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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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87 rentals found
2 Collier, Oceanfront, Dogs OK, Pool, Fr...

***Exciting Renovations Underway!***This home is undergoing a impressive, full-home transformation! Renovations include a elegantly redesigned kitchen, refreshed bathrooms, an enhanced pool and pool deck, and the appealing addition of a 6th...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Enjoy panoramic lagoon views and private...

This gorgeous 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 enormous...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Gorgeous oceanfront beach home with priv...

Amazing oceanfront home…..your ideal vacation hideaway! This home is ideal for entertaining with eight bedrooms, eight full baths, 1 half bath and enormous living areas with huge flat screen TV's and calming sitting areas to appreciate the...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 21
Lovely house with gourmet kitchen, scree...

Summary:Black SkimmerThe Space:Appreciate the ultimate Hilton Head Island hideaway in this roomy 5-bedroom, 5-bathroom Lowcountry beach home, charmingly located in the heart of Sea Pines Plantation. Walking paths and boardwalks give you fast and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
5 Bedroom Waterfront Home

Welcome to this roomy 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 hideaway.Inside...

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

You'll be glad you chose this roomy and impressive 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 huge families or groups looking to...

  • Hilton Head
  • 6 Bedrooms
  • 6 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
Sail Away HHI | Private Pool, Walk to Be...

"Sail Away HHI" is a enormous 4500 square foot, 6 bedroom, 6 full bathroom (plus 1 half bath) home located steps away from the beach access. Located in the charming Burkes Beach community of Hilton Head Island, (rated as the best beaches in America...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 19
Expansive Private Oceanfront Home with V...

Fall in appreciate with this broad oceanfront home located on the Atlantic Ocean in striking Palmetto Dunes Oceanfront Resort! As you enter you are welcomed by a sizable staircase and wood floors leading to the kitchen, dining and living areas. ...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
Secluded home & pool house with private ...

Summary:Whistling Swan 3The Space:You don't have to compromise any sense of home at this striking 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
10 Iron Clad- Luxury Ocean Front Home, 6...

Welcome to 10 Iron Clad, a handsome 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
Palatial Home Just a Short Walk to the B...

You'll be glad you and your family chose this enormous five bedroom home with four full baths and two half-baths! The entire home has many upgrades and has been charmingly decorated with comfort and the beach in mind. The kitchen is handsome and...

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

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 interiors feature...

  • Hilton Head
  • 6 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 enchanting and roomy 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
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 handsome home is located in the prime Folly Field Area...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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 adore with this elegant South Forest Beach home! The property is located right outside the Sea Pines ocean gate and is second row to the...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Spacious family home with WiFi, private ...

Summary:Summer HouseThe Space:With a fireplace, a pool, roomy common areas, and plenty of beds to lay your head down at nighttime, this bright home is the ideal place for your next hideaway. If you’re looking for a family-friendly hideaway with...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18