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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
,
4.99 out of 5 average rating, 76 reviews
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
Home in Long Island
Spacious Long Island Retreat
4 bedrooms, 8 beds, 2 bathrooms
9–14 Sept
Superhost
Bed and breakfast in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Yurt in Chebeague Island
Yurt on Chebeague Island
4.98 out of 5 average rating, 190 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Superhost
Home in Portland
Gull Cottage: A Classic Peaks Island Charmer
3 bedrooms, 4 beds, 1 bathroom
6–13 Sept
Superhost
Home in Freeport
Casco Bay Beachfront Retreat
New place to stay, 3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
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
17–22 Jul
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
Top guest favourite
Treehouse in Pownal
The Copper Fox Treehouse
4.99 out of 5 average rating, 178 reviews, 1 bedroom, 3 beds, 1 bathroom
26–31 Aug
Top guest favourite
Home in Portland
Modern Peaks Island Getaway | Ocean Views + Decks
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 4 beds, 2 bathrooms
8–13 Oct
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
2 bedrooms, 6 beds, 1 bathroom
8–13 Aug
Home in Portland
Historic Island Retreat
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
Yurt in Portland
Sunrise Yurt on private island w/ a historic fort
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 3 beds, WC
21–26 Aug
Home in Phippsburg
Lovely 3-bedrom cottage with deep water dock.
3 bedrooms, 4 beds, 1 bathroom
18–23 Jul
Guest favourite
Loft in Harpswell
Oceanfront Studio w/ Private Dock in Harpswell!
5.0 out of 5 average rating, 7 reviews, 1 bed, 1 bathroom
21–26 Aug
Top guest favourite
Tiny home in Scarborough
Cozy Tiny Cottage • 9mi Portland • 6mi Beach
4.98 out of 5 average rating, 125 reviews, 1 bedroom, 2 beds, 1 bathroom
8–13 Nov
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
4.99 out of 5 average rating, 75 reviews, 3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Sept