Hilton Head Island

Coastal South Carolina, twelve miles of Atlantic beach, and oak-shaded plantation communities.

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4923 waterfront rentals·10 shores·Every listing on the water·Updated 2026-10-15

Hilton Head's foot-shaped barrier island sits just across the Georgia line. Gated plantation communities (Sea Pines, Palmetto Dunes, Shipyard) house most luxury rentals. Golf is everywhere, the beach is firm enough to bike, and October is the sweet spot for weather plus price.

StateSC
Peak seasonJune to August
Best forWaterfront stays
Featured125 rentals
The curated list · 125 rentals

Where we would stay in Hilton Head Island.

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Sleeps Shore More

Pages Rentals with Pool321Oceanfront Rentals201Beachfront Rentals116Soundfront and Bayfront Rentals8Waterfront Rentals325Waterfront Houses125Waterfront Condos198Rentals for Couples and Small Groups235Rentals That Sleep 8 or More94Rentals That Sleep 12 or More37Large Group Rentals23Big Rentals with a Pool92Waterfront Rentals Under $300 a Night229Waterfront Rentals Under $500 a Night274Luxury Rentals35
Beachfront escape with pools, hot tub, WiFi, washer dryer, & central AC
No. 121

Beachfront escape with pools, hot tub, WiFi, washer dryer, & central AC

Villa
2 bedroom sleeps 8 private pool

Island Club 2103 Escape to the beach at this beautifully situated ground-floor, oceanfront condo in the peaceful, 27-acre Island Club on Hilton Head Island. Perfect for a relaxing coastal getaway, this charming retreat offers the ideal blend of comfort, convenience, and resort-style amenities. Step outside to your private furnished patio, where you can enjoy the fresh ocean breeze, listen to the waves, and soak up the beautiful South Carolina sunshine. Inside, you’ll find a bright and welcoming living space designed for relaxation. The well-equipped full kitchen has everything you need to prepare anything from your morning coffee to delicious home-cooked meals after a day at the beach.

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51 Ocean Club
No. 122

51 Ocean Club

Villa
2 bedroom sleeps 6 private pool

Oceanfront Villa in S.Forest Beach. 2BD/2BA/Hosts 6 Proudly hosted this oceanfront villa in the heart of South Forest Beach offers the ultimate beachfront getaway with unbeatable convenience and coastal charm. Located on the main floor, this beautifully appointed 2-bedroom, 2-bath villa accommodates up to 6 guests and allows you to park right outside your door, unload with ease, and enjoy the comfort of single-level living throughout your stay. Designed with inviting nautical and coastal-inspired décor, the villa immediately sets the tone for a relaxing beach vacation the moment you step inside.

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Dont Worry, Beach Happy 1BR Oceanview King Bed Villa in HHBT Resort
No. 123

Dont Worry, Beach Happy 1BR Oceanview King Bed Villa in HHBT Resort

Villa
1 bedroom sleeps 4 private pool

HH Beach & Tennis 233C Wake up to breathtaking, unobstructed ocean views in this coastal chic villa at the ever popular Hilton Head Beach & Tennis Resort. Perfect for couples or small families, this newly listed retreat is literally steps to the beach. Start your mornings with coffee on the private balcony as the sun rises over the Atlantic, and unwind in the evenings with a brand new 55” Smart TV, high speed WiFi, and central AC comfort. Step inside to a well equipped kitchen with stainless steel appliances and granite countertops, refresh in a full bathroom with a tub/shower combo, and stretch out in a plush king bed and sleeper sofa.

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309 Breakers
No. 124

309 Breakers

Villa
1 bedroom sleeps 6

Ocean Views. Walk to Everything! 1BD/1BA/Hosts 5. Free Bikes! Proudly hosted this beautifully remodeled oceanfront villa in the heart of North Forest Beach offers breathtaking Atlantic views, modern coastal style, and an unbeatable walk-everywhere location. Situated in an end-unit at the popular Breakers community, this inviting retreat accommodates up to 5 guests and is the perfect home base for couples, small families, or friends looking to experience the very best of Hilton Head Island. Inside, the bright, open-concept living space is designed to maximize the spectacular ocean views.

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231 Breakers
No. 125

231 Breakers

Villa
1 bedroom sleeps 5 private pool

Oceanfront Dream Villa in North Forest Beach! Free Bikes and Close to Everything! Proudly hosted this bright and inviting oceanfront villa offers the perfect blend of comfort, convenience, and coastal charm in the heart of North Forest Beach. With beautiful natural light and a relaxed beachy feel throughout, this one-bedroom retreat is designed to make your island getaway effortless from the moment you arrive. The thoughtfully arranged layout includes a comfortable bedroom with a queen bed, a sleeper sofa in the living room, and a cozy twin bed tucked into the hall area, perfect for small families or groups.

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Search every stay in Hilton Head Island on Booking.com

Hotels, beach houses, apartments, and resorts. Free cancellation on most rooms. Then add a flight in or a rental car for dune drives.

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Curated luxury alternative

Prefer a boutique hotel or villa?

If a hand-picked, design-led hotel sounds better than a vacation rental, Skylark Travel Group covers the same destinations with curated boutique stays, Mr & Mrs Smith, exclusive deals, real human concierge.

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Before you book, read these
Booking Direct vs. Vrbo vs. Airbnb: Which One Wins for Beach Rentals
The platform you book on changes the price, the cancellation policy, and who picks up the phone when something goes wrong.
Booking Direct vs. Vrbo vs. Airbnb: Which One Wins for Beach Rentals
The platform you book on changes the price, the cancellation policy, and who picks up the phone when something goes wrong.
Booking Direct vs. Vrbo vs. Airbnb: Which One Wins for Beach Rentals
The platform you book on changes the price, the cancellation policy, and who picks up the phone when something goes wrong.
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