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Search results; Over 1,000 homes in Peaks Island, Portland

Top guest favourite

Room in Peaks Island

Island Room with a View

1 bedroom, 1 bed, 1 shared bathroom

4–9 Jul

$1,587 SGD for 5 nights

,

4.97 out of 5 average rating, 108 reviews

Top guest favourite

Home in Portland

Sea Glass - Peaks Island backshore oceanfront

3 bedrooms, 5 beds, 2 bathrooms

29 Aug – 5 Sept

$8,297 SGD for 7 nights

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Home in Portland

Ocean View Cottage on Peaks Island

2 bedrooms, 3 beds, 1 bathroom

1–6 Sept

5.0 out of 5 average rating, 72 reviews

Top guest favourite

Flat in Portland

Peaks Island Master Bedroom Suite

1 bedroom, 2 beds, 1 bathroom

30 Aug – 4 Sept

$1,477 SGD for 5 nights

4.99 out of 5 average rating, 218 reviews

Superhost

Bed and breakfast in Portland

Aerie 2 reg:STHR-007375-2025 Peaks Island, Me

1 bedroom, 1 bed, 1 bathroom

14–19 Jul

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Portland

Little Island Cottage

3 bedrooms, 3 beds, 1 bathroom

23–28 Aug

$1,827 SGD for 5 nights

4.96 out of 5 average rating, 25 reviews

Guest favourite

Home in Portland

Peaks Island Oceanfront Escape: Private Pool & A/C

4 bedrooms, 5 beds, 4.5 bathrooms

23–30 Aug

$17,468 SGD for 7 nights

5.0 out of 5 average rating, 11 reviews

Guest favourite

Holiday home in Portland

Heron's Perch on Peaks' Island

4 bedrooms, 8 beds, 2 bathrooms

25–30 Jul

$5,709 SGD for 5 nights

4.95 out of 5 average rating, 39 reviews

Top guest favourite

Home in Portland

The Island House

3 bedrooms, 5 beds, 1.5 bathrooms

29 Aug – 3 Sept

$5,616 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Cottage in Portland

Casco-Vista, Island Cottage

3 bedrooms, 3 beds, 1.5 bathrooms

6–11 Sept

$3,007 SGD for 5 nights

5.0 out of 5 average rating, 22 reviews

Guest favourite

Cottage in Portland

Porches @ Peaks Island

3 bedrooms, 3 beds, 1.5 bathrooms

28 Sept – 3 Oct

$3,098 SGD for 5 nights

4.9 out of 5 average rating, 67 reviews

Guest favourite

Flat in Portland

Peaks Island Casco Bay View Condo w/ Beach Access

2 bedrooms, 3 beds, 1 bathroom

14–19 Jul

5.0 out of 5 average rating, 9 reviews

Guest favourite

Home in Portland

BELLA VISTA - DIRECT OCEANFRONT at Elm Cove

3 bedrooms, 5 beds, 2.5 bathrooms

8–15 Aug

$8,274 SGD for 7 nights

4.96 out of 5 average rating, 26 reviews

Guest favourite

Cottage in Portland

Peaks Island Waterfront

1 bedroom, 1 double bed, 1 bathroom

30 Aug – 4 Sept

$2,779 SGD for 5 nights

4.93 out of 5 average rating, 117 reviews

Top guest favourite

Home in Portland

Modern Peaks Island Getaway | Ocean Views + Decks

2 bedrooms, 4 beds, 2 bathrooms

8–13 Oct

$5,929 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Cottage in Portland

Classic Peaks Island Cottage - 5 min walk to Ferry

3 bedrooms, 4 beds, 1 bathroom

27 Aug – 1 Sept

$3,983 SGD for 5 nights

5.0 out of 5 average rating, 68 reviews

Top guest favourite

Home in Portland

Ocean Paradise Sunrise/Sunset Peaks Portland

2 bedrooms, 3 beds, 1.5 bathrooms

26 Jul – 2 Aug

$10,540 SGD for 7 nights

5.0 out of 5 average rating, 81 reviews

Top guest favourite

Flat in Peaks Island

Beach Front, Waterfront, Ferry Beach

2 bedrooms, 3 beds, 1 bathroom

29 Aug – 5 Sept

Weekly discount

5.0 out of 5 average rating, 44 reviews

Guest favourite

Home in Portland

Stunning Ocean Views From This Peaks Island Home

3 bedrooms, 5 beds, 2 bathrooms

30 Aug – 4 Sept

4.9 out of 5 average rating, 119 reviews