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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
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93 rentals found
Oceanfront, Dogs OK, Pool, Free Golf, El...

2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this grand oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own private...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Luxury 6-Bedroom Home with Private Pool,...

Welcome to 99 Sandcastle Court, a extravagant coastal getaway constructed in 2020, located within the exclusive gated community of Sandcastles by the Sea on Hilton Head Island. Perfectly positioned just a short, breezy walk from the pristine sands...

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

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, roomy home with six bedrooms and five baths that accommodates up to 16 people...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Luxury 2nd Row Home, Chefs Kitchen, Pool...

19 Sand Dollar, Hilton Head Island. Welcome to this striking second-row ocean home blending traditional coastal Carolina styling with high-end details for a memorable beach vacation! Located directly across from a semi private beach, savor plenty of...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
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
Stunning oceanfront home with pool, priv...

Dune Lane 105Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you’ve been planning a group hideaway to Hilton Head but haven’t yet found the ideal...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Stunning Oceanfront Hideaway with Privat...

HeavenOur 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 14
Spacious Home with Gourmet Kitchen, Priv...

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
Spacious family home with WiFi, private ...

Summer HouseOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'With a fireplace, a pool, roomy common areas, and plenty of beds to lay your head down at...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Pet and Friendly Shipyard Home with 5 Be...

3 Port Au Prince is a incredible 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
44 Mooring Buoy- 3rd Row (176 yard walk)...

You can practically feel the sand between your toes! This Palmetto Dunes island beauty is at the end of the beach path, so you’re just a few flip-flops or barefoot steps to the ocean and fun in the sun. The first-floor living area has a handsome...

  • Hilton Head
  • 5 Bedrooms
  • 4 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
Beachfront home with private pool, expan...

Dunes HouseOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Appreciate 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
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 gorgeous island getaway. Surrounded by...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
5 Sandy Beach Trail- Beach House w/ Priv...

"Sail Away HHI" is a grandiose 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...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 19
Oceanfront, Elevator, Ping Pong, Private...

10 Collier Beach, Hilton Head Island is an escape to heaven in this gorgeous 6-bedroom, 7-bathroom oceanfront home, offering beautiful ocean vistas and the ultimate in privacy. Unwind by the private pool, savor direct access to the beach, and...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
Close to beach, pickleball, tennis & gol...

Flagg 2-Serene RetreatOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You’ve found gold with this handsome, family-friendly home, with a serene yet...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
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