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Hilton Head, SC 5+ Bedroom Vacation Rentals

Filter 5+ Bedroom Hilton Head Properties by: Company | Oceanfront | Pet-Friendly | or choose different a Area or Bedrooms
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87 rentals found
5 Bedroom Near Ocean Home

Tucked away just four rows from the ocean and directly across from a beach access path, this roomy 5 bedroom, 4 bathroom home offers the ideal blend of comfort, privacy, and unbeatable location.As you enter, you’re greeted by an open floor plan...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Spacious Modern Getaway with Private Poo...

Summary:Full Sweep 66The Space:This handsome, modern home showcases high-end finishes throughout and is appealingly located just a 10-min. walk from the pristine beaches of Hilton Head Island. “Full Sweep” offers the ideal blend of comfort...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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
Private Oceanfront Home with Private Poo...

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

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Fall Winter Escape: Value for Golf/Tenni...

This striking, 5 bedroom, 4.5 bathroom three story home is located in the most delightful area of Harbour Town. It sits between the Lighthouse and the 16th green of Harbour Town Links Golf Course, just off the 18th fairway and Calibogue Sound, in...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Amazing Oceanfront estate

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 interiors feature...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Spacious Villa waterview haven with deck...

Summary:Sound Villas 1452The Space:A roomy haven in the Sound Villas community, this family friendly home is a sure bet for a vacation no matter the time of year! The sprawling three story floor plan features ample room to relax and entertain both...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
60 Lawton Rd: Sea Pines

Welcome to the 5BR/4BA BESTNEST at 60 Lawton Road. Charmingly refreshed 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
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 fantastic for appreciating wildlife and nature! With broad vistas from every window of the marsh and Braddock Cove, you're...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
Enjoy panoramic lagoon views and private...

This striking 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
Large Home with Spectacular Panoramic Vi...

You're going to appreciate this sizable home with spectacular expansive vistas of Robert Trent Jones Golf Course and the 11 Mile Lagoon! From when you first pull up to the home you'll notice it's very private with a modest fenced-in garden in the...

  • Hilton Head
  • 6 Bedrooms
  • 5 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 marvelous...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Stunning oceanfront home with pool, priv...

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...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Gorgeous oceanfront beach home with priv...

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 huge flat screen TV's and calming sitting areas to appreciate the...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 21
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
Close to Beach, Pool, Elevator, Game Roo...

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...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 21
Beautiful home on the 11-mile lagoon sys...

Come savor this enormous 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 delightfully decorated throughout with wood floor and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
3 Shore Crest, Chefs Kitchen, Free Golf,...

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...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18