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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
Secluded Sea Pines retreat with private ...

Summary:Royal RetreatThe Space:Escape to this luxury estate boasting two separate poolside structures and ample seating areas inside and out - ideal for entertaining. The roomy and handsome property is under new ownership and has been thoughtfully...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 20
North Forest Beach home with a private p...

Summary:Holloman Trace 23 Flip Flop PhilosophyThe Space:This newly constructed, North Forest Beach ocean home is ready to host all of your favorite people! Located in North Forest Beach, this home features all of the luxuries you crave; a private...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
Luxury 6-Bedroom Family Retreat | Heated...

Welcome to 99 Sandcastle Court, a extravagant 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...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
Large Golf Course View Home with Large P...

This delightful 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 charming sunroom along with a enchanting...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Spacious Home with Private Pool, Game Ro...

Summary:Grandiose TimesThe Space:Book your next family reunion or group vacation at Grand Times, a five-bedroom home with a private pool and terrific location near the beach and multiple golf courses.This home has consistently received 5-star...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Beautiful home on the 11-mile lagoon sys...

Come appreciate 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 elegantly decorated throughout with wood floor and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Unbeatable views from private pool with ...

Summary:Wren Drive 18The Space:Appreciate waking up to the sights and sounds of this lush island in the Lowcountry. This home is marvelous for appreciating wildlife and nature! With broad vistas from every window of the marsh and Braddock Cove...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
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 impressive 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
13 Moonshell, Close to Beach, Pool, Big ...

13 Moonshell Rd, Hilton Head is a ideal getaway for a coastal escape. With its five bedrooms and three bathrooms, it offers ample space for guests to relax and relax. The cavernous fenced backyard with a private pool and outdoor bar provides a...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Large Six Bedroom Custom-Built Home with...

This home is designed to fit your next family vacation! The kitchen comes completely equipped to meet your family's cooking needs with stainless steel appliances and bespoke cabinetry, including two ovens and microwave. The enormous kitchen island...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Elegant 5 Bedroom House

Step inside this delightfully appointed five-bedroom home, where roomy interiors, thoughtful coastal details, and exceptional outdoor living come together to create the ideal setting for a Hilton Head Island hideaway.As you enter the home, you are...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
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
1 Shore Crest, Large Pool, Ping Pong, Be...

1 Shore Crest Lane, Hilton Head Island is a elegant home constructed in 2022 and offers 5 bedrooms & 5 bathrooms, a huge pool and a calming outdoor entertainment space. This enchanting beach home is just a fast 3-5 min. walk to the Burkes Beach, is...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
Spacious house by the beach with screene...

Summary:Salt Air SanctuaryThe Space:Just a fast walk down the street to Driessen Beach Park, this beautiful home in Hilton Head, SC, offers the ideal location for a beach hideaway. Walk through the natural environment on the way to the sandy beach...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
New Pool! minutes to Hilton Heads best b...

This beautiful 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