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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
5 Bedroom Waterfront Home

Welcome to this cavernous 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...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
10 Iron Clad- Luxury Ocean Front Home, 6...

Welcome to 10 Iron Clad, a handsome multi-level, ocean front home in the award-winning Palmetto Dunes Resort. With breath taking ocean vistas from nearly every room, your family is sure to appreciate their beach vacation. A one million dollar...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 17
Fall Winter Escape: Value for Golf/Tenni...

This striking, 5 bedroom, 4.5 bathroom three story home is located in the most handsome 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 the...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Great Hilton Head Location Pet Friendly,...

This property is now under new ownership and the owners are keen to make this already striking and cavernous home lighter and brighter with a goal of blowing away all guests expectations! 4 Surf Watch Way is a lavish 6-bedroom, 5.5-bathroom, pet...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
New Pool! minutes to Hilton Heads best b...

This impressive Sea Pines home with an open floor plan, ideal indoor/outdoor living, tons of natural sunlight, and steps to the world-famed sandy beaches of Hilton Head, this home is a true gem! The sun filled living room greets you upon entry. The...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Large Home with Spectacular Panoramic Vi...

You're going to adore this enormous 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 front...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Spacious family home with WiFi, private ...

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...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Close to Beach, Pool, Elevator, Game Roo...

9 Sandy Beach Trail, Hilton Head Island. Welcome to your bespoke-constructed vacation home! This striking 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
Large Six Bedroom Custom-Built Home with...

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...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
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
5 Bedroom Near Ocean Home

Tucked away just four rows from the ocean and directly across from a beach access path, this cavernous 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...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Ocean and Marsh View Home with private p...

Summary:Collier Court 4The Space:Welcome to your dream hideaway in Hilton Head, SC! Just 50 feet from the beach path, this striking home offers beautiful vistas of both the ocean and marsh, making it the ideal getaway for families and friends. With...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
Palatial Home Just a Short Walk to the B...

You'll be glad you and your family chose this huge 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 elegant and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
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 impressive location...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Large Oceanfront Home with Private Pool ...

Treat your family with this immense five bedroom home located oceanfront on Catboat Lane within Palmetto Dunes Oceanfront Resort! The gourmet chef's kitchen will be entirely-equipped with everything you'll need to prepare a meal for your entire...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Sandy Beach Retreat | Pool, Hot Tub, Wal...

Sandy Beach Retreat is a extravagant 7 bedroom (plus a ground level room with Queen pull out couch), 6 full bathroom (plus 2 half baths) home located steps away from Burkes Beach access. Located in the beautiful Burkes Beach community of Hilton...

  • Hilton Head
  • 8 Bedrooms
  • 7 Bathrooms
  • Sleeps 22
8 Bedroom/8.5 Bathroom Large Luxurious H...

This cavernous 4th row Palmetto Dunes home is the ideal place for a sizable family hideaway or golf trip! The beach path is directly across from the home and the multiple indoor and outdoor living spaces, this home makes for an ideal getaway for any...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 26
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