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
Featured8 rentals
The curated list · 8 rentals

Where we would stay in Hilton Head Island.

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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
135 Mooring Buoy
No. 01

135 Mooring Buoy

House
5 bedroom sleeps 14 private pool

Stunning Pet Friendly Lagoon Front Home with Private Pool and Spa, 4th row from the beach Welcome to this distinctive vacation property managed locally. Welcome to this stunningly renovated fourth row beach home in the heart of Palmetto Dunes, where luxurious indoor living, resort-style outdoor spaces, and breathtaking lagoon views come together on an oversized double lot just moments from the beach. Guests will also enjoy access to Palmetto Dunes amenities, including miles of bike paths, world class golf, tennis, pickleball, dining, and more. As you arrive, the home immediately makes a statement with dual staircases leading up to the grand front entrance.

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Private Marshfront Oasis w/ Pool & Sunset Views
No. 02

Private Marshfront Oasis w/ Pool & Sunset Views

House
4 bedroom sleeps 8 private pool

Welcome to 22 Oyster Landing, a fully remodeled Lowcountry retreat in Sea Pines with sweeping marsh and Calibogue Sound views. Set on over an acre beneath moss-draped oaks, this light-filled home features an open floor plan, white oak floors, and refined coastal style. Enjoy sunsets from the screened porch, patio, or brand-new oversized pool and spa. Four king bedrooms with private baths offer comfort, privacy, and unforgettable Hilton Head living. Welcome to 22 Oyster Landing, a classic Lowcountry home set on a quiet street in Sea Pines Resort with breathtaking views of the marsh and Calibogue Sound.

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5 Hickory Cove
No. 03

5 Hickory Cove

Villa
3 bedroom sleeps 10 private pool

Pet Friendly spacious and modern 3 bedroom villa with stunning lagoon views Welcome to this distinctive vacation property managed locally. This inviting lagoon front villa is ideally located in the heart of Palmetto Dunes, where peaceful water views and effortless beach access come together for a truly relaxing stay. As you enter, you are welcomed into a bright and comfortable living space designed with a relaxed coastal feel. The main living area offers ample seating, creating the perfect place to unwind after a day on the beach or out exploring the island. Large windows bring in natural light and offer tranquil views of the lagoon just beyond.

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Private Pool and Games Room Retreat - Gorgeous Marshside Haven
No. 04

Private Pool and Games Room Retreat - Gorgeous Marshside Haven

House
4 bedroom sleeps 13 private pool

"Come see why vacationers choose Hilton Head Island year after year! This newly built home at ""The Marshes"" on Hilton Head Island features 4 bedrooms and 3 bathrooms. Here at Vacation Rentals we believe in providing you with amenities you won't find anywhere else. The following are included for your comfort, convenience, and enjoyment: 1. Luxury bedding used by the Ritz Carlton/Bath & Beach Towels 2. Free Pool Heat 3. Golf Cart Rental Discount 4. 6 backpack beach chairs and 1 beach wagon 5. Baby Equipment- Pack N Play w/mattress, Highchair, and Umbrella Stroller 6. Ping Pong Table 7. Propane tank for the grill 8. 2nd Refrigerator/Freezer 9. Hair dryers in each bathroom 10.

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Lagoon Front Oasis with Private Dock and Pool - Beautiful Tranquil Escape
No. 05

Lagoon Front Oasis with Private Dock and Pool - Beautiful Tranquil Escape

House
4 bedroom sleeps 12 private pool

"Beautiful 4BR Private Home in Palmetto Dunes Lagoon Front Views with Private Dock and Pool! Welcome to 40 Full Sweep - Palmetto Dunes Resort Your Lagoon-front Oasis Awaits! Escape to the serenity of this beautiful 4-bedroom private home in the exclusive Palmetto Dunes Resort. With panoramic views of the famous 11-mile lagoon, a private dock, and a sparkling pool, this property offers the perfect blend of tranquility and luxury. Just a 15-minute walk to the beach and close to world-class golf, tennis, restaurants, and shopping, this home is ideal for families and groups seeking a premier Hilton Head Island getaway.

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Endless Tides - Marshfront Lands End Retreat. Pool Across Street. 500 Feet to Beach Access
No. 06

Endless Tides - Marshfront Lands End Retreat. Pool Across Street. 500 Feet to Beach Access

Townhouse
4 bedroom sleeps 8 shared pool

"Endless Tides - Marsh Views, Ocean Glimpses, Steps to the Beach & Pool. Hilton Head Island, SC 29928 Welcome to Endless Tides, a beautifully positioned 4-bedroom, 3-bath coastal retreat tucked inside the exclusive gated community of Lands End within Sea Pines. Perfectly situated between Braddock Cove and the Atlantic Ocean, this attached single-family home offers expansive marsh views from nearly every rear-facing room, ocean glimpses from the upper level, the community pool directly across the street, and beach access less than 500 feet away. The location is truly special.

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Lagoon front, 3 story condo w balcony & washer dryer, snowbird-friendly
No. 07

Lagoon front, 3 story condo w balcony & washer dryer, snowbird-friendly

Condo
3 bedroom sleeps 10 private pool

Seascape Villas 3207 Experience the best of Hilton Head Island from this 3 story charming condo just 0.7 miles from Coligny Beach Park. With a prime location near popular attractions like The Boardroom and Harbour Town Golf Links, you'll have endless entertainment options at your fingertips. This condo offers a comfortable retreat with a range of amenities to make your stay enjoyable. Relax by the pool, unwind on the deck or balcony with patio furniture, or head to the beach with easy beach access. Inside, you'll find a well-equipped kitchen with modern appliances, cozy living spaces with TV and cable, and comfortable sleeping arrangements with king, queen, and twin beds.

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Perfectly Located Family Condo with Shared Pool, Central AC, Private Washer and dryer, Free WiFi
No. 08

Perfectly Located Family Condo with Shared Pool, Central AC, Private Washer and dryer, Free WiFi

Condo
2 bedroom sleeps 6 shared pool

Devonshire 207 Devonshire 207 is a beautifully decorated two-bedroom, two-bath, second-floor villa ideally located on the lagoon and golf course in the quaint complex of Devonshire at Port Royal Village. Enjoy the spacious balconies and the lovely Low Country view. This villa has new upgrades and it is a great place to enjoy with your family and friends. Bedroom and Bathroom Configurations: The main bedroom features a wall-mounted flatscreen TV, balcony access, and a private en-suite bath that has a tub/shower combo. The guest bedroom has a wall-mounted flatscreen TV and access to both the covered balcony and the hall bathroom that features a tub/shower combo.

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Browse more in Hilton Head Island

Hundreds more waterfront rentals we haven't featured yet.

Filter by dates, bedrooms, price, and distance to water. These are the full Vrbo and Booking.com inventories for Hilton Head Island.

8
curated rentals in Hilton Head Island
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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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