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Hilton Head, SC 5+ Bedroom Vacation Rentals

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97 rentals found
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
Large Golf Course View Home with Large P...

This pretty 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 charming sunroom along with a enchanting nook...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Pet and Friendly Shipyard Home with 5 Be...

3 Port Au Prince is a outstanding 5 bedroom, 3.5 bath, pet friendly home located in the gated community of Shipyard Plantation. The entirely equipped kitchen has granite countertops, new range, island that seats 3, and breakfast table for six...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
205 Jacana-\

**Luxurious 6-Bedroom Beach Home Just Steps from North Forest Beach!**Escape to your dream vacation in this roomy and elegantly designed 6-bedroom, 6.5-bath beach home, just a few sandy steps from the impressive North Forest Beach. Whether you're...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
3 Shore Crest, Chefs Kitchen, Free Golf,...

3 Shore Crest Lane, Hilton Head Island. Luxury awaits in this bespoke-constructed 5-bedroom home in Burkes Beach, just a 5-min. walk to the beach and adjacent to Chaplin Park. Savor high-end finishes, a chef's kitchen, sunroom, covered deck, pool...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
44 Mooring Buoy- 3rd Row (176 yard walk)...

You can practically feel the sand between your toes! This Palmetto Dunes island beauty is at the end of the beach path, so you’re just a few flip-flops or barefoot steps to the ocean and fun in the sun. The first-floor living area has a elegant...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Sprawling coastal home with private pool...

Bradley Beach Road EstateOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Offering a memorable, family-friendly, coastal escape, this impressive home is...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Beautiful & Spacious House Near Beach w/...

Cartgate 21Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Freshly updated, roomy home with six bedrooms and five baths that accommodates up to 16 people...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Stunning Oceanfront Hideaway with Privat...

HeavenOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please read our important pool heat information to help you have the best vacation possible!*This...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Unbeatable views from private pool with ...

Wren Drive 18Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Appreciate waking up to the sights and sounds of this lush island in the Lowcountry. This home is...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
Gorgeous oceanfront beach home with priv...

Amazing oceanfront home…..your ideal vacation hideaway! This home is ideal for entertaining with eight bedrooms, eight full baths, 1 half bath and huge living areas with sizable flat screen TV's and calming sitting areas to appreciate the...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 21
Fall Winter Escape: Value for Golf/Tenni...

This gorgeous, 5 bedroom, 4.5 bathroom three story home is located in the most splendid 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
Beautiful Oceanfront Home with Large Pri...

This huge six bedroom seven bathroom oceanfront home has everything you've ever wanted in a vacation! As you enter the home you're greeted by a cavernous ceiling with enormous modern chandelier. On your left is the formal dining room, which...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Wonderful golf and lagoon views

VIEWS VIEW VIEWS! LOCATION! LOCATION! LOCATION!This near ocean home in Palmetto Dunes has it all, offering both privacy and simple access to the handsome coastline! As you enter the 2-story living room the sizable windows fill the room with natural...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
14 Collier Beach, Oceanfront, Pool, Elev...

14 Collier Beach, Hilton Head Island is a striking oceanfront estate that offers a state-of-the-art chef's kitchen, an open-concept living and dining area leading to an oceanfront pool, deck, and grille. The home features a extravagant master suite...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
Luxurious home with private pool, centra...

Surf ScoterOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Surf Scoter offers luxury vacation rental at its best! This impressive multi-level home, located...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Close to beach, pickleball, tennis & gol...

Flagg 2-Serene RetreatOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You’ve found gold with this beautiful, family-friendly home, with a serene yet...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
10 Iron Clad- Luxury Ocean Front Home, 6...

Welcome to 10 Iron Clad, a impressive 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 savor their beach vacation. A one million dollar remodel...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 17