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Search results; Over 1,000 homes in Long Island

Superhost
Cottage in Long Island
Grace Cottage
2 bedrooms, 5 beds, 2 private bathrooms
6–11 Sept
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4.91 out of 5 average rating, 46 reviews
Home in Long Island
500Island
New place to stay, 4 bedrooms, 5 beds, 2.5 bathrooms
23–30 Aug
Guest favourite
Cottage in Long Island
A Once in a Lifetime Oceanfront Escape
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
Guest favourite
Cottage in Portland
Peaks Island Waterfront
4.93 out of 5 average rating, 118 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Portland
Island Getaway, Short ferry ride to Portland
5.0 out of 5 average rating, 23 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Sept
Guest favourite
Flat in South Portland
Peaceful & minutes from Old Port w/private parking
4.9 out of 5 average rating, 82 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Home in Portland
Modern Peaks Island Getaway | Ocean Views + Decks
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 2 bathrooms
21–26 Nov
Superhost
Room in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
5.0 out of 5 average rating, 4 reviews, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Guest suite in Falmouth
Pristine Waterfront Studio Apt. Retreat
4.94 out of 5 average rating, 266 reviews, 2 beds, 1 bathroom
22–27 Aug
Guest favourite
Flat in South Portland
Cozy SoPo Condo
4.99 out of 5 average rating, 142 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Room in Peaks Island
Island Room with a View
4.97 out of 5 average rating, 108 reviews, 1 double bed, 1 bathroom
7–12 Aug
Top guest favourite
Flat in Portland
Stylish Condo in Downtown Portland w/ Private Yard
5.0 out of 5 average rating, 23 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Home in Long Island
Spacious Long Island Retreat
4 bedrooms, 8 beds, 2 bathrooms
9–14 Sept
Top guest favourite
Room in South Portland
Suite at a convenient location; near Old Port.
4.94 out of 5 average rating, 52 reviews, 1 king bed, 1 bathroom
1–6 Nov
Top guest favourite
Cottage in Harpswell
Cottage with Ocean Views on Pott’s Point
4.97 out of 5 average rating, 39 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Flat in Portland
Urban Seaside Retreat- East End Overlook Casco Bay
4.98 out of 5 average rating, 156 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in Falmouth
Poolside Suite-Gateway to Portland
4.98 out of 5 average rating, 121 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Oct
Superhost
Cottage in Harpswell
The Red House - Waterfront cottage with AC!
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Aug
Superhost
Home in Portland
Gull Cottage: A Classic Peaks Island Charmer
3 bedrooms, 4 beds, 1 bathroom
6–13 Sept