We’re fond of a beach getaway in any season, of course, but there’s something particularly alluring about renting a beach house in the winter. Hilton Head Island is one of the best year-round American beach destinations. And there’s no better way to experience the beach, and the outdoor offerings of the island, than by posting up for a week at one of the over-the-top luxurious Hilton Head Island rentals. You can opt to rent a private residence on a beach the locals favor, like Burkes or Coligny Beach, or browse properties in resort communities, like Sea Pines Resort and Palmetto Dunes Oceanfront Resort. Either way, Hilton Head Island rentals abound for those who want to stay right on the water or nestled on a championship golf course with a private pool. Here, 12 luxury rentals (yes, every rental has a private pool) on Hilton Head Island.
Key to the Sea on Dune Lane
This oceanfront, 5,000-square-foot property, nestled on the scenic North Forest Beach has four stories, seven bedrooms, and can host up to 26 people. There’s a room for the kids to bunk on the fourth floor, three master bedrooms with views of the ocean, and indoor and outdoor fireplaces. Adding to the over-the-top offerings of this home, each of the upper three floors have expansive decks. They all face the Atlantic Ocean, as does the luxe, lounge chair-surrounded pool and spa on the ground floor. Rent for five nights minimum, from $1,234 per night.
Best Nest on Green Wing Teal
Within Sea Pines Resort, right on the beach, is a five-bedroom Hilton Head Island rental with floor-to-ceiling windows gazing out to the water. With a gorgeous deck and polished wood paneling heightening the luxurious interiors, plantation shutters, and an indoor fireplace, the opulence is felt in every corner of this house. And it wouldn’t be complete without multiple patios, a heatable pool and spa, and a well-groomed yard. Rent for four nights minimum, from $1,934 per night.
Oceanfront House on Duck Hawk
Also in the luxe Sea Pines Resort, a wooded boardwalk-style path leads up to this two-story house. It sleeps 14 and boasts ocean views from most rooms of the house, not to mention a pool, hot tub, and multiple living areas and game rooms. And outside, you’ll find a volleyball court in the yard, and an inviting sundeck—it really does feel like having a mini-resort all to yourself. Rent for three nights minimum, from $1,578.
Cozy Three-Bedroom in Palmetto Dunes
If you’re after a chic island home but aren’t in need of an expansive, multistory home, opt for this 3,000-square-foot Hilton Head Island rental in Palmetto Dunes Oceanfront Resort. Rather than vacationing beachside, this is a classic South Carolina golf course rental. While the beach is about 10 minutes (walking), the golf course is right at the property’s edge and sits on the resort’s lagoon. The four-bedroom on Palmetto Dunes’ George Fazio Golf Course has a private pool and spa, a fireplace in the living room, and a private dock leading out to the lagoon. Rent from $300 per night.
Second Row Home on Grey Widgeon
A minute walk to the beach, this two-story, five-bedroom house is modern and airy, with floor-to-ceiling windows and multiple decks. Surrounded by lush greenery—and yet still steps from the beach—the house also has a private pool and spa. While the design is tasteful, with marble countertops and hardwood floors, it’s family-friendly, with a kids’ bunk bed room. To top it off, there’s an indoor fireplace and an outdoor fire pit. Rent for three nights minimum from $937 per night.
11 Armada in Palmetto Dunes
A home within Palmetto Dunes Oceanfront Resort, striking even from afar with beautifully designed floor-to-ceiling windows on both levels, this six-bedroom is outfitted with over-the-top amenities like a wet bar and a Peloton bike. Each of the six rooms has an ensuite, and outside, there’s a pool, spa, and grill for days spent swimming, mixing drinks, and enjoying the gorgeous weather. But the best part of this house—better than the view from the tall bay windows—is the walking path that takes you right to the ocean in just a few steps. Price on request.
3 Full Sweep in Palmetto Dunes
This “coastal contemporary” four-bedroom rental is perfect for a family retreat to Hilton Head Island, with an enormous pool and the perks of living right in the heart of Palmetto Dunes. The beach is a 15-minute walk, if you can tear yourself from the vacation home’s sprawling deck. Price on request.
Luxury Eight-Bedroom in Palmetto Dunes
From the glittering pool to the floor-to-ceiling windows on both floors of this Southern-style beach mansion, the details of this rental are superfluous. The Palmetto Dunes home sleeps 18, with eight bedrooms, a pool (and an outdoor pool table, to boot), and gorgeous sundecks. The opulent retreat is just a few blocks from the beach, golf course, tennis courts, and abounding other recreational activities. Rent for seven nights minimum from $1,153 per night.
Richard’s Second Row Beach House
Steps from Burkes Beach, this light yellow colonial-esque mansion has a beautiful front porch and interior wood paneling, both of which give it an air of Southern extravagance. With three bedrooms, the master suite on the top floor has a charming private deck and a marble jacuzzi tub in the ensuite. Primed for a week filled with outdoor (and indoor) activities, the house is equipped with kayaks and stand-up paddleboards—and a ping pong table. Rent from $350 per night.
Five Bedrooms on North Forest Beach
Three stories, five bedrooms, eight beds, 12 people, two decks, one pool, and one spa. That’s what you’ll find at this Airbnb retreat. The design was inspired by Coastal Living, and the perks are all in the details, from the ensuite bathroom attached to every bedroom, to the waterfall hot tub. It’s just a short walk from the shores of North Forest Beach, but you’ll have ocean views from both decks. Rent from $763 per night.
Oceanfront Five-Bedroom Sea Pines Home
The view of the sun setting over the ocean from your private wooded walkway and porch is what you’re paying for at this rental. Though, to be clear, the enormous pool and spa, lavish marble bathrooms, and five bedrooms certainly add to the value as well. You’ll love the Sea Pines Resort location, the deck looking out toward the water, and the option to walk right down to South Forest Beach in the mornings. Rent for a minimum of four nights from $933 per night.
Three Bedrooms in Palmetto Dunes
With gorgeous views of the George Fazio golf course in Palmetto Dunes, this three-bedroom is perfect for a couple or a small family keen on a rental with a private pool. A small but pristine pool and hot tub is built into this home, and there’s a lovely deck from which you can sip your coffee in the morning—and your cocktails in the evening (or, hey, anytime) while gazing out at the lush Hilton Head Island scenery. And, of course, the beach is just around the corner—a 10-minute walk from the house. Rent from $391 per night.