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5+ Bedroom Vacation Rentals

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98 rentals found
Large Golf Course View Home with Large P...

This charming home features extravagant wide plank, hand-scraped, black walnut floor throughout the main living areas. This magnificant home consists of six bedrooms, six and a half bathrooms along with an elegant sunroom along with a enchanting...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
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 amazing property features 6 bedrooms and 8 bathrooms. The chef's kitchen features top-of-the-line...

  • Hilton Head
  • 6 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 freshly refreshed four-story property offers impressive...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Fabulous! Huge 5 Bedrm/5 Bath Moss Creek...

Moss Creek House Description This 4,500+ sq. ft. home, consisting of 5 bedrooms and 5 baths, that sleeps 12, is located in the pretty Moss Creek private club community. We have an in-ground, plunge pool with lion head water spouts, with the backdrop...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Modern home on 7th fairway with private ...

Yard Arm 2Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Relaxation awaits! Appreciate staying at this newly-constructed home overlooking the 7th fairway of...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Renovated spacious home with private poo...

Full Sweep 66Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This property has a pool that can be heated between Labor Day and Memorial Day for an additional...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Spacious house by the beach with screene...

Salt Air SanctuaryOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Just a fast walk down the street to Driessen Beach Park, this striking home in Hilton Head...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Gorgeous oceanfront beach home with priv...

Amazing oceanfront home…..your ideal vacation hideaway! This home is ideal for entertaining with eight bedrooms, eight full baths, 1 half bath and sizable living areas with huge flat screen TV's and calming sitting areas to appreciate the...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 21
Beautiful & Spacious House Near Beach w/...

Cartgate 21Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Freshly updated, roomy home with six bedrooms and five baths that accommodates up to 16 people...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Waterfront dream home with pool, lagoon ...

Shell Ring Road 63Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Peace and peaceful await you at this serene hideaway on Hilton Head Island. This home has a...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
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 enchanting professionally decorated coastal beach home. As a guest at Serenity Now you...

  • Hilton Head
  • 5 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Dog-friendly home with private pool, WiF...

Crabline Court 31Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find the ideal group hideaway at this family-friendly beach home, located just a half-mile...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Two-story home with pool, balcony, deck,...

Piping Plover 12Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Piping Plover 12 is an immaculate and striking 2nd row home located near South Beach in...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 20
Large Six Bedroom Custom-Built Home with...

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

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
7 Grey Widgeon Sea Pines -minutes to the...

True Southern Living at its best! This charming Sea Pines home was finished Spring of 2025. 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...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Beautiful home on the 11-mile lagoon sys...

Come savor this enormous five bedroom and five bathroom home located on Palmetto Dunes' 11-mile lagoon system! Located within the heart of Palmetto Dunes Oceanfront Resort, this home has been handsomely decorated throughout with wood floor and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
9 Singleton Beach, Newly Renovated, Ocea...

*New Construction Update(Spring 2025): Updated Kitchen, Updated Master Bathrooms, Updated Half Bathroom, (Jack n Jill Bathrooms to be refreshed winter 2025), New Washer and Dryer sets*9 Singleton Beach, Hilton Head Island. This oceanfront gem is a...

  • Hilton Head
  • 7 Bedrooms
  • 5 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 attractively decorated with comfort and the beach in mind. The kitchen is handsome and...

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