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
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
Photo 1 of 17
Top guest favourite
Guest favourite
Cottage in Islesboro
Islesboro Boathouse
1 bedroom
,
·
1 bed
,
·
1 private bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$3,145 SGD
Show price breakdown
for 5 nights
$3,145 SGD for 5 nights
,
·
5.0 out of 5 average rating, 114 reviews
5.0 (114)
Photo 1 of 29
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
$5,834 SGD
Show price breakdown
for 7 nights
$5,834 SGD for 7 nights
Photo 1 of 29
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
22–27 Sept
22–27 Sept
$4,274 SGD
Show price breakdown
for 5 nights
$4,274 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Photo 1 of 29
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
$3,938 SGD
Show price breakdown
for 5 nights
$3,938 SGD for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Photo 1 of 29
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
$3,170 SGD
Show price breakdown
for 5 nights
$3,170 SGD for 5 nights
Free cancellation
4.89 out of 5 average rating, 9 reviews
4.89 (9)
Photo 1 of 23
Guest favourite
Guest favourite
Cottage in Islesboro
Ocean Front Island Cottage
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
22–27 Sept
22–27 Sept
$1,202 SGD
Show price breakdown
for 5 nights
$1,202 SGD for 5 nights
4.82 out of 5 average rating, 60 reviews
4.82 (60)
Photo 1 of 25
Guest favourite
Guest favourite
Home in Islesboro
The Colony
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
15–20 Sept
15–20 Sept
$2,492 SGD
$2,004 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 29
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
$3,700 SGD
$3,232 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
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
$1,468 SGD
$1,321 SGD
Show price breakdown
for 7 nights
Weekly discount
4.83 out of 5 average rating, 23 reviews
4.83 (23)
Photo 1 of 29
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
$7,089 SGD
Show price breakdown
for 5 nights
$7,089 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Islesboro
Island Retreat
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
16–21 Sept
16–21 Sept
$2,293 SGD
Show price breakdown
for 5 nights
$2,293 SGD for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Photo 1 of 29
Home in Islesboro
The Anchorage
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
18–23 Sept
18–23 Sept
$4,193 SGD
$3,773 SGD
Show price breakdown
for 5 nights
Photo 1 of 29
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
18–23 Sept
18–23 Sept
$5,408 SGD
$4,779 SGD
Show price breakdown
for 5 nights
Photo 1 of 29
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
21–26 Sept
21–26 Sept
$2,470 SGD
$2,180 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 42 reviews
5.0 (42)
Photo 1 of 29
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
15–20 Sept
15–20 Sept
$3,954 SGD
Show price breakdown
for 5 nights
$3,954 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Photo 1 of 22
Top guest favourite
Guest favourite
Guest house in Islesboro
Milk House
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
16–21 Oct
16–21 Oct
$1,183 SGD
$1,031 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 67 reviews
4.97 (67)
Photo 1 of 15
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
18–23 Sept
18–23 Sept
$2,516 SGD
Show price breakdown
for 5 nights
$2,516 SGD for 5 nights
4.93 out of 5 average rating, 41 reviews
4.93 (41)
Photo 1 of 20
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
15–22 Sept
15–22 Sept
$4,891 SGD
Show price breakdown
for 7 nights
$4,891 SGD for 7 nights
4.86 out of 5 average rating, 22 reviews
4.86 (22)
Photo 1 of 29
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
$2,192 SGD
Show price breakdown
for 5 nights
$2,192 SGD for 5 nights
5.0 out of 5 average rating, 23 reviews
5.0 (23)
1
2
3
4
…
15
