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Search results; Over 1,000 homes in Islesboro

Top guest favourite

Guest house in Islesboro

Islesboro Island Oceanfront Cottage

1 bedroom, 2 beds, 1 private bathroom

20–25 Jul

$2,633 SGD for 5 nights

,

5.0 out of 5 average rating, 19 reviews

Top guest favourite

Guest house in Islesboro

Milk House

1 queen bed

30 Jul – 4 Aug

$1,050 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 54 reviews

Top guest favourite

Home in Islesboro

Island Retreat

3 bedrooms, 3 beds

17–22 Jul

$2,175 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Cottage in Islesboro

Islesboro Boathouse

1 bedroom, 1 bed

26–31 Oct

$3,777 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 111 reviews

Home in Islesboro

Charming Seaside Island Retreat

5 bedrooms, 7 beds

8–13 Aug

$3,319 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Cottage in Islesboro

Beautiful Cottage on Island Bluff & Beach

4 bedrooms, 5 beds

23–30 Aug

$6,440 SGD for 7 nights

5.0 out of 5 average rating, 12 reviews

Guest favourite

Cottage in Islesboro

Surrounded by Water

4 bedrooms, 6 beds

13–20 Sept

$3,395 SGD for 7 nights

5.0 out of 5 average rating, 7 reviews

Guest favourite

Villa in Islesboro

Bounty Cove Getaway and Private Nature Preserve

5 bedrooms, 8 beds

24–29 Aug

$15,488 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

Guest favourite

Cottage in Islesboro

Sweet, three bedroom cape on peaceful cove

3 bedrooms, 3 beds

9–14 Sept

$2,594 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 38 reviews

Guest favourite

Home in Islesboro

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO

5 bedrooms, 7 beds

7–12 Sept

$5,837 SGD for 5 nights

5.0 out of 5 average rating, 26 reviews

Top guest favourite

Cottage in Islesboro

"The Dory" on Penobscot Bay, Mid-Coast Maine

2 bedrooms, 3 beds

20–25 Aug

5.0 out of 5 average rating, 34 reviews

Top guest favourite

Tiny home in Islesboro

"Boho Bungalow" Studio Island Guest Cottage

1 bedroom, 1 sofa bed

8–13 Aug

$1,320 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 38 reviews

Home in Islesboro

3+ Bedroom on the water with dock.

3 bedrooms, 3 beds

21–26 Aug

$3,598 SGD for 5 nights

Home in Islesboro

The Anchorage

4 bedrooms, 5 beds

11–16 Sept

$4,387 SGD for 5 nights

Free cancellation

Home in Islesboro

FoxGlove Farm on Islesboro

4 bedrooms, 5 beds

9–15 Aug

$6,028 SGD for 6 nights

Free cancellation

Home in Islesboro

Charming 4 BR Farmhouse w/ Beach

4 bedrooms, 7 beds

17–24 Aug

$5,875 SGD for 7 nights

Free cancellation

4.86 out of 5 average rating, 21 reviews

Home in Islesboro

Island Home

5 bedrooms, 6 beds

15–22 Aug

$5,799 SGD for 7 nights

Home in Islesboro

Newly built Scandinavian home

3 bedrooms, 3 beds

7–12 Sept

$7,223 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Home in Islesboro

Classic Maine Island Retreat

4 bedrooms, 7 beds

22–27 Jul

$3,384 SGD for 5 nights