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Search results; Over 1,000 homes in Shelter Island

Top guest favourite

Guest house in Shelter Island

Bayfront 1BR/2BR detached guesthouse with pool

1 bedroom, 2 beds, 1 private bathroom

1–6 Aug

$3,158 SGD for 5 nights

,

4.99 out of 5 average rating, 74 reviews

Top guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$10,020 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 40 reviews

Top guest favourite

Place to stay in Shelter Island

Casual Island Getaway - Walk to the Beach

1 bedroom, 1 queen bed, 1 bathroom

4–9 Oct

$1,186 SGD for 5 nights

4.92 out of 5 average rating, 142 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

1–6 Aug

$12,937 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds, 2 bathrooms

10–15 Aug

$6,484 SGD for 5 nights

4.93 out of 5 average rating, 84 reviews

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

14–19 Aug

$7,340 SGD for 5 nights

4.91 out of 5 average rating, 94 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

2–7 Aug

$5,433 SGD for 5 nights

4.97 out of 5 average rating, 122 reviews

Home in Shelter Island

Private Shelter Island Escape | Huge Yard + Pool

4 bedrooms, 5 beds, 2.5 bathrooms

9–14 Aug

$10,128 SGD for 5 nights

Guest favourite

Cottage in Shelter Island

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds, 2 bathrooms

10–15 Aug

$7,005 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds, 2 bathrooms

23–30 Aug

$6,093 SGD for 7 nights

5.0 out of 5 average rating, 24 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

3–8 Aug

$5,974 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 13 reviews

Top guest favourite

Room in Shelter Island

Master Suite at RedHouse

1 king bed, 1 bathroom

21–26 Aug

$1,637 SGD for 5 nights

4.95 out of 5 average rating, 166 reviews

Top guest favourite

Home in Shelter Island

Light, spacious 3bdr home steps to Wades Beach

3 bedrooms, 4 beds, 2.5 bathrooms

2–7 Sept

$6,354 SGD for 5 nights

4.93 out of 5 average rating, 44 reviews

Guest favourite

Room in Shelter Island

Magnolia Cape with private entrance & private bath

1 king bed, 1 bathroom

9–14 Aug

$1,703 SGD for 5 nights

4.84 out of 5 average rating, 43 reviews

Guest favourite

Home in Shelter Island

Charming Farmhouse with Pool

6 bedrooms, 3 bathrooms

1–6 Aug

$5,932 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Home in Shelter Island

CASA GYPSEA - a chic and peaceful 3 bedroom house

3 bedrooms, 3 beds, 2 bathrooms

20–27 Sept

$5,192 SGD for 7 nights

5.0 out of 5 average rating, 75 reviews

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds, 1 bathroom

13–18 Sept

$3,531 SGD for 5 nights

4.84 out of 5 average rating, 76 reviews

Guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$6,240 SGD for 5 nights

4.95 out of 5 average rating, 75 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

5–11 Aug

$7,803 SGD for 6 nights

Free cancellation