Hilton Head, SC 5+ Bedroom Vacation Rentals

Summary:Whistling Swan 3The Space:You don't have to compromise any sense of home at this striking 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...

**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 huge 16' x 32' pool, and features an outdoor fire pit ideal for a nighttime hosting around the pool...

Close to fishing, the sea, and more, this smoke-complimentary vacation home brings it all within reach. Your feet will make short work of the 5-min. walk to Adventure Cove or the 13-min. walk to Burkes Beach. This 5-bedroom, 3-bathroom rental...

Summary:Crabline Court 31The Space:Find the ideal group hideaway at this family-friendly beach home, located just a half-mile from the beach. You’ll adore the palm-studded backyard, highlighted by a covered private pool. Fire up the gas grille for...

Summary:Summer HouseThe Space:With a fireplace, a pool, cavernous common areas, and plenty of beds to lay your head down at nighttime, this bright home is the ideal place for your next hideaway. If you’re looking for a family-friendly hideaway...

You're going to be happy you chose this sizable home with plenty of room for your family to spread out! The kitchen is very nice with dark wood cabinets, stainless steel appliances, granite countertops and bar seating for five. Adjacent to the...

Summary:Surf ScoterThe Space:Surf Scoter offers luxury vacation rental at its best! This impressive multi-level home, located just four homes from the beach, has been refreshed throughout with an abundance of bespoke features. With over 5,000 square...

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 fantastic location...

Summary:Dune Lane 105The Space:If you’ve been planning a group hideaway to Hilton Head but haven’t yet found the ideal place, stop scrolling - here it is. With an unbeatable oceanfront location just two miles from Coligny Beach Park, beach...

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 gorgeous, nine-bedroom Beachcomber home sports a private pool and spa and provides broad living spaces, as well as marvelous vistas of the beach and the...

Welcome to this roomy and versatile 5-bedroom vacation home, thoughtfully designed for families and groups looking to relax and reconnect. With generous living spaces and a welcoming ambiance, it's the ideal home base for your next hideaway.Inside...

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...

**Luxurious 6-Bedroom Beach Home Just Steps from North Forest Beach!**Escape to your dream vacation in this cavernous and handsomely designed 6-bedroom, 6 full and 2 half bath beach home, just a few sandy steps from the striking North Forest Beach...

Welcome to 99 Sandcastle Court, a extravagant 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...

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. Appreciate high-end finishes, a chef's kitchen, sunroom, covered deck...

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 gorgeous professionally decorated coastal beach home. As a guest at Serenity Now you...

This home is designed to fit your next family vacation! The kitchen comes entirely equipped to meet your family's cooking needs with stainless steel appliances and bespoke cabinetry, including two ovens and microwave. The enormous kitchen island has...