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Search results; Over 1,000 homes in Long Island

Superhost
Cottage in Long Island
Maine island vacation cottage
3 bedrooms, 4 beds, 1.5 private bathrooms
31 Aug – 7 Sept
,
4.62 out of 5 average rating, 60 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
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
Home in Long Island
Spacious Long Island Retreat
4 bedrooms, 8 beds, 2 bathrooms
9–14 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
Home in Portland
Historic Island Retreat
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
Top guest favourite
Room in Falmouth
Green Room at Foreside Farmhouse
4.99 out of 5 average rating, 89 reviews, 1 bed, 1.5 bathrooms
26–31 Jul
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Oct
Superhost
Home in Portland
Gull Cottage: A Classic Peaks Island Charmer
3 bedrooms, 4 beds, 1 bathroom
6–13 Sept
Top guest favourite
Cottage in Portland
Captain's Quarters on Peaks Island
4.98 out of 5 average rating, 40 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Jan
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
Top guest favourite
Guest suite in South Portland
Oceanfront with amazing views and private entrance
4.99 out of 5 average rating, 894 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Dec
Top guest favourite
Room in South Portland
Peaceful Wooded Oasis Near Portland & Beaches
4.98 out of 5 average rating, 109 reviews, 1 queen bed, 1.5 bathrooms
2–7 Aug
Guest favourite
Home in Peaks Island
Peaks Island, Maine, Northcliffe Cottage
4.83 out of 5 average rating, 18 reviews, 3 bedrooms, 5 beds, 1 bathroom
6–13 Sept
Top guest favourite
Room in Freeport
Limoges - A short walk to shops and has Wifi
4.99 out of 5 average rating, 215 reviews, 1 queen bed, 1.5 bathrooms
9–14 Aug
Top guest favourite
Cottage in Portland
Casco-Vista, Island Cottage
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
Guest favourite
Flat in Portland
1-bedroom unit (3 beds) with free parking
4.96 out of 5 average rating, 143 reviews, 1 bedroom, 3 beds, 1 bathroom
1–6 Nov
Top guest favourite
Home in Portland
Wall St. Retreat: Family-Ready Portland Home
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct