Hilton Head, SC 5+ Bedroom Vacation Rentals

Summary:Sea PointeThe Space:This chic five-bedroom home is just steps away from Singleton Beach and the shared community pool! Bring the whole family and create sun-soaked, lifelong memories in Hilton Head. When your toes aren't dug into the warm...

2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this grand oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own private...

Summary:Sandhill Crane 3The 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 $95/nighttime. At...

Summary:Luna Sea EstateThe Space:This freshly constructed, North Forest Beach ocean home is ready to host all of your favorite people! Located in North Forest Beach, this home features all of the luxuries you crave; a private pool, a hot tub, a...

HILTON HEAD ISLAND RENTAL. This spectacular Hilton Head Island home is located on the Robert Trent Jones Golf Course in Palmetto Dunes. Vaulted ceilings, sizable windows, skylights and exceptional vistas make this home one of the most inviting you...

This cavernous 4th row Palmetto Dunes home is the ideal place for a sizable family hideaway or golf trip! The beach path is directly across from the home and the multiple indoor and outdoor living spaces, this home makes for an ideal getaway for any...

Welcome to the BESTNEST at 60 Lawton Road in Sea Pines! Here's the skinny - just buzz us for more details: Our advertised prices are our very best rates and calendar shows real time availability. We encourage you to book online! • Gorgeously...

One of the Finest-Located Homes on Hilton Head Island! Savor a true island hideaway at this charmingly appointed third-row ocean home in Palmetto Dunes Plantation, just a 2-min. walk to the beach. Unwind in your private heated pool and spa, or walk...

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...

16 Singleton Shores Manor, Hilton Head Island. Savor marsh and ocean vistas from every level of this home. Step into the open and bright living area, complete with a wet bar, pool table, and access to your private pool deck. Upstairs, an refreshed...

Summary:Sound Villas 1452The Space:A roomy haven in the Sound Villas community, this family-friendly home is a sure bet for a vacation no matter the time of year! The sprawling three-story floor plan features ample room to relax and entertain - both...

3 Shore Crest Lane, Hilton Head Island. Luxury awaits in this bespoke-constructed 5-bedroom home in Burkes Beach, just a 5-min. walk to the beach and adjacent to Chaplin Park. Savor high-end finishes, a chef's kitchen, sunroom, covered deck, pool...

Summary:Royal RetreatThe Space:Escape to this luxury estate boasting two separate poolside structures and ample seating areas inside and out - ideal for entertaining. The roomy and elegant property is under new ownership and has been thoughtfully...

31 Singleton Beach Place in Hilton Head Island, South Carolina epitomizes luxury living at its best. With over 5,500 square feet of living space, this 6-bedroom, 9-bathroom residence offers an unparalleled level of comfort and sophistication. Upon...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This striking 5-bedroom, 5.5-bathroom oceanfront home is located in the heart of North Forest Beach, offering an memorable coastal experience with sweeping...

This gorgeous near ocean Hilton Head home rental is just a 3-5 min. walk to the beach, has waterway and private pool vistas, handsome appointments and a great interior design to help you create a dream vacation.The downstairs features three living...

Summary:HeavenThe 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 MUST...

Welcome to 99 Sandcastle Court, a opulent coastal getaway constructed in 2020, located within the exclusive gated community of Sandcastles by the Sea on Hilton Head Island. Perfectly positioned just a short, breezy walk from the pristine sands of...