Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
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
Type of place
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
Islesboro Island Oceanfront Cottage
1 bedroom
,
·
2 beds
,
·
1 private bathroom
31 Aug – 5 Sept
31 Aug – 5 Sept
$2,604 SGD
Show price breakdown
for 5 nights
$2,604 SGD for 5 nights
,
·
5.0 out of 5 average rating, 22 reviews
5.0 (22)
Top guest favourite
Guest favourite
Cottage in Islesboro
Islesboro Boathouse
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$3,736 SGD
Show price breakdown
for 5 nights
$3,736 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 113 reviews
5.0 (113)
Top guest favourite
Guest favourite
Guest house in Islesboro
Milk House
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
11–16 Sept
11–16 Sept
$1,039 SGD
Show price breakdown
for 5 nights
$1,039 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 64 reviews
4.97 (64)
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
27 Aug – 1 Sept
27 Aug – 1 Sept
$4,272 SGD
Show price breakdown
for 5 nights
$4,272 SGD for 5 nights
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favourite
Guest favourite
Villa in Islesboro
Bounty Cove Getaway and Private Nature Preserve
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
,
·
5 bathrooms
5 bathrooms
24–29 Aug
24–29 Aug
$15,319 SGD
Show price breakdown
for 5 nights
$15,319 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 9 reviews
5.0 (9)
Home in Islesboro
The Anchorage
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
11–16 Sept
11–16 Sept
$4,339 SGD
Show price breakdown
for 5 nights
$4,339 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Cottage in Islesboro
Surrounded by Water
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
13–20 Sept
13–20 Sept
$3,358 SGD
Show price breakdown
for 7 nights
$3,358 SGD for 7 nights
5.0 out of 5 average rating, 9 reviews
5.0 (9)
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
9–14 Sept
9–14 Sept
$2,566 SGD
Show price breakdown
for 5 nights
$2,566 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 39 reviews
4.92 (39)
Flat in Islesboro
The Roost
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
15–20 Aug
15–20 Aug
$1,781 SGD
Show price breakdown
for 5 nights
$1,781 SGD for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Home in Islesboro
Island Retreat
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
7–12 Sept
7–12 Sept
$2,312 SGD
Show price breakdown
for 5 nights
$2,312 SGD for 5 nights
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Home in Islesboro
Classic Maine Island Retreat
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2.5 bathrooms
2.5 bathrooms
14–19 Aug
14–19 Aug
$3,343 SGD
Show price breakdown
for 5 nights
$3,343 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
16–22 Aug
16–22 Aug
$5,808 SGD
Show price breakdown
for 6 nights
$5,808 SGD for 6 nights
Free cancellation
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
$3,283 SGD
Show price breakdown
for 5 nights
$3,283 SGD for 5 nights
4.83 out of 5 average rating, 6 reviews
4.83 (6)
Home in Islesboro
3+ Bedroom on the water with dock.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
21–26 Aug
21–26 Aug
$4,742 SGD
Show price breakdown
for 5 nights
$4,742 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
7–12 Sept
7–12 Sept
$2,489 SGD
$2,198 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 38 reviews
5.0 (38)
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
7–12 Sept
7–12 Sept
$5,773 SGD
Show price breakdown
for 5 nights
$5,773 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
26 Aug – 2 Sept
26 Aug – 2 Sept
$1,791 SGD
$1,637 SGD
Show price breakdown
for 7 nights
Weekly discount
4.82 out of 5 average rating, 22 reviews
4.82 (22)
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
23–30 Aug
23–30 Aug
$5,811 SGD
Show price breakdown
for 7 nights
$5,811 SGD for 7 nights
Free cancellation
4.86 out of 5 average rating, 21 reviews
4.86 (21)
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
$7,145 SGD
Show price breakdown
for 5 nights
$7,145 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
1
2
3
4
…
15
