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Hilton Head, SC 5+ Bedroom Vacation Rentals

Filter 5+ Bedroom Hilton Head Properties by: Company | Oceanfront | Pet-Friendly | or choose different a Area or Bedrooms
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86 rentals found
Large Six Bedroom Custom-Built Home with...

This home is designed to fit your next family vacation! The kitchen comes completely equipped to meet your family's cooking needs with stainless steel appliances and bespoke cabinetry, including two ovens and microwave. The enormous kitchen island...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
12 Haul Away - 5 Bedroom - Private Pool,...

This fantastic 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
Sprawling coastal home with private pool...

Summary:Bradley Beach Road Estate - Sprawling coastal home with private pool, elevator, & spectacular lanai- dog-friendlyThe Space:Offering a memorable, family-friendly, coastal escape, this pretty home is located in the prime Folly Field Area near...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Unbeatable views from private pool with ...

Summary:Wren Drive 18The Space:Savor waking up to the sights and sounds of this lush island in the Lowcountry. This home is fantastic for appreciating wildlife and nature! With broad vistas from every window of the marsh and Braddock Cove, you're...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
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
Enjoy panoramic lagoon views and private...

This impressive pet friendly home is thoughtfully designed with both comfort and style in mind. With an upsized porch overlooking the lagoon, sunny pool, and the ideal great room, this home is sure to impress.Upon entry you are greeted by an...

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

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

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Close to beach, pickleball, tennis & gol...

Summary:Flagg 2-Serene RetreatThe Space:You’ve found gold with this charming, family-friendly home, with a serene yet convenient location just mins. from the beach, golf courses, pickleball courts, tennis courts, shopping, and eateries. Slip into...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
North Forest Beach home with a private p...

Summary:Holloman Trace 23 Flip Flop PhilosophyThe Space:This freshly constructed, North Forest Beach ocean home is ready to host all of your favorite people! Located in North Forest Beach, this home features all of the luxuries you crave; a private...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
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
5 Bedroom Near Ocean Home

Tucked away just four rows from the ocean and directly across from a beach access path, this cavernous 5 bedroom, 4 bathroom home offers the ideal blend of comfort, privacy, and unbeatable location.As you enter, you’re greeted by an open floor...

  • Hilton Head
  • 5 Bedrooms
  • 4 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
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’ spectacular 11-mile lagoon system. From the huge entry to the broad living...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
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
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
Great Hilton Head Location Pet Friendly,...

This property is now under new ownership and the owners are keen to make this already handsome and cavernous home lighter and brighter with a goal of blowing away all guests expectations! 4 Surf Watch Way is a striking 6-bedroom, 5.5-bathroom, pet...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Spectacular home located on the Robert T...

HILTON HEAD ISLAND RENTAL. This spectacular Hilton Head Island home is located on the Robert Trent Jones Golf Course in Palmetto Dunes. Vaulted ceilings, enormous windows, skylights and fantastic vistas make this home one of the most inviting you...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
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 cavernous fenced backyard with a private pool and outdoor bar provides a...

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