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

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

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

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