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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
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 magnificant property features 6 bedrooms and 8 bathrooms. The chef's kitchen features...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Stunning oceanfront home offering privat...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This gorgeous 5-bedroom, 5.5-bathroom oceanfront home is located in the heart of North Forest Beach, offering an memorable coastal experience with sweeping...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
North Forest Beach home with a private p...

Summary:Holloman Trace 23 Flip Flop PhilosophyThe Space:This freshly constructed, North Forest Beach ocean home is ready to host all of your favorite people! Located in North Forest Beach, this home features all of the luxuries you crave; a private...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
44 Bradley Beach, Close to Beach, Large ...

**New Bonus Room Off of the Pool and Updated Bathrooms!!**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...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Close to beach, pickleball, tennis & gol...

Summary:Flagg 2-Serene RetreatThe Space:You’ve found gold with this pretty, 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
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
Mediterranean Coastal 2nd Row 6 Bedroom ...

Located in the heart of Palmetto Dunes Oceanfront Resort on Hilton Head Island, this gorgeously refreshed 6-bedroom, second-row vacation home offers the ideal blend of luxury, space, and an unbeatable location. Just steps from the beach, guests...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 18
Gorgeous 5 ?? custom home! 5 king suites...

Vacation in luxury in this charming 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
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 impressive...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Spacious Home with Gourmet Kitchen, Priv...

Summary:Sea Oak Lane 5The Space:*Please read our important pool heat information to help you have the best vacation possible!*This property has a pool that can be heated between Labor Day and Memorial Day for an additional fee of $69/nighttime. You...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
New Pool! minutes to Hilton Heads best b...

This charming 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
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
Large Oceanfront Home with Private Pool ...

Treat your family with this immense five bedroom home located oceanfront on Catboat Lane within Palmetto Dunes Oceanfront Resort! The gourmet chef's kitchen will be entirely-equipped with everything you'll need to prepare a meal for your entire...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Bright & Expansive Beach Retreat with Pr...

Summary:Cartgate 21The Space:Freshly Updated, Roomy 6-Bedroom Retreat with Private Pool Near the BeachWelcome to your ideal Lowcountry escape—this elegantly refreshed, broad home offers six bedrooms and five bathrooms, comfortably accommodating up...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
This home has all the modern comforts to...

4 Cockle Ct. is a Stunning Coastal Chic Home just a 5 min. walk to the beach!Upon entering this open concept home you will immediately notice the striking architectural details of the archways and the high vaulted ceilings. When walking through the...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
1 Shore Crest, Large Pool, Ping Pong, Be...

1 Shore Crest Lane, Hilton Head Island is a handsome home constructed in 2022 and offers 5 bedrooms & 5 bathrooms, a enormous 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
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 appreciate their beach vacation. A one million dollar...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 17
2nd Row Palmetto Dunes home with private...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Step inside to an impressive, upsized entryway that immediately sets the tone for this exceptional home. The grandiose entrance features a sweeping spiral...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 16