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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 amazing property features 6 bedrooms and 8 bathrooms. The chef's kitchen features top-of-the-line...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Newly remodeled home with private pool a...

Feel the ultimate beach hideaway at this newly remodeled 5-bedroom, 4-bathroom home, ideally located just a less than 5 min. walk from the sand. Designed for effortless indoor-outdoor living, this property offers everything you need for a calming...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 9
Elegant 5 Bedroom House

Step inside this gorgeously appointed five-bedroom home, where cavernous interiors, thoughtful coastal details, and exceptional outdoor living come together to create the ideal setting for a Hilton Head Island hideaway.As you enter the home, you are...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
Luxury 2nd Row Home, Chefs Kitchen, Pool...

19 Sand Dollar, Hilton Head Island. Welcome to this striking second-row ocean home blending traditional coastal Carolina styling with high-end details for a memorable beach vacation! Located directly across from a semi private beach, appreciate...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
This home has all the modern comforts to...

4 Cockle Ct. is a Striking Coastal Chic Home just a 5 min. walk to the beach!Upon entering this open concept home you will immediately notice the impressive architectural details of the archways and the high vaulted ceilings. When walking through...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
A beautiful home to help you create your...

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

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Oceanfront home with huge windows and a ...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This elegant, nine-bedroom Beachcomber home sports a private pool and spa and provides broad living spaces, as well as exceptional vistas of the beach and the...

  • Hilton Head
  • 9 Bedrooms
  • 10 Bathrooms
  • Sleeps 22
60 Lawton Rd: Sea Pines

Welcome to the 5BR/4BA BESTNEST at 60 Lawton Road. Gorgeously modernized and filled with natural light, this five-bedroom Sea Pines home offers generous gathering spaces, flexible accommodations, and a private pool overlooking the lagoon. A separate...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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 roomy and enchanting property is under new ownership and has been thoughtfully...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 20
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 handsome coastline! As you enter the 2-story living room the sizable windows fill the room with natural...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Oceanfront, Private Beach Access

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 amazing location, with...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Pet and Friendly Shipyard Home with 5 Be...

3 Port Au Prince is a marvelous 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
12 Whelk, Steps to the Beach, Private Po...

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 freshly remodeled four-story property offers gorgeous...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Two-story home with pool, balcony, deck,...

Summary:Piping Plover 12The Space:Piping Plover 12 is an immaculate and gorgeous 2nd row home located near South Beach in beloved Sea Pines Plantation. Enter this impressive home into the open and inviting entry. You are immediately greeted with the...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 20
16 Singleton Shores, OceanViews, Pool, E...

16 Singleton Shores Manor, Hilton Head Island. Appreciate 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...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14