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Search results; 293 homes in Smith Island

Top guest favourite

Cottage in Smith Island

Levering Creek Cottage with private dock

2 bedrooms, 2 beds, 1 private bathroom

8–13 Aug

$1,218 SGD for 5 nights

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4.97 out of 5 average rating, 261 reviews

Top guest favourite

Home in Smith Island

Island Time (whole house rental)

5 bedrooms, 9 beds, 5.5 bathrooms

24–29 Aug

$4,278 SGD for 5 nights

4.96 out of 5 average rating, 69 reviews

Top guest favourite

Home in TYLERTON

3 bedroom/2.5 bath Smith Island bungalow with dock

3 bedrooms, 4 beds, 2.5 bathrooms

18–23 Jul

$1,249 SGD for 5 nights

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 147 reviews

Home in Smith Island

Pelican Cove *Pet Friendly*Golf Cart*Boat Slip

2 bedrooms, 3 beds, 1 bathroom

18–23 Jul

$1,357 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Smith Island

Come enjoy Summer on Smith Island at the HH Ranch

1 bedroom, 2 beds, 1 bathroom

25–30 Jul

$1,762 SGD for 5 nights

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Free cancellation

4.96 out of 5 average rating, 23 reviews

Guest favourite

Cottage in Smith Island

Pet-Friendly Smith Island Cottage w/ Golf Cart!

2 bedrooms, 3 beds, 1 bathroom

17–22 Aug

4.97 out of 5 average rating, 37 reviews

Home in Smith Island

The Pirates House Lands End

1 bedroom, 2 queen beds, 1 bathroom

18–23 Jul

$1,371 SGD for 5 nights

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Free cancellation

Guest favourite

Cottage in Smith Island

IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental

3 bedrooms, 4 beds, 1.5 bathrooms

25–30 Jul

$1,470 SGD for 5 nights

5.0 out of 5 average rating, 64 reviews

Home in Smith Island

Shady's Bayside Retreat

3 bedrooms, 5 beds, 1.5 bathrooms

21–26 Jul

$1,494 SGD for 5 nights

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Free cancellation

Top guest favourite

Home in Smith Island

Discover Smith Island! (But breakfast first)

2 bedrooms, 3 beds, 1 bathroom

28 Jul – 2 Aug

$1,200 SGD for 5 nights

5.0 out of 5 average rating, 30 reviews

Guest favourite

Home in Smith Island

Smith Island Spectacular Sunsets!

4 bedrooms, 7 beds, 2 bathrooms

19–24 Jul

$1,256 SGD for 5 nights

4.83 out of 5 average rating, 86 reviews

Top guest favourite

Cabin in Tangier

Beach Road Oasis, Tangier Island, VA

3 bedrooms, 4 beds, 1 bathroom

19–24 Jul

$1,218 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 39 reviews

Top guest favourite

Home in Tangier

Island Oasis, Tangier Island, Virginia

3 bedrooms, 3 beds, 1 bathroom

30 Aug – 4 Sept

$1,409 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 156 reviews

Top guest favourite

Home in Tangier

Hope Haven Cottage

2 bedrooms, 5 beds, 1 bathroom

19–24 Jul

$1,263 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 62 reviews

Home in Westover

Waterfront Cottage on Goose Creek Westover, MD

3 bedrooms, 4 beds, 2 bathrooms

3–8 Aug

$2,069 SGD for 5 nights

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Free cancellation

Guest favourite

Home in Reedville

Summer Breeze waterfront new home-Private Beach

3 bedrooms, 4 beds, 2 bathrooms

23–28 Aug

$2,010 SGD for 5 nights

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Free cancellation

4.94 out of 5 average rating, 81 reviews

Guest favourite

Home in Crisfield

BayTime

3 bedrooms, 7 beds, 2 bathrooms

27 Jul – 1 Aug

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Free cancellation

4.79 out of 5 average rating, 150 reviews

Top guest favourite

Home in Tangier

Watermans Hideaway, Tangier Island, Chesapeake Bay

3 bedrooms, 5 beds, 1 bathroom

30 Aug – 4 Sept

$1,369 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 183 reviews

Top guest favourite

Home in Crisfield

Marshall’s Retreat Chesapeake small town getaway

3 bedrooms, 5 beds, 2 bathrooms

20–25 Jul

$1,446 SGD for 5 nights

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Free cancellation

4.99 out of 5 average rating, 102 reviews