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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
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 elegant home is located in the prime Folly Field Area near...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Mediterranean Coastal 2nd Row 6 Bedroom ...

Located in the heart of Palmetto Dunes Oceanfront Resort on Hilton Head Island, this handsomely refreshed 6-bedroom, second-row vacation home offers the ideal blend of luxury, space, and an unbeatable location. Just steps from the beach, guests...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 18
Large Home with Spectacular Panoramic Vi...

You're going to appreciate this sizable home with spectacular expansive vistas of Robert Trent Jones Golf Course and the 11 Mile Lagoon! From when you first pull up to the home you'll notice it's very private with a modest fenced-in garden in the...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Large Six Bedroom Custom-Built Home with...

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

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Spacious family home with WiFi, private ...

Summary:Summer HouseThe Space:With a fireplace, a pool, cavernous 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...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
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 huge 16' x 32' pool, and features an outdoor fire pit ideal for a nighttime hosting around the pool...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
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, sizable windows, skylights and amazing vistas make this home one of the most inviting you will...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
New Pool! minutes to Hilton Heads best b...

This pretty Sea Pines home with an open floor plan, ideal indoor/outdoor living, tons of natural sunlight, and steps to the world-famed sandy beaches of Hilton Head, this home is a true gem! The sun filled living room greets you upon entry. The...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
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 delightfully refreshed, broad home offers six bedrooms and five bathrooms, comfortably accommodating...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Secluded Sea Pines retreat with private ...

Summary:Royal RetreatThe Space:Escape to this luxury estate boasting two separate poolside structures and ample seating areas inside and out - ideal for entertaining. The cavernous and handsome property is under new ownership and has been...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 20
Spacious Home with Gourmet Kitchen, Priv...

Summary:Sea Oak Lane 5The 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 $69/nighttime. You...

  • 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, handsome 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
Fall Winter Escape: Value for Golf/Tenni...

This beautiful, 5 bedroom, 4.5 bathroom three story home is located in the most enchanting 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
Large Second Row Home in the Heart of Pa...

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

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
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
Beautiful home on the 11-mile lagoon sys...

Come appreciate this huge five bedroom and five bathroom home located on Palmetto Dunes' 11-mile lagoon system! Located within the heart of Palmetto Dunes Oceanfront Resort, this home has been charmingly decorated throughout with wood floor and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Expansive Private Oceanfront Home with V...

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

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
This home has all the modern comforts to...

4 Cockle Ct. is a Spectacular Coastal Chic Home just a 5 min. walk to the beach!Upon entering this open concept home you will immediately notice the impressive architectural details of the archways and the high vaulted ceilings. When walking through...

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