Hilton Head Island

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

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4904 waterfront rentals·19 shores·Every listing on the water·Updated 2026-11-11

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
Featured21 rentals
The curated list · 21 rentals

Where we would stay in Hilton Head Island.

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Expansive Backyard Oasis and Upper Sun Terrace - Exquisite Coastal Retreat
No. 02

Expansive Backyard Oasis and Upper Sun Terrace - Exquisite Coastal Retreat

House
6 bedroom sleeps 14 private pool

Welcome to South Beach Serenity, your luxurious beachfront haven on Hilton Head Island. This stunning retreat invites you to bask in the serenity of sun-soaked days and ocean breezes. Step into the expansive backyard oasis, where a private pool beckons, surrounded by a spacious patio. For those seeking elevated relaxation, ascend to the upper sun terrace, which is equipped with loungers that provide a perfect vantage point for absorbing ocean views. Inside, the main living area is a vision of openness and light, with floor-to-ceiling windows framing the beauty of the sea.

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Private Pool, Outdoor Hot Tub, Gourmet Kitchen - Stunning Retreat
No. 04

Private Pool, Outdoor Hot Tub, Gourmet Kitchen - Stunning Retreat

House
6 bedroom sleeps 12 private pool

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. Outdoor Hot Tub 3. Private Pool (can be heated for an additional fee) 4. Propane tanks for grilling 5. Beverage Refrigerator and Deep Freezer 6. Hair dryers in each bathroom 6. Wifi and smart tv's (streaming only) 8. 6 Backpack Beach Chairs and a beach wagon 9. We offer both a drip coffeemaker and Keurig Oceanfront Sea Pines Luxury.

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

21
curated rentals in Hilton Head Island
On the water
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Oceanfront Access and Stunning Views - Amazing Coastal Escape
No. 16

Oceanfront Access and Stunning Views - Amazing Coastal Escape

House
7 bedroom sleeps 20 private pool

This oceanfront stunner was built in 2019 and offers amazing views as well as direct access to the beach with a private boardwalk. Walk into an amazing great room to unwind from a day out in the sun. The living room has two couches and two comfy chairs that leads out to the first balcony to soak in the picture-perfect view of the ocean. The kitchen is completely stocked with everything you need, and there is plenty of counterspace on the huge kitchen island for many people to cook simultaneously with room to spare. There is seating for 14 at the dining table and 3 stools at the kitchen bar. The main level of the home also contains a powder room and two bedrooms.

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Coastal craftsmanship

Bags made from recycled sails. Handcrafted in Maine.

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Oceanfront Oasis with Private Pool and Spa - Elegant Getaway
No. 17

Oceanfront Oasis with Private Pool and Spa - Elegant Getaway

House
8 bedroom sleeps 20 private pool

welcome to 9 guscio- newly renovated and outlined with elegance in every detail, this 3-story oceanfront home is truly perfect for your next hilton head island family getaway. this home has an extremely open floor plan that allows an easy flow between the living room, kitchen, and dining area. the living room is well-appointed and spacious, and natural light fills every corner in the room through the large windows. there is plenty comfortable seating for everyone to enjoy, and a large flatscreen tv for your entertainment. in the kitchen, there is plenty of walkway and counterspace to allow multiple people to cook simultaneously without feeling crowded.

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Private Pool and Glorious Ocean Views - Exquisite Beachfront Haven
No. 18

Private Pool and Glorious Ocean Views - Exquisite Beachfront Haven

House
8 bedroom sleeps 21 private pool

With a private pool, eight bedrooms, and glorious ocean views, this massive Sea Pines beach house is perfect for group getaways. Welcome to this distinctive vacation property managed locally. The property is situated among the palmettos and oak trees of Hilton Head Island and steps away from the Atlantic Ocean. The lapping of the waves on the beach of this oceanfront home will put you to sleep, while the bedrooms on the street side of the house get a peek at the lagoon across the way. This luxury home is near the southern tip of the island and a short drive from the Salty Dog Cafe and other popular spots.

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In-Ground Pool and Ocean Views - Elegant Beachfront Retreat
No. 19

In-Ground Pool and Ocean Views - Elegant Beachfront Retreat

House
8 bedroom sleeps 26 private pool

Make your next vacation one to remember with this beautiful home in Sea Pines. 23 Black Skimmers modernist style offers the perfect atmosphere for relaxation and entertainment. Welcome to this distinctive vacation property managed locally. This 7,500-square-foot beachfront home features a private, in-ground pool with a spa and a patio overlooking the Atlantic Ocean. With private beach access, this home is perfect for those long beach days! The kitchen is equipped with stainless steel appliances, a split, two-sink granite island set, and ample countertop space, so there's plenty of room to cook delicious meals and easy cleanup with two dishwashers.

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Ocean Access and Private Pool - Stunning Coastal Sanctuary
No. 20

Ocean Access and Private Pool - Stunning Coastal Sanctuary

House
6 bedroom sleeps 18 private pool

this oceanfront home is newly updated and offers direct access to the beach as well as an expansive outdoor entertainment area that is sure to be your favorite spot for summer days! upon entry, you walk into the home's sitting room which has a dining table for 4 and comfortable seating that is perfect to unwind on over your favorite novel. take a few more steps into the massive great room and take in one of the most amazing views on hilton head- the huge windows along with the high ceilings truly help capture an amazing view of the atlantic ocean. there is plenty seating for all around the flatscreen tv on the large sectional and additional chairs if needed.

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Oceanfront Pool and Beach Access - Exquisite Family Retreat
No. 21

Oceanfront Pool and Beach Access - Exquisite Family Retreat

House
8 bedroom sleeps 24 private pool

There is no need to look any further than oceanfront Beachside Bliss for your next family reunion or getaway, as this one-of-a-kind, 8,000-square-foot luxury home will spoil everyone lucky enough to come along. Welcome to this distinctive vacation property managed locally. There is no need to look any further than oceanfront Beachside Bliss for your next family reunion or friends’ getaway, as this one-of-a-kind, 8,000-square-foot luxury home will spoil everyone lucky enough to come along! As soon as the sun comes up, your days will be filled with island fun in the oceanfront pool with a spa and a hot tub. A few feet away, the private beach access will be the cherry on top for beach lovers.

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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

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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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