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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 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 freshly modernized four-story property offers gorgeous...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Secluded home & pool house with private ...

Summary:Whistling Swan 3The Space:You don't have to compromise any sense of home at this gorgeous island getaway. Surrounded by lush foliage with fast access to the beach, you will have no trouble settling in and slipping right into vacation mode...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Close to beach, pickleball, tennis & gol...

Summary:Flagg 2-Serene RetreatThe Space:You’ve found gold with this handsome, family-friendly home, with a serene yet convenient location just mins. from the beach, golf courses, pickleball courts, tennis courts, shopping, and eateries. Slip into...

  • Hilton Head
  • 5 Bedrooms
  • 5 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
New Pool! minutes to Hilton Heads best b...

This pretty Sea Pines home with an open floor plan, ideal indoor/outdoor living, tons of natural sunlight, and steps to the world-famed sandy beaches of Hilton Head, this home is a true gem! The sun filled living room greets you upon entry. The...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Palatial Home Just a Short Walk to the B...

You'll be glad you and your family chose this sizable five bedroom home with four full baths and two half-baths! The entire home has many upgrades and has been gorgeously decorated with comfort and the beach in mind. The kitchen is gorgeous and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Beachfront home with private pool, expan...

Summary:Dunes HouseThe Space:Savor life at the beach at Dunes House! This home has impressive vistas of the beach and the Atlantic Ocean. The open living space on the second floor has living, dining, and a well-equipped kitchen that all look out to...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Large Golf Course View Home with Large P...

This handsome home features extravagant wide plank, hand-scraped, black walnut floor throughout the main living areas. This marvelous home consists of six bedrooms, six and a half bathrooms along with an striking sunroom along with a enchanting...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
9 Singleton Beach, Ensuites in Every Bed...

9 Singleton Beach, Hilton Head Island. This oceanfront gem is a 10/10 with awe-inspiring vistas! Ideal for multiple families, this striking seven-bedroom, five-and-a-half-bathroom home spans three stories with an elevator. Professionally decorated...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
205 Jacana-

**Luxurious 6-Bedroom Beach Home Just Steps from North Forest Beach!**Escape to your dream vacation in this roomy and handsomely designed 6-bedroom, 6 full and 2 half bath beach home, just a few sandy steps from the gorgeous North Forest Beach...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
12 Haul Away - 5 Bedroom - Private Pool,...

This exceptional near ocean home in the heart of Palmetto Dunes is brand new to the rental market for summer 2024! With only a 5 min. walk to the beach, private pool, private dock, and a fantastic layout for families, this is sure to be a new...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Spacious Modern Getaway with Private Poo...

Summary:Full Sweep 66The Space:This impressive, modern home showcases high-end finishes throughout and is charmingly located just a 10-min. walk from the pristine beaches of Hilton Head Island. “Full Sweep” offers the ideal blend of comfort...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Amazing Oceanfront estate

NEW TO ISLAND GETAWAY! Set along the shoreline with sweeping Atlantic vistas, this exceptional six-bedroom, 6900 sq foot, oceanfront estate captures the appeal of classic Nantucket style paired with refined coastal luxury. Thoughtfully designed...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Spacious Home with Private Pool, Game Ro...

Summary:Grandiose TimesThe Space:Book your next family reunion or group vacation at Grand Times, a five-bedroom home with a private pool and terrific location near the beach and multiple golf courses.This home has consistently received 5-star...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
This home has all the modern comforts to...

4 Cockle Ct. is a Spectacular 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...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
6 Terra Bella, Oceanfront, Elevator, Pri...

6 Terra Bella Trace, Hilton Head Island is located between the salt marsh and the Atlantic Ocean, 6 Terra Bella Trace is a beach lover's heaven. This impressive property features 6 bedrooms and 8 bathrooms. The chef's kitchen features...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Two-story home with pool, balcony, deck,...

Summary:Piping Plover 12The Space:Piping Plover 12 is an immaculate and striking 2nd row home located near South Beach in beloved Sea Pines Plantation. Enter this charming home into the open and inviting entryway. You are immediately greeted with...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 20
Spectacular home located on the Robert T...

HILTON HEAD ISLAND RENTAL. This spectacular Hilton Head Island home is located on the Robert Trent Jones Golf Course in Palmetto Dunes. Vaulted ceilings, sizable windows, skylights and amazing vistas make this home one of the most inviting you will...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15