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Hilton Head, SC 5+ Bedroom Vacation Rentals

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96 rentals found
Large Home with Panoramic Views of Rober...

Appreciate sweeping expansive vistas of multiple greens of the Robert Trent Jones Golf Course and a sizable part of the 11 mile lagoon system! See the sunrise over the iconic 10th hole of Robert Trent Jones every morning! There are exceptional...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
This home has all the modern comforts to...

4 Cockle Ct. is a Pretty 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 the...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
Spacious house by the beach with screene...

Salt Air SanctuaryOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Just a fast walk down the street to Driessen Beach Park, this appealing home in Hilton Head...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
3rd row Ocean Luxury - Private Pool/Spa ...

Welcome to our luxury 7BR, 6.5BA coastal escape in North Forest Beach—just 75 steps or 3 mins. down a private path to the sand. Designed for multi-generational gatherings, this home features high-end furnishings, hotel-quality linens, a chef’s...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
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
Renovated spacious home with private poo...

Full Sweep 66Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This property has a pool that can be heated between Labor Day and Memorial Day for an additional...

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

Wren Drive 18Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Savor waking up to the sights and sounds of this lush island in the Lowcountry. This home is...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
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
Amazing Family-Friendly House w/ Private...

High Water 9Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'An broad luxury home in Palmetto Dunes, High Water 9 features a single-level layout with seven...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 22
Dog-friendly home with private pool, WiF...

Crabline Court 31Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find the ideal group hideaway at this family-friendly beach home, located just a half-mile...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
2 Min Walk 2 Beach Pickleball Golf Tenni...

One of the very best located properties in Hilton Head. November and December are great for beach activities: golf, tennis, pickleball. Appreciate our private heated pool and spa.Book Christmas week and week before now while still available. Both...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Modern home on 7th fairway with private ...

Yard Arm 2Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Relaxation awaits! Appreciate staying at this freshly-constructed home overlooking the 7th fairway...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Oceanfront, Sea Pines, Pool & Private Be...

This oceanfront beach home is for a marvelous family (or multi-family) holiday. The property is enormous 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
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 sizable kitchen island has...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Pet and Friendly Shipyard Home with 5 Be...

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

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Large Sprawling Home Very Close to the B...

This huge six bedroom and seven bathroom home has everything you'll need to provide a ideal vacation for your whole family! All furnishings in the entire home has been replaced and there are too many updates to name!The sprawling chef-style kitchen...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 12
Two-story home with pool, balcony, deck,...

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 gorgeous 2nd row home located near South Beach in...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 20