15 Luxe Hilton Head Rentals That Will Blow Your Mind

If you’re heading to the white sandy beaches of South Carolina on a family vacation, then check out these luxurious Hilton Head Rentals that include vacation home options in Sea Pines and Harbour Town, South Beach, and more.

hilton head rentals
The ocean, a putting green, and a swimming pool set the vibe at this rental

These are perfect luxe vacation home and villa rentals on Hilton Head Island,SC that the rich and famous rush toward (there is even a listing here that was a perfect vacation for a former President and his wife) … but if you bring the extended family or a few family friends, they can be affordable for even us “regular folk.”

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Sea Hawk Lane

Wall-to-wall windows frame ever-changing Atlantic views at this custom-built oceanfront home. It’s set on just one of 10 lots in this exclusive neighborhood, and was designed to make the most of the quiet-but-dramatic setting beside the dunes. Cross the private path to the sand or take the free shuttle to shopping and dining choices.

Details: 16 guests · 6 bedrooms · 10 beds · 8 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Sweet Carolina

Nestled next to the sands at North Forest Beach sits this coastal oasis. Its open floor plan is made for entertaining; the gourmet kitchen, dining room, and spacious living area smoothly flow together. Sky-high windows drench the décor in daylight. From the thatch-roofed palapa, follow a path to the sugary shoreline for a cool ocean dive.

Details: 16 guests · 8 bedrooms · 16 beds · 9.5 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Ocean Jewel

How amazing is this secluded getaway? It’s close to everything downtown and yet still in a quiet rustic mountain setting. It includes a full kitchen and a great patio.

Details: 16 guests · 7 bedrooms · 13 beds · 8.5 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Sandpiper

The spacious interior gives everyone in your group space to spread out, but what’s really magnificent about this home is its backyard where you’ll find stunning views of the shore, plenty of seating, a pool with an overflowing fountain, and a spa. A short walk from the yard leads directly to the beach.

Details: 16 guests · 7 bedrooms · 13 beds · 7.5 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Rum Row

Lagoons lead into the forest and a path leads to the beach at this coastal-chic home on Hilton Head Island. It’s newly built, but evokes centuries of Carolina style with wood floors and coffered ceilings. Part of the Palmetto Dunes Resort, it’s tucked into a quiet, leafy neighborhood less than 1 mile from a sandy Atlantic beach, where you can chase thrills on a surfboard or collect shells.

Details: 12 guests · 5 bedrooms · 5 beds · 4.5 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Oceanfront Oasis

Enjoy the tropical landscape and the first floor elevated balcony ocean views, which span the entire width of this pet-friendly home. Have a day at the private pool or take a break from the sun in a poolside lounge chair underneath the beach umbrella. Stroll along the Folly Field Beach Park boardwalk and witness amazing sunrises or sunsets from this Hilton Head vacation rental. 

Details: 10 guests · 5 bedrooms · 8 beds · 5 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Mooring Buoy

More than 10 miles of still-watered lagoons wind their way past the backyard of this traditionally styled home. Skip the villas and condos at Palmetto Dunes Resort, and instead opt for this quiet, tree-lined neighborhood, with a pool in back and a path to the beach in front. Walk 3 minutes to surf, boogie board, or collect shells on the resort’s broad, sandy Atlantic beach.

Details: 14 guests · 5 bedrooms · 7 beds · 4.5 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Brigantine

Palms shield the ground floor from view while 2nd-story decks look out over the Atlantic at this ocean-view-but-private contemporary villa. In the great room, floor-to-ceiling windows showcase the views; in the bedrooms, clerestory windows provide sunshine and seclusion. Cross the dunes to the beach or walk 14 minutes to the nearest golf course.

Details: 15 guests · 5 bedrooms · 8 beds · 5 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

8 Junket

This oceanfront home offers dramatic views of the Atlantic Ocean. Located in the world famous Palmetto Dunes Plantation, it boasts a panoramic view of the ocean from the upstairs formal living room, dining room, kitchen with attached family room, and eat-in kitchen and sundeck. Guests will also have a magnificent view of the ocean from the downstairs living area, wet bar, and covered patio.

Details: 12 guests · 6 bedrooms · 8 beds · 6 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Sea Oak Lane

Up the beautiful wood and glass staircase is the main living area offering ocean views from the massive wall of windows, the view is breath taking. The living area is warm and inviting, there is plenty of seating, a beautiful fireplace, a large flat screen TV. The well equipped kitchen is open to the living area and large dining area, the chef in the party will be happy.

Details: 14 guests · 6 bedrooms · 7 beds · 6 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Luxury Oceanfront

The open concept house is framed with oversized floor to ceiling windows, designed to capture oceanfront views from all three floors. This iconic home, which has played host to a US President and his wife, underwent a full renovation in 2015 by an award winning builder. The newly designed open concept kitchen was the recipient of the Lighthouse Design Award for the best kitchen renovation.

Details: 15 guests · 5 bedrooms · 8 beds · 5 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Wrap-Around Porch

Get carried away by the stunning surroundings and amenities, including a sparkling private pool and spa, when you come for a beach vacation in this spacious house. Relax on the large wrap-around porch with plenty of seating for dining al fresco, and enjoy a privileged location near the beach where you can make memories with friends and family.

Details: 14 guests · 5 bedrooms · 9 beds · 5.5 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Nantucket Feels

This fantastic 2nd row ocean, is nestled in the palms of the Palmetto Dunes resort. A circular drive leads to a beautiful entrance way and wrap around porch. The grand foyer opens to a huge family room, a fully equipped chef- quality kitchen, and an elegant dining room. 

Details: 12 guests · 6 bedrooms · 6 beds · 7 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

New Beach Home

This recently remodeled majestic beach home is highlighted by its location directly on the beach in Palmetto Dunes and its private backyard w/ heated pool, spa, large patio space, cozy fire pit, covered porch, comfy hammock, and outdoor shower. This Hilton Head Island vacation rental’s back yard is among the coolest!

Details: 12 guests · 4 bedrooms · 6 beds · 5 baths · Rental Info

15 Luxe Hilton Head Rentals That Will Blow Your Mind

Black Duck

Contemporary decor, open floor plan, heated pool with spa and a private path to an uncrowded beach create the perfect venue for your beach vacation with friends and family. There are games, a large wet bar off the pool patio and a wide array of outdoor seating. The unique location at the southern tip of Hilton Head Island offers beautiful sunrises to the east, open ocean views straight ahead, views of Tybee Island in Georgia in the distance, and magnificent sunset views over Dafuskie Island to the west. 

Details: 16 guests · 9 bedrooms · 14 beds · 7.5 baths · Rental Info

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Disclosure: I’m an Airbnb Associate. If you decide to book through the above links, it allows us to earn a small percentage without any additional cost to you. You help two small businesses at once (365AT & the renter), which we greatly appreciate and depend on. Thanks to Airbnb for the photos.