The Best Vacation Rentals to Book in Hilton Head Island, South Carolina

Sea Pines Plantation oozes sultry South Carolina ambiance, particularly at dusk
Sea Pines Plantation oozes sultry South Carolina ambiance, particularly at dusk
Photo of Nick Dauk
20 December 2021
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Island time has a whole different meaning on Hilton Head Island. Just a stone’s throw from the Georgia border, this part of the South Carolina Lowcountry blends coastal vibes with mainland convenience. Golf, beach-bumming, and sweet tea-sipping are all on the agenda no matter the time of the year. Stay for a spell in these vacation rentals and places to stay in Hilton Head Island – bookable on Culture Trip – and get acquainted with the charming island vibes that you’ll only find in the South.

Duck Hawk 27 – for setting a standard

Duck Hawk 27 exterior in split level construction with terrace featuring furniture and manicured gardens
Courtesy of Duck Hawk 27 / Expedia
Fair warning: the breathtaking ocean views and the grand architectural detail of this Hilton Head Island vacation rental will forever set the standard for your holiday getaways. A Brazilian hardwood balcony just outside of the chef’s kitchen will make every meal feel like you’re at an exclusive resort. The boardwalk leading from your backyard to the beach feels like a gateway to bliss. The yard itself is stunning in its own right, with a sand volleyball court, fire pit, pool, hot tub and sun deck.

Forest Drive 13 – for adults and kids alike

Forest Drive 13 exterior with steps leading to front door and a large driveway and garage
Courtesy of Forest Drive 13 / Expedia
Get away on a family vacay in the Lowcountry at this five-bedroom, four-bathroom holiday home. The beach and golf are within reach, so feel free to get an early start on the day. Don’t worry about the kids – when the teens stir from their slumber around noon, they’ll be perfectly content playing pool and watching movies in the entertainment room. When you return, you’re welcome to mix a cocktail at the wet bar and turn up the volume on the theater system.

Links 10B – for going out, or staying in

Links 10B exterior in light grey color with a large garage and a manicured lawn with small bushes
Courtesy of Links 10B / Expedia
Beaches are only a short ride away from this cute three-bedroom holiday home. You could walk, but we think you’ll want to have a speedy way to return to the Carolina room of this spacious villa. It’s the perfect spot to pour a drink and dive into a good book after spending all day in the sun. The fact that this Hilton Head vacation rental comes with a four-person golf cart only sweetens the deal, though bike paths around the island are also accessible just outside the front door.

Ocean One 103 – for catching the rays

Ocean One 103 lounge with flatscreen tv, floral armchairs and a light grey color scheme
Courtesy of Ocean One 103 / Expedia
Oceanfront and close enough to the beach to warrant wearing your swimsuit around the clock, this three-bedroom, three-bathroom condo is exactly where a sunseeker wants to spend their holiday. Grab your favorite sun worshippers and give everyone a healthy dose of vitamin sea as you tan between the sand and the pool. When the moon comes out, Coligny Plaza is where you’ll find beachy drinks to give you an island buzz all night long.

St Andrews 1780 – for golfers

St Andrews 1780 elegant lounge area with flatscreen tv, plush white sofa and outdoor deck
Courtesy of St Andrews 1780/ Expedia
It may not be the famous St Andrews in Scotland, but great golf is still within reach at this second-floor, two-bedroom vacation home in Hilton Head Island. Sit under cathedral ceilings and consider where you’ll play the first round during your vacation. We suggest one of the three courses at Palmetto Dunes Resort – it’s right next door so you’ll have the walk to get limbered up. Return home after every round to a wraparound porch and cold Arnold Palmer that pair together for a perfect 19th hole.

Cottages 11 – for a pet-friendly vacay

A cozy cottage near the beach, plus pet-friendly perks, means spending all day on the palm-covered porch of this two-two villa – complete with pet wash area. It’s situated in the mid-island, which means you won’t have to leave the pups alone for long when you run out for a doggie-free dinner. Of course, you can always cook up your own cuisine in between cuddle sessions. Fix a plate of grub, fill a bowl of water and spend the evening rocking on the porch with your furry companions.

Haul Away 33 – for sun lounging

Haul Away 33 pool surrounded by loungers and trees with steps leading to the main building
Courtesy of Haul Away 33 / Expedia
If you can’t make the 11-minute walk to the beach from this four-bedroom home, fret not. There are still plenty of ways to soak up the sun from this Hilton Head vacation rental. The private pool under the Spanish moss would be our first choice, because the sun loungers are already primed. The terrace is also a contender, particularly because it’s right outside of the master bedroom, which means rolling out of the sheets and into the sun.

Baynard Park 6 – for a spooky stay

Baynard Park 6 exterior with lawns, trees and indoor pool visible through glass conservatory
Courtesy of Baynard Park 6 / Expedia
Call the Sea Pines Resort your holiday home. A private screened pool, patio and sprawling backyard will keep you outside of this three-bedroom vacation rental for hours at a time. Surrounded by the Harbour Town Golf Links and Stoney Baynard Ruins, you have a great chance of spotting shooting stars from the pool deck – and maybe a spirit or two if any wander over from the rumored haunted plantation grounds nearby. Thank goodness you’re allowed to bring along two dogs during your stay.

Full Sweep 62 – for a working vacation

Full Sweep 62 exterior with patio doors leading to outdoor pool
Courtesy of Full Sweep 62 / Expedia
Who needs ocean views when you can spend your holiday poolside gazing at the Robert Trent Jones Golf Course? This three-bedroom vacation rental near Hilton Head’s prized greens is chic, stylish and ready to please the whole family. An office space beside the dining room is perfect for last-minute work or homework sessions in between trips to Pirate’s Island Adventure Golf. The kids will have plenty of space for playing in the backyard.

Coligny Villas 43 – for a home-from-home

Coligny Villas 43 outdoor pool surrounded by loungers and trees with seating area beneath umbrellas in the sun
Courtesy of Coligny Villas 43 / Expedia
A half-mile walk from Coligny Beach Park, this two-bedroom Hilton Head vacation rental is a townhome that feels like your home. A galley kitchen and dining table set for four share the downstairs with the living room while the bedrooms hang out upstairs. Pull back the sliding glass doors to find outdoor seating, and more importantly, the pool area. Walk to the beach if you prefer or chill by the pool – either way, do so with an iced latte from Watusi Cafe next door.

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