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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 roomy 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 hideaway.Inside...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
2nd Row Palmetto Dunes 5 Bed/5 Bath Home...

Located at the end of the street with direct beach path access from the pool, just 2 mins. from the gorgeous beaches of Palmetto Dunes, this home offers a great space for your next hideaway! Appreciate countless sunny days by the pool and calming...

  • Hilton Head
  • 5 Bedrooms
  • 5 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
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 handsome and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
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
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 newly refreshed four-story property offers striking ocean...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Second row to the ocean - 5 bedroom newl...

2nd Row Ocean! 5 Bedrooms, 4 Full baths, 2,500sq.ft. Next to Sea Pines Ocean gate.You will definitely fall in appreciate with this enchanting South Forest Beach home! The property is located right outside the Sea Pines ocean gate and is second row...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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
Great Hilton Head Location Pet Friendly,...

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

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

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

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
A beautiful home to help you create your...

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

  • Hilton Head
  • 5 Bedrooms
  • 5 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 marvelous location...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Sail Away HHI | Private Pool, Walk to Be...

"Sail Away HHI" is a enormous 4500 square foot, 6 bedroom, 6 full bathroom (plus 1 half bath) home located steps away from the beach access. Located in the beautiful Burkes Beach community of Hilton Head Island, (rated as the best beaches in...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 19
Spectacular home located on the Robert T...

HILTON HEAD ISLAND RENTAL. This spectacular Hilton Head Island home is located on the Robert Trent Jones Golf Course in Palmetto Dunes. Vaulted ceilings, sizable windows, skylights and marvelous vistas make this home one of the most inviting you...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
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
5 Bedroom 4.5 Bathroom Updated Home

Welcome to your dream vacation home located in the heart of Palmetto Dunes Oceanfront Resort. This charmingly appointed 5-bedroom, 4.5-bath offers the ideal blend of coastal appeal, modern comfort, and outdoor serenity ideal for creating memorable...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
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 charming Burkes Beach community of Hilton Head...

  • Hilton Head
  • 8 Bedrooms
  • 7 Bathrooms
  • Sleeps 22
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