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Search results; 290 homes in Smith Island

Guest favourite
Cottage in Smith Island
IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental
3 bedrooms, 4 beds, 1.5 private bathrooms
25–30 Jul
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5.0 out of 5 average rating, 64 reviews
Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
4.97 out of 5 average rating, 37 reviews, 2 bedrooms, 3 beds, 1 bathroom
14–19 Jul
Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
4.97 out of 5 average rating, 259 reviews, 2 bedrooms, 2 beds, 1 bathroom
24–29 Jul
Top guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
4.96 out of 5 average rating, 146 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Jul
Home in Smith Island
Pelican Cove Smith Island *Dog Friendly*Golf Cart*
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 beds, 1 bathroom
10–15 Jul
Guest favourite
Home in Smith Island
Come enjoy Summer on Smith Island at the HH Ranch
4.95 out of 5 average rating, 22 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Jul
Top guest favourite
Home in Smith Island
Island Time (whole house rental)
4.96 out of 5 average rating, 67 reviews, 5 bedrooms, 9 beds, 5.5 bathrooms
24–29 Aug
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
21–26 Jul
Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
5.0 out of 5 average rating, 29 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Jul
Guest favourite
Cottage in Deal Island
Water View Cottage
4.93 out of 5 average rating, 163 reviews, 2 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
Guest favourite
Home in Smith Island
Smith Island Spectacular Sunsets!
4.83 out of 5 average rating, 86 reviews, 4 bedrooms, 7 beds, 2 bathrooms
11–16 Jul
Home in Westover
Waterfront Cottage on Goose Creek Westover, MD
3 bedrooms, 4 beds, 2 bathrooms
10–15 Jul
Top guest favourite
Home in Tangier
Island Oasis, Tangier Island, Virginia
5.0 out of 5 average rating, 154 reviews, 3 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Tangier
Hope Haven Cottage
5.0 out of 5 average rating, 61 reviews, 2 bedrooms, 5 beds, 1 bathroom
19–24 Jul
Guest favourite
Guest suite in Crisfield
The Serenity House
4.78 out of 5 average rating, 269 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
Top guest favourite
Cabin in Tangier
Beach Road Oasis, Tangier Island, VA
4.97 out of 5 average rating, 38 reviews, 3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Reedville
Waterfront FamilyFriendly Home Improved for 2023
4.95 out of 5 average rating, 264 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
3–8 Oct
Top guest favourite
Home in Reedville
Private Waterfront KingBed Dock Firepit Kayak SUP
4.97 out of 5 average rating, 70 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug