Wow-Worthy Vacation Homes and Design on Hilton Head

Intimate couple retreat or shindig of the century: Whatever your Hilton Head vacation entails, we've got your digs picked out.

By: Carrie Hamblin

Photo By: TruPlace

Photo By: TruPlace

Photo By: Peter Cram Photography

Photo By: Chad Dyar Photography / ©Chad Dyar 2019

Photo By: Jason Adams of Luxury Imaging Company /

Photo By: Bill Lisbon / Imoto Photo

Photo By: Ryan Greco of Moonlight Productions

Photo By: Holger Hopderbeck

Photo By: Flip Harris

Photo By: TruPlace

Home Away From Home

With a huge backyard on a quiet residential street, this beautifully appointed beachside retreat could be your family's Hilton Head home away from home. The gorgeous four-bedroom has all the modern amenities you'd expect, plus dramatic ocean views from nearly every room. After your morning at the beach, kick back in the hammock with a crossword. Or enjoy some quiet time on the private master deck while the kids play in the pool or the backyard. Later, you can plan tomorrow's hike in the Sea Pines Forest Preserve or vote on which movie you'll see at Park Plaza Cinema during family time around the fire pit. BOOK IT: Nightly rates starting at $1,085

Group Golf Getaway

With every amenity to make you and 10 of your closest friends exceptionally comfortable, this five-bedroom modern abode may be the quintessential accommodation for a group golfing trip to Hilton Head. Two living rooms and two gourmet kitchens allow ample space to kick back in and mix your martinis, respectively. But where you'll spend most of your time is lounging in the 1,500-square-foot screened-in outdoor living space. This design achievement is replete with a heated (and jetted) fountain pool with waterfall wall, a hot tub and an outdoor kitchen with grill. Did you get a load of the awesome fire table by the pool? If you do decide to actually leave the property, it's centrally located between some of the island's championship courses, a couple blocks from the beach and minutes from the entertainment of Coligny Plaza. BOOK IT: Nightly rates starting at $815

Besties Couple Retreat

This secluded, two-bedroom cottage on a private island is ready for a two-couple retreat amid the oak trees. Overlooking the Pinckney Island Wildlife Refuge from the Bluffton side, the five-star-rated home is ideal for birdwatchers, fishermen and general appreciators of nature and all her bounty. It's just a 10-minute drive to civilization but that's only when you're ready — and why would you leave? You can watch the sunrise from the dock and set a crab trap for dinner. Kayak around the marsh and go for a swim in the saltwater creek. Watching the sunset from the porch in the evening, the sounds you hear are the low country oysters popping (really snapping shrimp) and your wine glasses clinking as you toast the moment. Wait, is that a night heron? BOOK IT: Nightly rates starting at $335

Serenity in the Sand

Hilton Head's 12 miles of beach play are rivaled only by that of the island's record-breaking 33 golf courses. And this bright and airy Airbnb Plus villa in the Shipyard Plantation is the ideal rental for the couple who want to coordinate their sea time around tee time. The two-bedroom handsomely decorated home resides in the gated "Greens" community, with its private community pool and miles of manicured bike paths. Close to restaurants and shopping, it's a five-minute stroll to the beach and the property overlooks the seventh hole of the championship golf course you'll be tackling later. BOOK IT: Nightly rates starting at $199

Beach Castle

Hilton Head has a wealth of recreation so what better destination for a family get-together? And why scatter around the island when this gorgeous, 5,700-square-foot oceanfront home can hold the entire clan. Perfectly designed to the owners' specifications, you can expect every luxury you would grant yourself if it were your own dream home. Eight bedrooms comfortably accommodate more than 20 people of all ages and requirements (the property has an elevator and two accessible bedrooms and baths). The private boardwalk to the beach is there if you want it, but you can watch the sunrise in your PJs from the beautifully tiled decks and outdoor sitting areas. In the evening, maybe you play with the kids in the pool while the family grillmaster works the outdoor kitchen. At some point you'll have to coordinate who's going horseback riding tomorrow and who's joining the family golf lesson, but the relaxing jets of the spa make it simply impossible to worry about that now. BOOK IT: Weekly rates starting at $10,000

Your Natural Habitat

Instead of renting a home, how about an entire island? Actually, three islands to be exact and they are all yours for exploring. This solar-powered home just south of HGTV Dream Home 2020 is perfect for the couple wanting some relaxation off the grid. The Airbnb Superhost owners pick you up and drop you off in their boat and then it's just you and whatever your hearts desire. Two kayaks beckon for exploration. A couple of fishing poles are waiting for your best casts. The wrap-around porch competes with the backyard firepit for the best space to kick your feet up. Don't worry, you have a few days — you will experience both! But if it's evening, it's time to make your way to the top floor of the lookout tower to relax in the hammock with your someone special and watch the sunset. BOOK IT: Nightly rates starting at $500

Cheery Family Getaway

This cheery little Hilton Head villa is the ultimate vacay spot for a small family. In fact, it's the owners' family getaway, so they take great care in making it ideal for yours — right down to the requisite kid gear, like pack 'n' play, highchair and family-friendly DVDs and games. Its colorful decor and comfortable bedding will brighten your mornings, and the private deck is perfect for grilling burgers in the evening and sipping a glass of wine after the kids nod off. In a small residential development with a community pool and tennis court, it's only a few minutes' walk to the beach. A short bike ride takes you to Coligny Plaza and you're even close to kid-favorite Lawton Stables, with its horses and petting zoo. Your days will be filled! BOOK IT: Nightly rates starting at $155

Island Refuge

The bustle of big-city Hilton Head not quite your speed? This charming domicile in Daufuskie — the tiny island neighbor accessible only by ferry — offers a generous serving of peace and quiet with a side of low country living. The three-bedroom happy home is the perfect size for a couple's getaway and the ideal base to explore the island's Historic District. After the beach and then lunch at popular Lucy Bell's Café, take a nap in the swing bed on the screened-in porch. The cottage is tastefully adorned with local art from island studios you can visit later this afternoon. Once you're sufficiently unwound, the ferry to and from the excitement of Hilton Head runs many times daily. Pet owners rejoice: Clear it with the friendly owner and Fido gets a vacay too. Daufuskie has dog-friendly beaches year-round. BOOK IT: Nightly rates starting at $195

Gals Getaway

This airy three-bedroom cottage with its vaulted ceilings and coastal decor offers a stylish space for a gal-pal Hilton Head beach break. Grab your towel and take the five-minute stroll for a morning swim in the ocean, returning just in time for the lunch made by your late-rising friends. In the afternoon, maybe you dip your toes in the private pool while you enjoy your 5-o'clock-somewhere libations. After your nap, a short bike ride will take you and your friends to nearby Coligny Plaza, with its 60 restaurants, shops and amusements. BOOK IT: Nightly rates starting at $295

Bedecked and Beachfront

Enjoy a private family resort vacation with the luxuries at this extravagant oceanfront home. Eight bedrooms — including an eight-bed bunk room with game loft — accommodate every member of an extended family inside, but on this Hilton Head vacation, everyone is outdoors. Challenge your sister to a game of Ping-Pong while the kids splash around in the lighted pool with bubblers. Yes, it has a gourmet, three-oven kitchen inside, but why not let Grandpa cook dinner at the outdoor grilling bar? It really feels like island living as you relax under the thatched roofs of the covered porch and oceanfront gazebo. If you didn't glimpse the beauty of the Atlantic every morning from one of the plentiful decks and porches, you might forget to walk the few steps down to beach. BOOK IT: Nightly rates starting at $2,345