16 Luxurious Hilton Head Vacation Rentals For Your Island Escape

Also located in the gated Palmetto Dunes community, this two-bedroom condo is within walking distance of the beach, golf course, pools, tennis and pickleball center, bike and kayak rental shop, wine bar, and more!

Technically this beach house is located on neighboring Daufuskie Island. No bridge leads to the island, meaning you’ll have to catch a ferry to reach the secluded beachfront property. Looking for less space? Check out this Daufuskie Island cottage.

Part of Hilton Head Island’s prestigious Palmetto Dunes Oceanfront Resort, this five-bedroom, four-and-a-half bathroom retreat can accommodate up to 16 guests. Relax by the pool or in the hot tub. Take advantage of community amenities, including 3 miles of beachfront, three world-class golf courses, a marina, shops and restaurants, and tennis and pickleball courts. The beach is a 4-minute bike ride, 15-minute walk, or a complementary Dunes Buggy ride away. Parking is available for up to six cars, but weekly passes must be purchased.

Overlooking the widest point of the lagoon, this private paradise features a pool and spacious deck. The 5,200-square-foot home also has a billiards room. Watch the sun go down over the water from the dock. Bring a fishing pole to catch and release fish off the lagoon.

Stay on the sandy shore and enjoy gorgeous ocean views at this luxe two-bedroom vacation rental in Harbour Town. Bikes are provided so you can ride to the Harbour Town Lighthouse, which is less than a mile away. Book a tee time at Harbour Town Golf Links, which is just half a mile from here. Up to two dogs are welcome at this pet-friendly place for a fee.

Boasting 180-degree views of the marsh and Calibogue Sound, this lovely vacation home can also be found in the beautiful Sea Pines Resort. Watch the sun go down over the water and keep an eye out for deer and dolphins.

It does not have its own pool, but guests can pay a weekly rate for access to the South Beach Pool, and Sea Pines Beach access is included. Reach the beach easily by bike or via the nearby trolley service. Harbour Town’s shops, restaurants, and big boat marina is just steps away.

Also found in Sea Pines, this private oasis features a screened-in porch and a pool that looks out over the serene tidal marsh. Plus, its less than half a mile from the beach! Beach chairs, beach towels, and pool floats are provided. A communal playground can also be found nearby. Driveway parking is available for up to five cars, but vehicle passes are required.

Nestled in the Sea Pines Plantation neighborhood, this four-bedroom vacation rental boasts lagoon views, a heated pool, and a hot tub. Tennis at the South Beach Racquet Club is included, as is parking for three cars, however, only one vehicle pass is provided.

Situated on a quiet street in a highly sought-after location, this coastal chic ranch home is just a short walk from the beach. There isn’t a pool, but there is a hot tub in the large backyard which is dotted with live oaks and palms. The backyard also offers direct access to the bike/beach path, which you can take to easily reach South Beach Marina, a New England-style marina village located in Sea Pines Resort. South Beach Marina offers boating, fishing, and water sports, and its famous Salty Dog Cafe. Harbor Town and the Sea Pines Beach Club are also an easy bike ride away.

Take advantage of Sea Pines Resort amenities, including 5 miles of pristine beaches and access to the Sea Pines Beach Club, which offers golf and tennis. Hike to Sea Pines Shell Ring, the oldest known archaeological site on Hilton Head Island. Lawton Stables allows visitors to explore the untouched Lowcountry on horseback.

How gorgeous is this oceanfront retreat?! Located in the gated community of Sea Pines, this five-bedroom rental overlooks the Atlantic coastline. Out front, there’s a sofa and fire-pit while out back you can find the heated private pool. There’s even a volleyball net! Car passes are required at $17 per car every week.

Speaking of Sea Pines, this spacious vacation rental features stunning golf course and lagoon views as well as a heated pool and hot tub. Nestled among moss-covered sea oaks and towering palm trees, it lies directly across the street from beach access.

Located in the quiet South Forest Beach community, this spacious vacation home also features a screened-in porch and pool, as well as a hot tub. Coligny Circle’s shops, restaurants, and more are just a short bike ride away, while the beach can be reached in a matter of a couple minutes on foot.

Counting a bunk room for four kids, this five-bedroom vacation rental in North Forest Beach can sleep up to 18 guests. Relax by the pool, in the hot tub, and on the upper-level screened-in porch. Amenities include a Tesla EV charging station, six parking spaces, an elevator, and games like ping pong, bocce ball, and cornhole. Four bicycles are provided to explore the beach or the miles of bicycle trails on the island. Shops and restaurants are conveniently located just one block away. Featuring a pirate ship playground, walking paths, concerts, and a large green space, Lowcountry Celebration Park can be found just a couple of blocks down the road.

If you’re traveling with kids, you’ve got to book the Castle by the Sea! Three of its rooms are kid-themed, with castle-like bunk beds that little ones will love. The garage has been converted into a game room, complete with a pool table, Little Tikes gym, putting green, and a life-size chess set. Even the pool is perfect for kiddos!

Located in the North Forest Beach area of Hilton Head Island, this vacation rental lies less than 90 yards from the beach. The popular Coligny Plaza shopping center is also just an easy walk away.

Featuring an enclosed heated pool and patio that can be used year-round, this spacious vacation rental is just a short stroll from the sandy shore. A ping pong table, mini pool table, and entertainment room are great for the kids. A large kitchen and dining table are perfect for feeding a crowd.

It doesn’t get any nicer than this award-winning oceanfront estate! This 5,700-square-foot “Beach Castle” has been featured on HGTV’s Wow-Worthy Vacation Homes and Design on Hilton Head. Some of the luxurious touches include a heated pool, a private boardwalk to the beach, plenty of decks and outdoor seating areas, an elevator, an electric vehicle charger, a ping pong and foosball table, and a beachside fire table.