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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
5 Bedroom 4.5 Bathroom Updated Home

Welcome to your dream vacation home located in the heart of Palmetto Dunes Oceanfront Resort. This attractively appointed 5-bedroom, 4.5-bath offers the ideal blend of coastal appeal, modern comfort, and outdoor serenity ideal for creating memorable...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Palatial Home Just a Short Walk to the B...

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

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
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 gorgeous beaches of Palmetto Dunes, this home offers a great space for your next hideaway! Appreciate countless sunny days by the pool and calming...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
9 Promontory - Stunning PD Home w/ Golf ...

Welcome to this spectacular, upsized vacation home featuring soaring vaulted ceilings and memorable vistas of the award-winning George Fazio Golf Course and Palmetto Dunes’ breathtaking 11-mile lagoon system. From the grandiose entry to the broad...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
5 Bedroom Waterfront Home

Welcome to this roomy and versatile 5-bedroom vacation home, thoughtfully designed for families and groups looking to relax and reconnect. With generous living spaces and a welcoming ambiance, it's the ideal home base for your next hideaway.Inside...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
2 Min Walk 2 Beach. Walk 2 Pickleball Go...

Planning a December Family Getaway?Appreciate the magic of the season at our gorgeously decorated beach home in Palmetto Dunes. Take in the festive Christmas lights throughout Palmetto Dunes and all across Hilton Head Island, creating a excellent...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Elegant 5 Bedroom House

Step inside this gorgeously 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
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
424 Captains Walk has panoramic ocean vi...

This fourth floor penthouse in Captain's Walk is the ideal setting for your next vacation. Upon entering the unit, guests will savor expansive vistas of the Atlantic. The living room has two huge couches, game table, and TV. The dining room has...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 11
Wonderful golf and lagoon views- Pet Fri...

VIEWS VIEW VIEWS! LOCATION! LOCATION! LOCATION!This near ocean home in Palmetto Dunes has it all, offering both privacy and simple access to the pretty coastline! As you enter the 2-story living room the sizable windows fill the room with natural...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Sprawling coastal home with private pool...

Summary:Bradley Beach Road Estate - Sprawling coastal home with private pool, elevator, & spectacular lanai- dog-friendlyThe Space:Offering a memorable, family-friendly, coastal escape, this handsome home is located in the prime Folly Field Area...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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
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
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
Great Hilton Head Location Pet Friendly,...

This property is now under new ownership and the owners are keen to make this already gorgeous and roomy home lighter and brighter with a goal of blowing away all guests expectations! 4 Surf Watch Way is a elegant 6-bedroom, 5.5-bathroom, pet...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
North Forest Beach home with a private p...

Summary:Holloman Trace 23 Flip Flop PhilosophyThe Space:This newly 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
3rd row Ocean Luxury - Private Pool/Spa ...

Welcome to our luxury 7BR, 6.5BA coastal escape in North Forest Beach —just 75 steps or 3 mins. down a private path to the sand. Designed for multi-generational gatherings, this home features high-end furnishings, hotel-quality linens, a chef’s...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
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 gorgeous home into the open and inviting entryway. You are immediately greeted with...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 20