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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
Spacious Villa waterview haven with deck...

Summary:Sound Villas 1452The Space:A cavernous haven in the Sound Villas community, this family friendly home is a sure bet for a vacation no matter the time of year! The sprawling three story floor plan features ample room to relax and entertain...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
12 Haul Away - 5 Bedroom - Private Pool,...

This exceptional near ocean home in the heart of Palmetto Dunes is brand new to the rental market for summer 2024! With only a 5 min. walk to the beach, private pool, private dock, and a fantastic layout for families, this is sure to be a new...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Sunny & bright home near the beach with ...

Summary:Sandhill Crane 3The Space:*Please read our important pool heat information to help you have the best vacation possible!*This property has a pool that can be heated between Labor Day and Memorial Day for an additional fee of $95/nighttime. At...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Luxury 2nd Row Home, Chefs Kitchen, Pool...

19 Sand Dollar, Hilton Head Island. Welcome to this beautiful second-row ocean home blending traditional coastal Carolina styling with high-end details for a memorable beach vacation! Located directly across from a semi private beach, appreciate...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
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
10 Collier, Oceanfront, Elevator, Ping P...

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

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
Lovely house with gourmet kitchen, scree...

Summary:Black SkimmerThe Space:This property in the Sea Pines development sits among the natural beauty of Hilton Head Island's palmetto and oak trees. Walking paths and boardwalks give you fast and painless access to the community's beach...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
Sandcastle by the Sea - 3 blocks to beac...

Summary:Sandcastle 97The Space:Located in a gated beachside community, Sandcastle by the Sea is a family-friendly 6BR/4BA getaway that promises an elevated vacation experience. This brand-new home features high-end finishes paired with exceptional...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Stunning oceanfront home offering privat...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This gorgeous 5-bedroom, 5.5-bathroom oceanfront home is located in the heart of North Forest Beach, offering an memorable coastal experience with sweeping...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
1 Shore Crest, Large Pool, Ping Pong, Be...

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

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
Newly remodeled home with private pool a...

Feel the ultimate beach hideaway at this freshly refreshed 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
5 Bedroom Waterfront Home

Welcome to this cavernous and versatile 5-bedroom vacation home, thoughtfully designed for families and groups looking to relax and reconnect. With generous living spaces and a welcoming ambiance, it's the ideal home base for your next...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
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 charming home into the open and inviting entryway. You are immediately greeted with...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 20
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 completely-equipped with everything you'll need to prepare a meal for your entire...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Secluded home & pool house with private ...

Summary:Whistling Swan 3The Space:You don't have to compromise any sense of home at this gorgeous island getaway. Surrounded by lush foliage with fast access to the beach, you will have no trouble settling in and slipping right into vacation mode...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
9 Promontory - Stunning PD Home w/ Golf ...

Welcome to this spectacular, upsized vacation home featuring soaring vaulted ceilings and memorable vistas of the award-winning George Fazio Golf Course and Palmetto Dunes’ breathtaking 11-mile lagoon system. From the huge entry to the broad...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
5 Bedroom 4.5 Bathroom Updated Home

Welcome to your dream vacation home located in the heart of Palmetto Dunes Oceanfront Resort. This gorgeously appointed 5-bedroom, 4.5-bath offers the ideal blend of coastal appeal, modern comfort, and outdoor serenity ideal for creating memorable...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Large Golf Course View Home with Large P...

This handsome home features extravagant wide plank, hand-scraped, black walnut floor throughout the main living areas. This marvelous home consists of six bedrooms, six and a half bathrooms along with an striking sunroom along with a enchanting...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14