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
20–25 Jul
20–25 Jul
$2,627 SGD
Show price breakdown
for 5 nights
$2,627 SGD for 5 nights
,
·
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Top guest favourite
Guest favourite
Guest house in Islesboro
Milk House
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
30 Jul – 4 Aug
30 Jul – 4 Aug
$1,048 SGD
Show price breakdown
for 5 nights
$1,048 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 54 reviews
4.96 (54)
Top guest favourite
Guest favourite
Cottage in Islesboro
Islesboro Boathouse
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
26–31 Oct
26–31 Oct
$3,770 SGD
Show price breakdown
for 5 nights
$3,770 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 111 reviews
5.0 (111)
Top guest favourite
Guest favourite
Home in Islesboro
Island Retreat
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
2–7 Aug
2–7 Aug
$2,300 SGD
Show price breakdown
for 5 nights
$2,300 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
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
23–30 Aug
23–30 Aug
$6,427 SGD
Show price breakdown
for 7 nights
$6,427 SGD for 7 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Home in Islesboro
Classic Maine Island Retreat
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2.5 bathrooms
2.5 bathrooms
22–27 Jul
22–27 Jul
$3,804 SGD
Show price breakdown
for 5 nights
$3,804 SGD for 5 nights
Home in Islesboro
Charming Seaside Island Retreat
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
8–13 Aug
8–13 Aug
$3,313 SGD
Show price breakdown
for 5 nights
$3,313 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
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
$15,457 SGD
Show price breakdown
for 5 nights
$15,457 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Home in Islesboro
The Anchorage
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
11–16 Sept
11–16 Sept
$4,379 SGD
Show price breakdown
for 5 nights
$4,379 SGD for 5 nights
Free cancellation
Home in Islesboro
Charming 4 BR Farmhouse w/ Beach
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
17–24 Aug
17–24 Aug
$5,863 SGD
Show price breakdown
for 7 nights
$5,863 SGD for 7 nights
Free cancellation
4.86 out of 5 average rating, 21 reviews
4.86 (21)
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
$5,825 SGD
Show price breakdown
for 5 nights
$5,825 SGD for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
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 Aug
20–25 Aug
$2,587 SGD
$2,282 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 34 reviews
5.0 (34)
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
$3,605 SGD
Show price breakdown
for 5 nights
$3,605 SGD for 5 nights
Home in Islesboro
FoxGlove Farm on Islesboro
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
9–15 Aug
9–15 Aug
$6,016 SGD
Show price breakdown
for 6 nights
$6,016 SGD for 6 nights
Free cancellation
Top guest favourite
Guest favourite
Tiny home in Islesboro
"Boho Bungalow" Studio Island Guest Cottage
1 bedroom
1 bedroom
,
·
1 sofa bed
1 sofa bed
,
·
1 bathroom
1 bathroom
8–13 Aug
8–13 Aug
$1,318 SGD
Show price breakdown
for 5 nights
$1,318 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 38 reviews
4.97 (38)
Home in Islesboro
Newly built Scandinavian home
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
$7,209 SGD
Show price breakdown
for 5 nights
$7,209 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Home in Islesboro
Island Home
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
15–22 Aug
15–22 Aug
$5,787 SGD
Show price breakdown
for 7 nights
$5,787 SGD for 7 nights
Home in Islesboro
Charming New England Summer Barn - on an island
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
1.5 bathrooms
1.5 bathrooms
22–27 Aug
22–27 Aug
$3,174 SGD
$2,856 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 15 reviews
5.0 (15)
Top guest favourite
Guest favourite
Home in Northport
Double On The Rocks, ocean view family retreat
7 bedrooms
7 bedrooms
,
·
9 beds
9 beds
,
·
4 bathrooms
4 bathrooms
22–27 Oct
22–27 Oct
$4,199 SGD
Show price breakdown
for 5 nights
$4,199 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 18 reviews
5.0 (18)
1
2
3
4
…
15
