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Hilton Head, SC 5+ Bedroom Vacation Rentals

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101 rentals found
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 painless access to the pretty coastline! As you enter the 2-story living room the sizable windows fill the room with natural...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
10 Iron Clad- Luxury Ocean Front Home, 6...
4.9
(41)

Welcome to 10 Iron Clad, a striking 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 savor their beach vacation. A one million dollar remodel...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 17
Beautiful Oceanfront Home with Large Pri...

This huge six bedroom seven bathroom oceanfront home has everything you've ever wanted in a vacation! As you enter the home you're greeted by a cavernous ceiling with huge modern chandelier. On your left is the formal dining room, which...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Two-story home with pool, balcony, deck,...
5.0
(5)

Piping Plover 12Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Piping Plover 12 is an immaculate and striking 2nd row home located near South Beach in...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 20
16 Singleton Shores, OceanViews, Pool, E...
4.9
(17)

16 Singleton Shores Manor, Hilton Head Island. Savor marsh and ocean vistas from every level of this home. Step into the open and bright living area, complete with a wet bar, pool table, and access to your private pool deck. Upstairs, an refreshed...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Large Private Home with Private Pool and...

You're going to be happy you chose this sizable home with plenty of room for your family to spread out! The kitchen is very nice with dark wood cabinets, stainless steel appliances, granite countertops and bar seating for five. Adjacent to the...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Spacious Home with Gourmet Kitchen, Priv...
4.7
(15)

Sea Oak Lane 5Our 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
5 Bedroom Home w/ Private Pool & 6Seater...
5.0
(5)

Welcome to Island Impact Vacation Rental at 91 Sandcastle Court, Hilton Head, South Carolina! Constructed in 2020, this new single family home was designed with the goal to make many memories and allow others to do the same while on vacation. This...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Fabulous! Huge 5 Bedrm/5 Bath Moss Creek...
4.7
(102)

Moss Creek House Description This 4,500+ sq. ft. home, consisting of 5 bedrooms and 5 baths, that sleeps 12, is located in the handsome Moss Creek private club community. We have an in-ground, plunge pool with lion head water spouts, with the...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Oceanfront home with huge windows and a ...

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

  • Hilton Head
  • 9 Bedrooms
  • 10 Bathrooms
  • Sleeps 28
Spring Escape: Value for Golf/Tennis/Pic...
4.8
(37)

This beautiful, 5 bedroom, 4.5 bathroom three story home is located in the most gorgeous 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
Waterfront dream home with pool, lagoon ...
4.8
(14)

Shell Ring Road 63Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Peace and peaceful await you at this serene hideaway on Hilton Head Island. This home has a...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Family-Friendly Home w/Private Pool, Scr...
4.4
(30)

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
Beachfront home with private pool, expan...
3.8
(14)

Dunes HouseOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Savor life at the beach at Dunes House! This home has impressive vistas of the beach and the...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Bright, newly-remodeled, dog-friendly be...
4.6
(15)

Lookout 1Our 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 possible!*This...

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

This roomy 4th row Palmetto Dunes home is the ideal place for a huge 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
Oceanfront, Sea Pines, Pool & Private Be...
5.0
(65)

This oceanfront beach home is for a awesome family (or multi-family) holiday. It combines an original but refreshed beach "bungalow" with an extension that adds a master bedroom suite, office/study, formal dining room, powder room, elevator, and...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
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 savor the beachfront...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 21