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Hilton Head, SC 5+ Bedroom Vacation Rentals

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88 rentals found
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 roomy fenced backyard with a private pool and outdoor bar provides a excellent...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Gorgeous new luxury beach house - be the...

This new, 5 bedroom, 5 ½ bath, home is a ideal fit for extended families, or as a multi-family vacation residence. Feel absolute luxury and convenience in this gorgeous professionally decorated coastal beach home. As a guest at Serenity Now you...

  • Hilton Head
  • 5 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
2 Collier, Oceanfront, Dogs OK, Pool, Fr...

2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this elegant oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own...

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

Summary:Bradley Beach Road EstateThe Space:Offering a memorable, family-friendly, coastal escape, this beautiful home is located in the prime Folly Field Area near all of Hilton Head Island's attractions. Driessen Beach Park is just steps away, and...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Modern home on 7th fairway with private ...

Summary:Yard Arm 2The Space:Relaxation awaits! Appreciate staying at this freshly-constructed home overlooking the 7th fairway of the Robert Trent Jones Golf Course, just a short walk or bicycle ride from the sugar sand beaches of Hilton Head...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Luxurious home with private pool, centra...

Summary:Surf ScoterThe Space:Surf Scoter offers luxury vacation rental at its best! This impressive multi-level home, located just four homes from the beach, has been modernized throughout with an abundance of bespoke features. With over 5,000...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
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 striking ocean...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
44 Bradley Beach, Close to Beach, Large ...

**New Bonus Room Off of the Pool and Updated Bathrooms!!**44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 and has a enormous 16' x 32' pool, and features an outdoor fire pit ideal for a nighttime hosting around the...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Luxury 7BR Beach House w/ Pool, Hot Tub ...

Sandy Beach Retreat is a opulent 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 beautiful Burkes Beach community of Hilton Head...

  • Hilton Head
  • 8 Bedrooms
  • 7 Bathrooms
  • Sleeps 22
New to the rental market, 4th row home!

This lagoon front Hilton Head Island home is located directly across the street from the beach access point and sits on one of the biggest tons in Palmetto Dunes Oceanfront Resort. The back deck is the ideal spot to savor the coastal breeze and...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Fall Winter Escape: Value for Golf/Tenni...

This impressive, 5 bedroom, 4.5 bathroom three story home is located in the most pretty 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
3rd row Ocean Luxury - Private Pool/Spa ...

Welcome to our luxury 7BR, 6.5BA coastal escape in North Forest Beach—just 75 steps or 3 mins. down a private path to the sand. Designed for multi-generational gatherings, this home features high-end furnishings, hotel-quality linens, a chef’s...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
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
Wonderful golf and lagoon views- Pet Fri...

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 huge windows fill the room with natural...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
2nd Row Palmetto Dunes home with private...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.Step inside to an impressive, upsized entryway that immediately sets the tone for this exceptional home. The grandiose entrance features a sweeping spiral...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
2 Min Walk 2 Beach. Walk 2 Pickleball Go...

Now is great time to book for September, October and Thanksgiving. Just reduced Fall prices!One of the Finest-Located Homes on Hilton Head Island! Appreciate a true island hideaway at this charmingly appointed third-row ocean home in Palmetto...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
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 exceptional location...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
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 impressive...

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