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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
60 Lawton Rd: Sea Pines

Welcome to the 5BR/4BA BESTNEST at 60 Lawton Road. Charmingly remodeled 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
Luxury 6-Bedroom Family Retreat | Heated...

Welcome to 99 Sandcastle Court, a opulent coastal getaway constructed in 2020, located within the exclusive gated community of Sandcastles by the Sea on Hilton Head Island. Perfectly positioned just a short, breezy walk from the pristine sands of...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
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
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
Close to beach, pickleball, tennis & gol...

Summary:Flagg 2-Serene RetreatThe Space:You’ve found gold with this charming, family-friendly home, with a serene yet convenient location just mins. from the beach, golf courses, pickleball courts, tennis courts, shopping, and eateries. Slip into...

  • Hilton Head
  • 5 Bedrooms
  • 5 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 remodeled four-story property offers impressive...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
9 Singleton Beach, Ensuites in Every Bed...

9 Singleton Beach, Hilton Head Island. This oceanfront gem is a 10/10 with awe-inspiring vistas! Ideal for multiple families, this impressive seven-bedroom, five-and-a-half-bathroom home spans three stories with an elevator. Professionally...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
A beautiful home to help you create your...

This gorgeous near ocean Hilton Head home rental is just a 3-5 min. walk to the beach, has waterway and private pool vistas, striking 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
Expansive Private Oceanfront Home with V...

Fall in appreciate with this broad oceanfront home located on the Atlantic Ocean in impressive Palmetto Dunes Oceanfront Resort! As you enter you are welcomed by a grandiose staircase and wood floors leading to the kitchen, dining and living areas...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
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 impressive and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Large Golf Course View Home with Large P...

This charming home features opulent wide plank, hand-scraped, black walnut floor throughout the main living areas. This impressive 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
Oceanfront, Pool, Views, Luxury, Elevato...

31 Singleton Beach Place in Hilton Head Island, South Carolina epitomizes luxury living at its best. With over 5,500 square feet of living space, this 6-bedroom, 9-bathroom residence offers an unparalleled level of comfort and sophistication. Upon...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
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 magnificant vistas make this home one of the most inviting you...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Stunning oceanfront home offering privat...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This impressive 5-bedroom, 5.5-bathroom oceanfront home is located in the heart of North Forest Beach, offering an memorable coastal experience with sweeping...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Secluded home & pool house with private ...

Summary:Whistling Swan 3The Space:You don't have to compromise any sense of home at this delightful island getaway. Surrounded by lush foliage with fast access to the beach, you will have no trouble settling in and slipping right into vacation mode...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12