
Guest favourite
Home in Portland
Unbeatable view! Peaceful spot.
4 bedrooms, 2 double beds, 2 bathrooms
7–12 Oct
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Portland
Classic Charm, Ocean View
5 bedrooms, 7 beds, 2 bathrooms
28 Sept – 3 Oct
Top guest favourite
Home in Portland
The Island House
3 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Cape Elizabeth
"Periwinkle" ~ a Charming Oceanfront Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
1–7 Apr
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Cottage in Portland
Casco-Vista, Island Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 29 reviews
Home in Portland
Historic Island Retreat | Pool, Beaches & Ferry
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Sept
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
18–23 Dec
4.98 out of 5 average rating, 89 reviews
Top guest favourite
Home in Portland
"The Cottage" on Peaks Island
3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
4.9 out of 5 average rating, 100 reviews