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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
Oceanfront home with huge windows and a ...

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

  • Hilton Head
  • 9 Bedrooms
  • 10 Bathrooms
  • Sleeps 22
Large Second Row Home in the Heart of Pa...

You'll be glad you chose this cavernous and striking second-row home in Hilton Head Island's esteemed Palmetto Dunes Oceanfront Resort! With six bedrooms and six and a half bathrooms, this home is ideal for sizable families or groups looking to...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Spacious family-friendly home with priva...

Summary:High Water 9The Space:Set within the esteemed Palmetto Dunes community, High Water 9 is an broad single-level luxury home designed for comfort, space, and effortless coastal living. Featuring seven charmingly furnished bedrooms, this private...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 22
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
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
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
2 Min Walk 2 Beach. Walk 2 Pickleball Go...

Appreciate handsome Hilton Head Island when the hordes are smaller and the weather is ideal—with daytime temperatures often in the mid-to-high 70s. It’s the ideal time for beach walks, cycling, golf, tennis, pickleball, dining and calming by the...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Amazing Oceanfront estate

NEW TO ISLAND GETAWAY! Set along the shoreline with sweeping Atlantic vistas, this exceptional six-bedroom, 6900 sq foot, oceanfront estate captures the appeal of classic Nantucket style paired with refined coastal luxury. Thoughtfully designed...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
9 Singleton Beach, Ensuites in Every Bed...

9 Singleton Beach, Hilton Head Island. This oceanfront gem is a 10/10 with awe-inspiring vistas! Ideal for multiple families, this impressive seven-bedroom, five-and-a-half-bathroom home spans three stories with an elevator. Professionally...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
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 elegant South Forest Beach home! The property is located right outside the Sea Pines ocean gate and is second row to...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
A beautiful home to help you create your...

This gorgeous near ocean Hilton Head home rental is just a 3-5 min. walk to the beach, has waterway and private pool vistas, striking appointments and a great interior design to help you create a dream vacation.The downstairs features three living...

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

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

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
Two-story home with pool, balcony, deck,...

Summary:Piping Plover 12The Space:Piping Plover 12 is an immaculate and striking 2nd row home located near South Beach in beloved Sea Pines Plantation. Enter this handsome home into the open and inviting entry. You are immediately greeted with the...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 20
Spacious Modern Getaway with Private Poo...

Summary:Full Sweep 66The Space:This handsome, modern home showcases high-end finishes throughout and is appealingly located just a 10-min. walk from the pristine beaches of Hilton Head Island. “Full Sweep” offers the ideal blend of comfort...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
16 Singleton Shores, OceanViews, Pool, E...

16 Singleton Shores Manor, Hilton Head Island. Savor marsh and ocean vistas from every level of this home. Step into the open and bright living area, complete with a wet bar, pool table, and access to your private pool deck. Upstairs, an refreshed...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
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 gorgeous home offers beautiful 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
Elegant 5 Bedroom House

Step inside this attractively appointed five-bedroom home, where cavernous 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...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13