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Hilton Head, SC 5+ Bedroom Vacation Rentals

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96 rentals found
Secluded home & pool house with private ...

Whistling Swan 3Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You don't have to compromise any sense of home at this gorgeous island getaway. Surrounded by...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Spacious Home with Private Pool, Game Ro...

Grandiose TimesOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Book your next family reunion or group vacation at Grand Times, a five-bedroom home with a...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
9 Singleton Beach, Newly Renovated, Ocea...

*New Construction Update(Spring 2025): Updated Kitchen, Updated Master Bathrooms, Updated Half Bathroom, (Jack n Jill Bathrooms to be refreshed winter 2025), New Washer and Dryer sets*9 Singleton Beach, Hilton Head Island. This oceanfront gem is a...

  • Hilton Head
  • 7 Bedrooms
  • 5 Bathrooms
  • Sleeps 20
Large Golf Course View Home with Large P...

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

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
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 exceptional vistas make this home one of the most inviting you...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Beautiful ocean view house w/ private po...

Hidden in HiltonOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel beach living luxury at its best in this impressive home located just 2 rows from the...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14