We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Shelter Island

Cottage in Shelter Island

Cozy, Comfortable Island Cottage

2 bedrooms, 3 beds, 1 bathroom

23–30 Aug

$4,048 SGD for 7 nights

,

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$9,943 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 41 reviews

Top guest favourite

Place to stay in Shelter Island

Casual Island Getaway - Walk to the Beach

1 bedroom, 1 queen bed, 1 bathroom

2–7 Sept

$1,423 SGD for 5 nights

4.92 out of 5 average rating, 143 reviews

Top guest favourite

Guest house in Shelter Island Heights

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds, 1 bathroom

7–12 Sept

$3,059 SGD for 5 nights

4.99 out of 5 average rating, 76 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

6–11 Sept

$4,290 SGD for 5 nights

4.97 out of 5 average rating, 124 reviews

Top guest favourite

Home in Shelter Island Heights

Family Friendly Island Home

4 bedrooms, 5 beds, 2 bathrooms

10–15 Aug

$6,435 SGD for 5 nights

4.93 out of 5 average rating, 85 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

7–12 Aug

$12,535 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds, 2 bathrooms

23–30 Aug

$5,983 SGD for 7 nights

5.0 out of 5 average rating, 24 reviews

Guest favourite

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

9–14 Aug

$5,928 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Top guest favourite

Home in Shelter Island Heights

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

14–19 Aug

$6,695 SGD for 5 nights

4.92 out of 5 average rating, 95 reviews

Guest favourite

Cottage in Shelter Island Heights

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds, 2 bathrooms

10–15 Aug

$6,951 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews

Top guest favourite

Room in Shelter Island Heights

Master Suite at RedHouse

1 king bed, 1 bathroom

21–26 Aug

$1,624 SGD for 5 nights

4.95 out of 5 average rating, 168 reviews

Guest favourite

Cottage in Shelter Island Heights

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds, 1 bathroom

13–18 Sept

$3,504 SGD for 5 nights

4.84 out of 5 average rating, 77 reviews

Top guest favourite

Home in Shelter Island Heights

CASA GYPSEA - a chic and peaceful 3 bedroom house

3 bedrooms, 3 beds, 2 bathrooms

20–27 Sept

$5,152 SGD for 7 nights

5.0 out of 5 average rating, 75 reviews

Top guest favourite

Home in Shelter Island Heights

Private Hay Beach Retreat with Heated Pool

4 bedrooms, 5 beds, 3 bathrooms

5–10 Oct

$6,444 SGD for 5 nights

4.98 out of 5 average rating, 93 reviews

Top guest favourite

Room in Shelter Island

Magnolia Cape with private entrance & private bath

1 king bed, 1 bathroom

9–14 Aug

$1,690 SGD for 5 nights

4.85 out of 5 average rating, 46 reviews

Top guest favourite

Home in Shelter Island

Light, spacious 3bdr home steps to Wades Beach

3 bedrooms, 4 beds, 2.5 bathrooms

8–13 Nov

$3,995 SGD for 5 nights

4.93 out of 5 average rating, 44 reviews

Guest favourite

Home in Shelter Island Heights

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$6,192 SGD for 5 nights

4.95 out of 5 average rating, 75 reviews

Top guest favourite

Home in Shelter Island Heights

Newly Renovated w/ Pool, Hot tub & Fireplace

3 bedrooms, 5 beds, 2 bathrooms

8–13 Sept

$4,448 SGD for 5 nights

4.91 out of 5 average rating, 35 reviews