Hilton Head, SC 4+ Bedroom Vacation Rentals

Summary:Flagg 2-Serene RetreatThe Space:You’ve found gold with this beautiful, family-friendly home, with a serene yet convenient location just mins. from the beach, golf courses, pickleball courts, tennis courts, shopping, and eateries. Slip into...

Summary:Whispering Palms at Tower BeachThe Space:Scenically located on the banks of a relaxing lagoon, this Hilton Head home is the ideal blend of serenity and convenience. Savor a short walk across the street to Tower Beach or walk less than a...

Welcome to 12 Whelk Street, Hilton Head Island's premier vacation destination, where beachside luxury meets unmatched convenience. Just 145 feet from the pristine sands of Bradley Beach, this freshly modernized four-story property offers gorgeous...

Welcome to your dream vacation home located in the heart of Palmetto Dunes Oceanfront Resort. This elegantly appointed 5-bedroom, 4.5-bath offers the ideal blend of coastal appeal, modern comfort, and outdoor serenity ideal for creating memorable...

Located right on the Atlantic in the Sea Pines Plantation, 22 Black Skimmer Rd is frequently praised as a dreamy, family-friendly escape — the kind of place where you make lifelong memories. Guests consistently highlight its marvelous location...

Welcome to this beautiful home, located in the heart of Palmetto Dunes Oceanfront Resort! With two cavernous living rooms and a handsomely modernized Jack-and-Jill bathroom (completely refreshed in 2025 with a sleek tiled walk-in shower and modern...

Located at the end of the street with direct beach path access from the pool, just 2 mins. from the impressive beaches of Palmetto Dunes, this home offers a great space for your next hideaway! Savor countless sunny days by the pool and calming...

Welcome to your dream getaway, where luxury meets leisure in this attractively designed 4-bedroom, 2-bathroom home. Located in a serene neighborhood, this property features an array of amenities, including a private pool, private beach access, a...

Treat your family with this immense five bedroom home located oceanfront on Catboat Lane within Palmetto Dunes Oceanfront Resort! The gourmet chef's kitchen will be completely-equipped with everything you'll need to prepare a meal for your entire...

HILTON HEAD ISLAND. This cavernous 3rd row home is located in the heart of Sea Pines, and is close to South Beach Marina and many island activities. The warm living room features a sectional couch, TV and decorative fireplace and a bathroom off the...

This gorgeous Hilton Head Island vacation rental offers a ideal blend of luxury and comfort for your next hideaway. The roomy living room provides plenty of room to relax and relax, with comfortable seating and a welcoming ambiance for gathering...

Summary:Pelican Road 20The Space:*Please read our important pool heat information to help you have the best vacation possible!*This property has a pool that can be heated between Labor Day and Memorial Day for an additional fee of $69/nighttime. You...

Summary:Grandiose TimesThe Space:Book your next family reunion or group vacation at Grand Times, a five-bedroom home with a private pool and terrific location near the beach and multiple golf courses.Located near the southern end of Hilton Head...

This Hilton Head vacation home offers a comfortable and easygoing setting for your island hideaway. The screened-in porch with a vaulted ceiling is a calming spot to relax, with casual seating overlooking the private backyard pool.Inside, the layout...

Summary:Shipmaster 1805The Space:Shipmaster 1805 is a gorgeously decorated, four-bedroom, three-bathroom townhome only half a mile from the beach. With a first-floor entry, one bedroom on the main level, and three bedrooms upstairs, this home...

Summary:Tupelo Road 28The Space:Savor your very own slice of heaven with this impressive ranch-style getaway. The open layout and broad kitchen allow up to eight guests to comfortably spread out and make this place home. After a delicious meal, kick...

10 Collier Beach, Hilton Head Island is an escape to heaven in this gorgeous 6-bedroom, 7-bathroom oceanfront home, offering handsome ocean vistas and the ultimate in privacy. Unwind by the private pool, savor direct access to the beach, and indulge...

This new, 5 bedroom, 5 ½ bath, home is a ideal fit for extended families, or as a multi-family vacation residence. Feel absolute luxury and convenience in this handsome professionally decorated coastal beach home. As a guest at Serenity Now you...