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Hilton Head, SC 5+ Bedroom Vacation Rentals

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101 rentals found
14 Collier Beach, Oceanfront, Pool, Elev...
4.7
(18)

14 Collier Beach, Hilton Head Island is a impressive oceanfront estate that offers a state-of-the-art chef's kitchen, an open-concept living and dining area leading to an oceanfront pool, deck, and grille. The home features a opulent master suite...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
Beautiful & Spacious House Near Beach w/...
4.8
(4)

Cartgate 21Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Freshly updated, cavernous home with six bedrooms and five baths that accommodates up to 16 people...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
3 Shore Crest, Chefs Kitchen, Free Golf,...
5.0
(2)

3 Shore Crest Lane, Hilton Head Island. Luxury awaits in this bespoke-constructed 5-bedroom home in Burkes Beach, just a 5-min. walk to the beach and adjacent to Chaplin Park. Savor high-end finishes, a chef's kitchen, sunroom, covered deck, pool...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
New to the rental market, 4th row home!

This lagoon front Hilton Head Island home is located directly across the street from the beach access point and sits on one of the biggest tons in Palmetto Dunes Oceanfront Resort. The back deck is the ideal spot to appreciate the coastal breeze and...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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
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
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
11 Dinghy Oceanfront W/ Pool/Spa & Eleva...
4.9
(41)

Don't miss out on this Awesome Oceanfront home with many amenities the island of Hilton Head that has great all year-round weather and known for its sizable, handsome beaches where early morning walks and bicycle rides is the thinks to do to start...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 18
Private Oceanfront Home with Private Poo...

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

  • Hilton Head
  • 6 Bedrooms
  • 6 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
4 Surfwatch Way, Pet Friendly, Large Poo...
4.6
(77)

4 Surf Watch Way is a impressive 6-bedroom, 5.5-bathroom, pet friendly home accommodating up to 16 guests and making it ideal for family get-togethers or enormous gatherings. Outside, a exceptional deck overlooks the pool and spa, with a completely...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Luxury Beach House w/Pool, Elevator & Ga...
5.0
(26)

Sandy Beach Retreat is a opulent 7 bedroom, 6 full bathroom (plus 2 half baths) home located steps away from the beach access. Located in the charming Burkes Beach community of Hilton Head Island, this home has a pretty coastal style design that...

  • Hilton Head
  • 8 Bedrooms
  • 7 Bathrooms
  • Sleeps 22
424 Captains Walk has panoramic ocean vi...
5.0
(2)

This fourth floor penthouse in Captain's Walk is the ideal setting for your next vacation. Upon entering the unit, guests will appreciate expansive vistas from the living room with two sizable couches and a enormous flat screen TV. The dining room...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 11
12 Whelk, Steps to the Beach, Private Po...
4.3
(12)

Welcome to 12 Whelk Street, Hilton Head Island's premier vacation destination, where beachside luxury meets unmatched convenience. Just 145 feet from the pristine sands of Bradley Beach, this newly remodeled four-story property offers gorgeous ocean...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Spacious Beach Getaway with a Private Po...
5.0
(11)

Sensational second row 5 Bedroom home that has been completely remodeled and has a private pool. The floor plan is unique, and offers tremendous flexibility providing both privacy and great common areas that are ideal for two families. Private ...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Modern home on 7th fairway with private ...
4.7
(21)

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! Savor staying at this newly-constructed home overlooking the 7th fairway of the...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Beachfront beauty with pool access - fir...

Sea PointeOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This fashonable five-bedroom home is just steps away from Singleton Beach and the shared community...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
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