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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
6 Terra Bella, Oceanfront, Elevator, Pri...

6 Terra Bella Trace, Hilton Head Island is located between the salt marsh and the Atlantic Ocean, 6 Terra Bella Trace is a beach lover's heaven. This impressive property features 6 bedrooms and 8 bathrooms. The chef's kitchen features...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Unbeatable views from private pool with ...

Summary:Wren Drive 18The Space:Savor waking up to the sights and sounds of this lush island in the Lowcountry. This home is amazing for appreciating wildlife and nature! With broad vistas from every window of the marsh and Braddock Cove, you're sure...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
16 Singleton Shores, OceanViews, Pool, E...

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...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
12 Haul Away - 5 Bedroom - Private Pool,...

This amazing near ocean home in the heart of Palmetto Dunes is brand new to the rental market for summer 2024! With only a 5 min. walk to the beach, private pool, private dock, and a fantastic layout for families, this is sure to be a new favorite...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Spacious family-friendly home with priva...

Summary:High Water 9The Space:Set within the esteemed Palmetto Dunes community, High Water 9 is an broad single-level luxury home designed for comfort, space, and effortless coastal living. Featuring seven handsomely furnished bedrooms, this private...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 22
Pet and Friendly Shipyard Home with 5 Be...

3 Port Au Prince is a amazing 5 bedroom, 3.5 bath, pet friendly home located in the gated community of Shipyard Plantation. The entirely equipped kitchen has granite countertops, new range, island that seats 3, and breakfast table for six. Just...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Beautiful home on the 11-mile lagoon sys...

Come savor this sizable five bedroom and five bathroom home located on Palmetto Dunes' 11-mile lagoon system! Located within the heart of Palmetto Dunes Oceanfront Resort, this home has been gorgeously decorated throughout with wood floor and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Sunny & bright home near the beach with ...

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...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Dog friendly home with private pool, WiF...

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 appreciate the palm-studded backyard, highlighted by a covered private pool. Fire up the gas...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Enjoy panoramic lagoon views and private...

This gorgeous pet friendly home is thoughtfully designed with both comfort and style in mind. With an upsized porch overlooking the lagoon, sunny pool, and the ideal great room, this home is sure to impress.Upon entry you are greeted by an enormous...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Sandcastle by the Sea - 3 blocks to beac...

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 spectacular...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Large Golf Course View Home with Large P...

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

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Wonderful golf and lagoon views- Pet Fri...

VIEWS VIEW VIEWS! LOCATION! LOCATION! LOCATION!This near ocean home in Palmetto Dunes has it all, offering both privacy and simple access to the impressive coastline! As you enter the 2-story living room the huge windows fill the room with natural...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Amazing Oceanfront estate

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...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Secluded Sea Pines retreat with private ...

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 beautiful property is under new ownership and has been...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 20
Large Sprawling Home Very Close to the B...

This huge six bedroom and seven bathroom home has everything you'll need to provide a ideal vacation for your whole family! All furnishings in the entire home has been replaced and there are too many updates to name!The sprawling chef-style kitchen...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 12
2nd Row Palmetto Dunes home with private...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Step inside to an impressive, upsized entryway that immediately sets the tone for this exceptional home. The huge entrance features a sweeping spiral staircase...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Bright & Expansive Beach Retreat with Pr...

Summary:Cartgate 21The Space:Freshly Updated, Cavernous 6-Bedroom Retreat with Private Pool Near the BeachWelcome to your ideal Lowcountry escape—this elegantly refreshed, broad home offers six bedrooms and five bathrooms, comfortably...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16