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Hilton Head, SC 5+ Bedroom Vacation Rentals

Filter 5+ Bedroom Hilton Head Properties by: Company | Oceanfront | Pet-Friendly | or choose different a Area or Bedrooms
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87 rentals found
Gorgeous new luxury beach house - be the...

This new, 5 bedroom, 5 ½ bath, home is a ideal fit for extended families, or as a multi-family vacation residence. Feel absolute luxury and convenience in this beautiful professionally decorated coastal beach home. As a guest at Serenity Now you...

  • Hilton Head
  • 5 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Enjoy panoramic lagoon views and private...

This gorgeous pet friendly home is thoughtfully designed with both comfort and style in mind. With an upsized porch overlooking the lagoon, sunny pool, and the ideal great room, this home is sure to impress.Upon entry you are greeted by an enormous...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
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
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 striking vistas make this home one of the most inviting you will...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
2 Min Walk 2 Beach. Walk 2 Pickleball Go...

Planning a December Family Getaway?Appreciate the magic of the season at our elegantly 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
Oceanfront, Private Beach Access

Located right on the Atlantic in the Sea Pines Plantation, 22 Black Skimmer Rd is frequently praised as a dreamy, family-friendly escape — the kind of place where you make lifelong memories. Guests consistently highlight its striking location...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
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 appreciate 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
Lovely house with gourmet kitchen, scree...

Summary:Black SkimmerThe Space:Savor the ultimate Hilton Head Island hideaway in this cavernous 5-bedroom, 5-bathroom Lowcountry beach home, charmingly located in the heart of Sea Pines Plantation. Walking paths and boardwalks give you fast and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
3 Shore Crest, Chefs Kitchen, Free Golf,...

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
10 Collier, Oceanfront, Elevator, Ping P...

10 Collier Beach, Hilton Head Island is an escape to heaven in this impressive 6-bedroom, 7-bathroom oceanfront home, offering beautiful ocean vistas and the ultimate in privacy. Unwind by the private pool, savor direct access to the beach, and...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
Large Private Home with Private Pool and...

You're going to be happy you chose this enormous home with plenty of room for your family to spread out! The kitchen is very nice with dark wood cabinets, stainless steel appliances, granite countertops and bar seating for five. Adjacent to the...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Expansive Private Oceanfront Home with V...

Fall in appreciate with this broad oceanfront home located on the Atlantic Ocean in striking Palmetto Dunes Oceanfront Resort! As you enter you are welcomed by a grandiose staircase and wood floors leading to the kitchen, dining and living areas. ...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
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
Stunning oceanfront home with pool, priv...

Summary:Dune Lane 105The Space:If you’ve been planning a group hideaway to Hilton Head but haven’t yet found the ideal place, stop scrolling - here it is. With an unbeatable oceanfront location just two miles from Coligny Beach Park, beach...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Second row to the ocean - 5 bedroom newl...

2nd Row Ocean! 5 Bedrooms, 4 Full baths, 2,500sq.ft. Next to Sea Pines Ocean gate.You will definitely fall in appreciate with this beautiful South Forest Beach home! The property is located right outside the Sea Pines ocean gate and is second row...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12