Hilton Head, SC 5+ Bedroom Vacation Rentals

14 Collier Beach, Hilton Head Island is a gorgeous oceanfront estate that offers a state-of-the-art chef's kitchen, an open-concept living and dining area leading to an oceanfront pool, deck, and grille. The home features a opulent master suite with...

You'll be glad you and your family chose this sizable five bedroom home with four full baths and two half-baths! The entire home has many upgrades and has been charmingly decorated with comfort and the beach in mind. The kitchen is striking and...

NEW TO ISLAND GETAWAY! Set along the shoreline with sweeping Atlantic vistas, this exceptional six-bedroom, 6900 sq foot, oceanfront estate captures the appeal of classic Nantucket style paired with refined coastal luxury. Thoughtfully designed...

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...

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...

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! • Attractively...

This elegant home features extravagant wide plank, hand-scraped, black walnut floor throughout the main living areas. This amazing home consists of six bedrooms, six and a half bathrooms along with an charming sunroom along with a enchanting nook...

Welcome to this spectacular, upsized vacation home featuring soaring vaulted ceilings and memorable vistas of the award-winning George Fazio Golf Course and Palmetto Dunes’ spectacular 11-mile lagoon system. From the huge entry to the broad living...

Amazing oceanfront home…..your ideal vacation hideaway! This home is ideal for entertaining with eight bedrooms, eight full baths, 1 half bath and sizable living areas with sizable flat screen TV's and calming sitting areas to appreciate the...

Welcome to our luxury 7BR, 6.5BA coastal escape in North Forest Beach—just 75 steps or 3 mins. down a private path to the sand. Designed for multi-generational gatherings, this home features high-end furnishings, hotel-quality linens, a chef’s...

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...

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

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...

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...

Summary:Surf ScoterThe Space:Surf Scoter offers luxury vacation rental at its best! This striking 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...

Summary:Sea PointeThe Space:This handsome 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...

This lagoon front Hilton Head Island home is located directly across the street from the beach access point and sits on one of the biggest tons in Palmetto Dunes Oceanfront Resort. The back deck is the ideal spot to appreciate the coastal breeze and...

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