Hilton Head, SC 5+ Bedroom Vacation Rentals

Summary:Salt Air SanctuaryThe Space:Just a fast walk down the street to Driessen Beach Park, this striking home in Hilton Head, SC, offers the ideal location for a beach hideaway. With its boardwalk winding through a natural environment to the sandy...

You'll adore this six bedroom oceanfront home located in esteemed Palmetto Dunes Oceanfront Resort. Boasting multiple huge windows facing the oceanfront, this home provides oceanfront vistas from nearly every room! As you enter, you are first...

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...

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

True Southern Living at its best! This pretty Sea Pines home with an open floor plan, ideal indoor/outdoor living, tons of natural sunlight, and steps to the world-famed sandy beaches of Hilton Head, this home is a true gem! Coming soon!!!*New...

This property is now under new ownership and the owners are keen to make this already pretty and cavernous home lighter and brighter with a goal of blowing away all guests expectations! 4 Surf Watch Way is a gorgeous 6-bedroom, 5.5-bathroom, pet...

Summary:Collier Court 4The Space:Welcome to your dream hideaway in Hilton Head, SC! Just 50 feet from the beach path, this gorgeous home offers striking vistas of both the ocean and marsh, making it the ideal getaway for families and friends. With 6...

**New Bonus Room Off of the Pool and Updated Bathrooms!!**44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 and has a enormous 16' x 32' pool, and features an outdoor fire pit ideal for a nighttime hosting around the...

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 cavernous and gorgeous property is under new ownership and has been...

Summary:Bradley Beach Road EstateThe Space:Offering a memorable, family-friendly, coastal escape, this pretty home is located in the prime Folly Field Area near all of Hilton Head Island's attractions. Driessen Beach Park is just steps away, and...

Summary:Sandcastle 97The Space:Located in a gated beachside community, Sandcastle by the Sea is a family-friendly 6BR/4BA getaway that promises an elevated vacation experience. This brand-new home features high-end finishes paired with extraordinary...

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

9 Sandy Beach Trail, Hilton Head Island. Welcome to your bespoke-constructed vacation home! This impressive property features an open-concept layout with the kitchen, living, and dining areas facing the pool, creating a seamless indoor-outdoor...

Summary:Whistling Swan 3The Space:You don't have to compromise any sense of home at this gorgeous island getaway. Surrounded by lush foliage with fast access to the beach, you will have no trouble settling in and slipping right into vacation mode...

One of the Finest-Located Homes on Hilton Head Island! Appreciate a true island hideaway at this delightfully 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...

Welcome to Island Impact Vacation Rental at 91 Sandcastle Court, Hilton Head, South Carolina! Constructed in 2020, this home was designed with the goal to make many memories and allow others to do the same while on vacation. This home is located in...

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 newly refreshed four-story property offers gorgeous ocean...

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...