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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
Oceanfront home with huge windows and a ...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This handsome, 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 22
Elegant 5 Bedroom House

Step inside this charmingly appointed five-bedroom home, where roomy interiors, thoughtful coastal details, and exceptional outdoor living come together to create the ideal setting for a Hilton Head Island hideaway.As you enter the home, you are...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
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
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
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
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
Oceanfront, Pool, Views, Luxury, Elevato...

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
2nd Row Palmetto Dunes 5 Bed/5 Bath Home...

Located at the end of the street with direct beach path access from the pool, just 2 mins. from the pretty beaches of Palmetto Dunes, this home offers a great space for your next hideaway! Savor countless sunny days by the pool and calming evenings...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Unbeatable views from private pool with ...

Summary:Wren Drive 18The Space:Appreciate waking up to the sights and sounds of this lush island in the Lowcountry. This home is amazing for appreciating wildlife and nature! With broad vistas from every window of the marsh and Braddock Cove, you're...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
13 Moonshell, Close to Beach, Pool, Big ...

13 Moonshell Rd, Hilton Head is a ideal getaway for a coastal escape. With its five bedrooms and three bathrooms, it offers ample space for guests to relax and relax. The cavernous fenced backyard with a private pool and outdoor bar provides a...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
10 Iron Clad- Luxury Ocean Front Home, 6...

Welcome to 10 Iron Clad, a handsome 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
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
Modern home on 7th fairway with private ...

Summary:Yard Arm 2The Space:Relaxation awaits! Appreciate staying at this freshly-constructed home overlooking the 7th fairway of the Robert Trent Jones Golf Course, just a short walk or bicycle ride from the sugar sand beaches of Hilton Head...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
2 Collier, Oceanfront, Dogs OK, Pool, Fr...

***This home is undergoing a complete remodel, including a delightfully refreshed kitchen, bathrooms, pool, and pool deck. Stay tuned for a fresh new look throughout!***2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
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
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
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
Stunning Oceanfront Hideaway with Privat...

Summary:HeavenThe 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 MUST...

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