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Search results; Over 1,000 homes in Shelter Island

Guest favourite

Home in Shelter Island

Hay Beach Family Home: Fire Pit, Playroom, Yard

3 bedrooms, 4 beds, 2 private bathrooms

19–24 Jul

$5,798 SGD for 5 nights

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4.9 out of 5 average rating, 126 reviews

Guest favourite

Home in Shelter Island

New vacation house on the island with the pool

3 bedrooms, 5 beds, 3 bathrooms

5–10 Jul

$12,817 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Guest favourite

Cottage in Shelter Island

Shelter Island Cottage

5 bedrooms, 6 beds, 1.5 bathrooms

6–11 Sept

$10,376 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 35 reviews

Top guest favourite

Home in Shelter Island

Surf Scoter Cottage Shelter Island

4 bedrooms, 4 beds, 2 bathrooms

23–28 Jul

$7,095 SGD for 5 nights

4.91 out of 5 average rating, 91 reviews

Top guest favourite

Rooms in Shelter Island

Grace House

2 bedrooms, 2 beds, 1 bathroom

12–17 Jul

$2,179 SGD for 5 nights

5.0 out of 5 average rating, 48 reviews

Top guest favourite

Cottage in Shelter Island

3 Bedroom Cottage Gem

3 bedrooms, 4 beds, 2.5 bathrooms

12–17 Jul

$5,592 SGD for 5 nights

4.97 out of 5 average rating, 117 reviews

Guest favourite

Room in Shelter Island

Magnolia Cape with private entrance & private bath

1 king bed, 1 bathroom

5–10 Jul

$1,755 SGD for 5 nights

4.83 out of 5 average rating, 40 reviews

Top guest favourite

Cottage in Shelter Island

Waterfront Getaway on Shelter Island

3 bedrooms, 3 beds, 2 bathrooms

30 Aug – 4 Sept

$7,023 SGD for 5 nights

4.93 out of 5 average rating, 27 reviews

Home in Shelter Island

Captain Don’s Paradise

3 bedrooms, 4 beds, 1.5 bathrooms

1–6 Aug

$5,989 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 12 reviews

Top guest favourite

Place to stay in Shelter Island

Casual Island Getaway - Walk to the Beach

1 bedroom, 1 queen bed, 1 bathroom

1–6 Sept

$1,526 SGD for 5 nights

4.91 out of 5 average rating, 136 reviews

Guest favourite

Home in Shelter Island

Shelter Island Retreat, 5 bdrms near everything!

5 bedrooms, 5 beds, 2 bathrooms

23–30 Aug

$6,654 SGD for 7 nights

5.0 out of 5 average rating, 23 reviews

Top guest favourite

Home in Shelter Island

CASA GYPSEA - a chic and peaceful 3 bedroom house

3 bedrooms, 3 beds, 2 bathrooms

25 Jul – 1 Aug

$9,613 SGD for 7 nights

5.0 out of 5 average rating, 73 reviews

Top guest favourite

Room in Shelter Island

Master Suite at RedHouse

1 king bed, 1 bathroom

5–10 Jul

$1,625 SGD for 5 nights

4.95 out of 5 average rating, 164 reviews

Guest favourite

Cottage in Shelter Island

Large Waterfront Cottage on Historic Estate

3 bedrooms, 4 beds, 1 bathroom

13–18 Sept

$3,540 SGD for 5 nights

4.84 out of 5 average rating, 73 reviews

Home in Shelter Island Heights

Creekside House Shelter Island

4 bedrooms, 5 beds, 3.5 bathrooms

13–20 Jul

Free cancellation

New place to stay

Top guest favourite

Home in Shelter Island

Family Friendly Island Home

4 bedrooms, 5 beds, 2 bathrooms

13–18 Jul

$6,866 SGD for 5 nights

4.93 out of 5 average rating, 83 reviews

Guest favourite

Room in Shelter Island

A room in a sunny cottage with use of pool.

1 king bed, 1 bathroom

27 Jul – 1 Aug

$1,900 SGD for 5 nights

4.95 out of 5 average rating, 146 reviews

Guest favourite

Home in Shelter Island

Shelter Island 4 bed waterfront home with office

4 bedrooms, 5 beds, 2.5 bathrooms

10–15 Jul

5.0 out of 5 average rating, 27 reviews

Guest favourite

Home in Shelter Island

Beautiful beach home with pool & water views!

5 bedrooms, 9 beds, 3.5 bathrooms

4–9 Oct

$6,256 SGD for 5 nights

4.94 out of 5 average rating, 72 reviews