Holiday Rentals in Smith Island
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Holiday Rentals in Smith Island

Historic home on Smith Island w/ dock!

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Spacious 5-bedroom house with WiFi, AC and private deck on charming Smith Island

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK & golf cart rental

Beautiful Bayfront with Sanctuary Private Beach

Private sand beach on Chesapeake Bay--Great for Kids--Sunrise/Sunset Views

Bay Front Small Contemporary

"Gull Cottage" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip included

Private Beach Front Getaway at The Sunshine Beach Cottage.

BEACH COTTAGE BY THE SEA....

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

Newly updated 3 bedroom cottage with Solo Stove fire pit

Lovely 3-bedroom cottage with AC in charming Saxis
Other types of properties in Smith Island you may be interested in

Historic home on Smith Island w/ dock!
Holiday Accommodation Smith Island
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Smith Island are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Smith Island itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Smith Island holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Smith Island, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Smith Island with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.










