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Search results; 284 homes in Smith Island

Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
2 bedrooms, 2 beds, 1 private bathroom
29 Sept – 4 Oct
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4.97 out of 5 average rating, 263 reviews
Top guest favourite
Home in Smith Island
Island Time (whole house rental)
5 bedrooms, 9 beds, 5.5 bathrooms
24–29 Aug
4.96 out of 5 average rating, 70 reviews
Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Home in Smith Island
Come enjoy Summer on Smith Island at the HH Ranch
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 23 reviews
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
20–25 Aug
5.0 out of 5 average rating, 64 reviews
Home in Smith Island
Pelican Cove *Pet Friendly*Golf Cart*Boat Slip
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.8 out of 5 average rating, 5 reviews
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 queen beds, 1 bathroom
5–10 Aug
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 148 reviews
Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
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
15–20 Aug
4.83 out of 5 average rating, 86 reviews
Top guest favourite
Home in Tangier
Hope Haven Cottage
2 bedrooms, 5 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Cabin in Tangier
Beach Road Oasis, Tangier Island, VA
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 42 reviews
Guest favourite
Cottage in Deal Island
Water View Cottage
2 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
4.93 out of 5 average rating, 168 reviews
Top guest favourite
Home in Crisfield
Cozy Crisfield Cottage
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.92 out of 5 average rating, 63 reviews
Guest favourite
Cottage in Reedville
Private point on the Bay🌤hammock, hot tub, kayaks❤️
3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
4.88 out of 5 average rating, 259 reviews
Cottage in Reedville
The Beach Next Door
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Tangier
Island Oasis, Tangier Island, Virginia
3 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 163 reviews
Guest favourite
Home in Reedville
Inviting you to our Lakeview Cottage Paradise
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
4.76 out of 5 average rating, 17 reviews