HiltonHead-SC.com logo

5+ Bedroom Vacation Rentals

Filter 5+ Bedroom Properties by: Area | Company | or choose different Bedrooms
Areas:
No company options available.
Bedrooms:
102 rentals found
Dreamy island oasis with private pool, g...
3.0
(1)

Gunnery 10 Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Step into your island getaway and make the best memories with friends and family in no time here at...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
44 Bradley Beach, Close to Beach, Large ...
4.3
(19)

44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 and has a enormous 16' x 32' pool, and features an outdoor fire pit ideal for a nighttime hosting around the pool or a cool day in the fall! There is plenty of seating...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Spacious Home - Private Pool & Big Deck ...
4.2
(20)

Mooring BuoyOur 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
3rd row Luxury rental - Low Min nights  ...
5.0
(14)

* Grand Open floor plan for generational gatherings* Luxury Furnishings & Linens* Hot Tub / Pool on living level * Luxury Soaps, Shampoo's & Lotions * Free Packages for some stays* Welcome Packages upon arrival * 24 hour access to...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Secluded home & pool house with private ...
3.2
(6)

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 impressive island getaway. Surrounded...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
31 Singleton  Oceanfront, Views, Luxury ...
4.8
(18)

31 Singleton Beach Place in Hilton Head Island, South Carolina epitomizes luxury living at its best. With over 5,500 square feet of living space, this 6-bedroom, 9-bathroom residence offers an unparalleled level of comfort and sophistication. Upon...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
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 gorgeous coastline! As you enter the 2-story living room the huge windows fill the room with natural...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Renovated spacious home with private poo...
4.8
(6)

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
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 awesome vistas of the beach and the...

  • Hilton Head
  • 9 Bedrooms
  • 10 Bathrooms
  • Sleeps 28
44 Mooring Buoy- 3rd Row (176 yard walk)...
4.7
(15)

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
Second row high-end luxury home is mere ...

Located in the charming South Forest Beach area, this freshly constructed (2025) second row high-end luxury home is mere steps from the beach and conveniently located between Coligny Plaza and Sea Pines. The home features six (6) bedrooms, two of...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 23
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
60 Lawton Road, Sea Pines

Welcome to the BESTNEST at 60 Lawton Road in Sea Pines! Here's the skinny - just buzz us for more details: Our advertised prices are our very best rates and calendar shows real time availability. We encourage you to book online!• Delightfully...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Views of both the George Fazio Golf Cour...
5.0
(1)

A very huge and charming home with extremely high vaulted ceilings with vistas of both the award winning George Fazio golf course and Palmetto Dunes' 11 mile lagoon system. Up the front steps you are greeted by a enormous entryway. As you enter...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
Stunning oceanfront home offering privat...
5.0
(6)

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
2 Collier Beach, Oceanfront, Dogs OK, Po...
3.8
(10)

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
Private home in Hilton Head Island with ...

Located within the esteemed Palmetto Dunes Oceanfront Resort on Hilton Head Island, this gorgeously upgraded 5-bedroom, 3-bathroom home sits on a beautiful corner lot and offers the ideal blend of comfort, luxury, and coastal appeal.Step inside to...

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