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Hilton Head, SC 5+ Bedroom Vacation Rentals

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98 rentals found
Lovely house with gourmet kitchen, scree...

Black SkimmerOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This property in the Sea Pines development sits among the natural beauty of Hilton Head Island's...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
Oceanfront, Sea Pines, Pool & Private Be...

This oceanfront beach home is for a marvelous family (or multi-family) holiday. The property is huge and is one of the most private on the beach. It combines an original but refreshed beach "bungalow" with an extension that adds a master bedroom...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Private home in Hilton Head Island with ...

Located within the esteemed Palmetto Dunes Oceanfront Resort on Hilton Head Island, this elegantly upgraded 5-bedroom, 3-bathroom home sits on a charming corner lot and offers the ideal blend of comfort, luxury, and coastal appeal.Step inside to an...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Dreamy island oasis with private pool, g...

Gunnery 10 Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Step into your island getaway and make the best memories with friends and family in no time here at...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Sea Pines Home w/ Private Pool, Family-F...

North Sea Pines Drive 44Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please read our important pool heat information to help you have the best vacation...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
8 Bedroom/8.5 Bathroom Large Luxurious H...

This cavernous 4th row Palmetto Dunes home is the ideal place for a sizable family hideaway or golf trip! The beach path is directly across from the home and the multiple indoor and outdoor living spaces, this home makes for an ideal getaway for any...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 26
Wonderful golf and lagoon views

VIEWS VIEW VIEWS! LOCATION! LOCATION! LOCATION!This near ocean home in Palmetto Dunes has it all, offering both privacy and simple access to the beautiful coastline! As you enter the 2-story living room the huge windows fill the room with natural...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Oceanfront home with huge windows and a ...

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

  • Hilton Head
  • 9 Bedrooms
  • 10 Bathrooms
  • Sleeps 28
Secluded home & pool house with private ...

Whistling Swan 3Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You don't have to compromise any sense of home at this striking island getaway. Surrounded by...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Conveniently located, gorgeous home with...

Curlew 8Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Curlew 8 is a opulent second-row private home featuring ocean vistas and chic, coastal décor. This...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 28
Family-Friendly Home w/Private Pool, Scr...

Gloucester 36Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Gloucester 36 offers everything you would want for your Hilton Head vacation: a great location...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Secluded Sea Pines retreat with private ...

Royal RetreatOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to this luxury estate boasting two separate poolside structures and ample seating areas...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 20
3rd row Luxury rental - Low Min nights  ...

* Extensive Open floor plan for generational gatherings* Luxury Furnishings & Linens* Hot Tub / Pool on living level * Luxury Soaps, Shampoo's & Lotions * Free Packages for some stays* Welcome Packages upon arrival * 24 hour access to...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Private Oceanfront Home with Private Poo...

You'll appreciate this six bedroom oceanfront home located in esteemed Palmetto Dunes Oceanfront Resort. Boasting numerous sizable windows facing the oceanfront, this home provides oceanfront vistas from nearly every room! As you enter, you are...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
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 savor the...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Beautiful ocean view house w/ private po...

Hidden in HiltonOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel beach living luxury at its best in this striking home located just 2 rows from the beach...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Stunning oceanfront home offering privat...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This impressive 5-bedroom, 5.5-bathroom home is located in the heart of North Forest Beach. Ideally located, it features direct access to the pristine sandy...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
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