HiltonHead-SC.com logo

Hilton Head, SC 5+ Bedroom Vacation Rentals

Filter 5+ Bedroom Hilton Head Properties by: Company | Oceanfront | Pet-Friendly | or choose different a Area or Bedrooms
Areas:
No company options available.
Bedrooms:
96 rentals found
12 Whelk, Steps to the Beach, Private Po...

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 modernized four-story property offers striking...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Second row to the ocean - 5 bedroom newl...

2nd Row Ocean! 5 Bedrooms, 4 Full baths, 2,500sq.ft. Next to Sea Pines Ocean gate.You will definitely fall in adore with this handsome South Forest Beach home! The property is located right outside the Sea Pines ocean gate and is second row to the...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
1 Shore Crest, Large Pool, Ping Pong, Be...

1 Shore Crest Lane, Hilton Head Island is a beautiful home constructed in 2022 and offers 5 bedrooms & 5 bathrooms, a sizable pool and a calming outdoor entertainment space. This striking beach home is just a fast 3-5 min. walk to the Burkes Beach...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
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
Oceanfront home with huge windows and a ...

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

  • Hilton Head
  • 9 Bedrooms
  • 10 Bathrooms
  • Sleeps 28
Sandcastle by the Sea - brand-new, priva...

Sandcastle 97Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in a gated beachside community, Sandcastle by the Sea is a family-friendly 6BR/4BA...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Ocean Views from Patio! Beautifully upda...

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 extravagant second-row private home featuring ocean vistas and chic, coastal décor...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 28
Private Oceanfront Home with Private Poo...

You'll appreciate this six bedroom oceanfront home located in esteemed Palmetto Dunes Oceanfront Resort. Boasting numerous huge 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
5 Bedroom Near Ocean Home

Tucked away just four rows from the ocean and directly across from a beach access path, this roomy 5 bedroom, 4 bathroom home offers the ideal blend of comfort, privacy, and unbeatable location.As you enter, you’re greeted by an open floor plan...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Gorgeous 5 ?? custom home! 5 king suites...

Vacation in luxury in this elegant home! This 4500 square foot home is designed ideally for multiple families. Just a 3-5 min. walk to the beach, this home has everything you could ask for! With 7 bedrooms, 7 and 2 1/2 baths, 3 living rooms and...

  • Hilton Head
  • 7 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Waterfront dream home with pool, lagoon ...

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 10
4 Surfwatch Way, Pet Friendly, Large Poo...

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 huge gatherings. Outside, a marvelous deck overlooks the pool and spa, with a completely fenced...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
5 Sandy Beach Trail- Beach House w/ Priv...

"Sail Away HHI" is a sizable 4500 square foot, 6 bedroom, 6 full bathroom (plus 1 half bath) home located steps away from the beach access. Located in the beautiful Burkes Beach community of Hilton Head Island, (rated as the best beaches in America...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 19
Oceanfront, Private Beach Access

Located right on the Atlantic in the Sea Pines Plantation, 22 Black Skimmer Rd is frequently praised as a dreamy, family-friendly escape — the kind of place where you make lifelong memories. Guests consistently highlight its magnificant location...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
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 generous seating areas...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 20
Ocean and Marsh View Home with private p...

Collier Court 4Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your dream hideaway in Hilton Head, SC! Just 50 feet from the beach path, this...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
10 Iron Clad- Luxury Ocean Front Home, 6...

Welcome to 10 Iron Clad, a charming 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
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