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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
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 handsome professionally decorated coastal beach home. As a guest at Serenity Now you...

  • Hilton Head
  • 5 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
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
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
Large Oceanfront Home with Private Pool ...

Treat your family with this immense five bedroom home located oceanfront on Catboat Lane within Palmetto Dunes Oceanfront Resort! The gourmet chef's kitchen will be entirely-equipped with everything you'll need to prepare a meal for your entire...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Oceanfront home with huge windows and a ...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This handsome, nine-bedroom Beachcomber home sports a private pool and spa and provides broad living spaces, as well as impressive vistas of the beach and the...

  • Hilton Head
  • 9 Bedrooms
  • 10 Bathrooms
  • Sleeps 22
10 Collier, Oceanfront, Elevator, Ping P...

10 Collier Beach, Hilton Head Island is an escape to heaven in this gorgeous 6-bedroom, 7-bathroom oceanfront home, offering striking ocean vistas and the ultimate in privacy. Unwind by the private pool, appreciate direct access to the beach, and...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
Bright & Expansive Beach Retreat with Pr...

Summary:Cartgate 21The Space:Freshly Updated, Roomy 6-Bedroom Retreat with Private Pool Near the BeachWelcome to your ideal Lowcountry escape—this elegantly refreshed, broad home offers six bedrooms and five bathrooms, comfortably accommodating up...

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

Planning a December Family Getaway?Savor the magic of the season at our attractively decorated beach home in Palmetto Dunes. Take in the festive Christmas lights throughout Palmetto Dunes and all across Hilton Head Island, creating a incredible...

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

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

Welcome to 10 Iron Clad, a charming 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 appreciate their beach vacation. A one million dollar...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 17
Private Oceanfront Home with Private Poo...

You'll appreciate this six bedroom oceanfront home located in esteemed Palmetto Dunes Oceanfront Resort. Boasting multiple 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
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
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
Fall Winter Escape: Value for Golf/Tenni...

This appealing, 5 bedroom, 4.5 bathroom three story home is located in the most gorgeous 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...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
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
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 handsome...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Modern home on 7th fairway with private ...

Summary:Yard Arm 2The Space:Relaxation awaits! Savor staying at this newly-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 Island...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Newly remodeled home with private pool a...

Feel the ultimate beach hideaway at this freshly modernized 5-bedroom, 4-bathroom home, ideally located just a less than 5 min. walk from the sand. Designed for effortless indoor-outdoor living, this property offers everything you need for a calming...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 9