Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Islesboro
Check in / Check out
Any week
Guests
Add guests
Become a host
Languages & currency
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Price filter
Type of place
Type of place filter
Show map
Search results; Over 1,000 homes in Islesboro
Over 1,000 homes in Islesboro
Top guest favourite
Guest favourite
Guest house in Islesboro
Milk House
Studio
,
·
1 bed
,
·
1 private bathroom
16–21 Oct
16–21 Oct
$1,180 SGD
$1,028 SGD
Show price breakdown
for 5 nights
,
·
4.97 out of 5 average rating, 67 reviews
4.97 (67)
Top guest favourite
Guest favourite
Cottage in Islesboro
Islesboro Boathouse
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$3,697 SGD
Show price breakdown
for 5 nights
$3,697 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 114 reviews
5.0 (114)
Top guest favourite
Guest favourite
Cottage in Islesboro
Beautiful Cottage on Island Bluff & Beach
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$4,263 SGD
Show price breakdown
for 5 nights
$4,263 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Home in Islesboro
Island Home
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
26 Sept – 3 Oct
26 Sept – 3 Oct
$5,819 SGD
Show price breakdown
for 7 nights
$5,819 SGD for 7 nights
Guest favourite
Guest favourite
Home in Islesboro
Charming Seaside Island Retreat
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
1–6 Dec
1–6 Dec
$3,249 SGD
Show price breakdown
for 5 nights
$3,249 SGD for 5 nights
Free cancellation
4.89 out of 5 average rating, 9 reviews
4.89 (9)
Guest favourite
Guest favourite
Home in Islesboro
The Colony
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
14–19 Sept
14–19 Sept
$2,463 SGD
$1,980 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Home in Islesboro
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
3.5 bathrooms
3.5 bathrooms
15–20 Sept
15–20 Sept
$4,033 SGD
Show price breakdown
for 5 nights
$4,033 SGD for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Guest favourite
Guest favourite
Home in Islesboro
Blue Moon Cottage
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
20–27 Sept
20–27 Sept
$1,700 SGD
$1,553 SGD
Show price breakdown
for 7 nights
Weekly discount
4.83 out of 5 average rating, 23 reviews
4.83 (23)
Home in Islesboro
Classic Maine Island Retreat
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2.5 bathrooms
2.5 bathrooms
28 Sept – 3 Oct
28 Sept – 3 Oct
$3,691 SGD
$3,234 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Islesboro
Newly built Scandinavian home
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
22–27 Sept
22–27 Sept
$7,071 SGD
Show price breakdown
for 5 nights
$7,071 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favourite
Guest favourite
Cottage in Islesboro
Ocean Front Island Cottage
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,236 SGD
Show price breakdown
for 5 nights
$1,236 SGD for 5 nights
Free cancellation
4.81 out of 5 average rating, 59 reviews
4.81 (59)
Top guest favourite
Guest favourite
Home in Islesboro
Island Retreat
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
15–20 Sept
15–20 Sept
$2,288 SGD
Show price breakdown
for 5 nights
$2,288 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Home in Islesboro
The Anchorage
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
18–23 Sept
18–23 Sept
$4,182 SGD
$3,764 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Home in Islesboro
3+ Bedroom on the water with dock.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
14–19 Sept
14–19 Sept
$4,631 SGD
Show price breakdown
for 5 nights
$4,631 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
17–22 Sept
17–22 Sept
$5,395 SGD
$4,768 SGD
Show price breakdown
for 5 nights
Guest favourite
Guest favourite
Cottage in Islesboro
Sweet, three bedroom cape on peaceful cove
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
17–22 Sept
17–22 Sept
$2,509 SGD
Show price breakdown
for 5 nights
$2,509 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 41 reviews
4.93 (41)
Top guest favourite
Guest favourite
Cottage in Islesboro
"The Dory" on Penobscot Bay, Mid-Coast Maine
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$2,390 SGD
$2,112 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 42 reviews
5.0 (42)
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
14–21 Sept
14–21 Sept
$5,751 SGD
Show price breakdown
for 7 nights
$5,751 SGD for 7 nights
4.86 out of 5 average rating, 22 reviews
4.86 (22)
Top guest favourite
Guest favourite
Guest house in Islesboro
Islesboro Island Oceanfront Cottage
1 bedroom
1 bedroom
,
·
2 single beds
2 single beds
,
·
1 bathroom
1 bathroom
26 Sept – 1 Oct
26 Sept – 1 Oct
$2,577 SGD
Show price breakdown
for 5 nights
$2,577 SGD for 5 nights
5.0 out of 5 average rating, 23 reviews
5.0 (23)
1
2
3
4
…
15
