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5+ Bedroom Vacation Rentals

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87 rentals found
Sunny & bright home near the beach with ...

Summary:Sandhill Crane 3The 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 $95/nighttime. At...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Large Six Bedroom Custom-Built Home with...

This home is designed to fit your next family vacation! The kitchen comes completely equipped to meet your family's cooking needs with stainless steel appliances and bespoke cabinetry, including two ovens and microwave. The sizable kitchen island...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Secluded Sea Pines retreat with private ...

Summary:Royal RetreatThe Space:Escape to this luxury estate boasting two separate poolside structures and generous seating areas inside and out - ideal for entertaining. The roomy and handsome property is under new ownership and has been...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 20
Sandcastle by the Sea - 3 blocks to beac...

Summary:Sandcastle 97The Space:Located in a gated beachside community, Sandcastle by the Sea is a family-friendly 6BR/4BA getaway that promises an elevated vacation experience. This brand-new home features high-end finishes paired with impressive...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
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 handsome professionally decorated coastal beach home. As a guest at Serenity Now you...

  • Hilton Head
  • 5 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
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
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
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
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
5 Bedroom Near Ocean Home

Tucked away just four rows from the ocean and directly across from a beach access path, this cavernous 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...

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

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

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
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 impressive 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
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 gorgeous home is located in the prime Folly Field Area...

  • Hilton Head
  • 6 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
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
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
2 Collier, Oceanfront, Dogs OK, Pool, Fr...

2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this gorgeous oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
60 Lawton Rd: Sea Pines

Welcome to the 5BR/4BA BESTNEST at 60 Lawton Road. Charmingly modernized and filled with natural light, this five-bedroom Sea Pines home offers generous gathering spaces, flexible accommodations, and a private pool overlooking the lagoon. A separate...

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