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Hilton Head, SC 5+ Bedroom Vacation Rentals

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93 rentals found
Oceanfront, Elevator, Ping Pong, Private...

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
6 Terra Bella, Oceanfront, Elevator, Pri...

**NOW OFFERING 50% OFF POOL HEAT FOR MARCH - MAY 22*** UPON BOOKING, GUEST MUST LEAVE IN COMMENTS THAT THEY WANT POOL/ SPA HEAT OR CALL OUR RESERVATIONS TEAM TO CONFIRM. THIS IS FOR NEW BOOKINGS MADE ON OR AFTER 1/30/26***6 Terra Bella Trace, Hilton...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Spacious waterview haven with decks, fir...

Sound Villas 1452Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'A roomy haven in the Sound Villas community, this family-friendly home is a sure bet for a...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Spacious Home - Private Pool & Big Deck ...

Mooring BuoyOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please read our important pool heat information to help you have the best vacation possible!*This...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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 28
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 newly refreshed four-story property offers striking ocean...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
8 Bedroom/8.5 Bathroom Large Luxurious H...

This cavernous 4th row Palmetto Dunes home is the ideal place for a huge family hideaway or golf trip! The beach path is directly across from the home and the multiple indoor and outdoor living spaces, this home makes for an ideal getaway for any...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 26
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
Amazing Family-Friendly House w/ Private...

High Water 9Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'An broad luxury home in Palmetto Dunes, High Water 9 features a single-level layout with seven...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 22
10 Iron Clad- Luxury Ocean Front Home, 6...

Welcome to 10 Iron Clad, a elegant 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 appreciate their beach vacation. A one million dollar...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 17
Ocean Views from Patio! Beautifully upda...

Curlew 8Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Curlew 8 is a opulent second-row private home featuring ocean vistas and chic, coastal décor. This...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 28
Spacious family home with WiFi, private ...

Summer HouseOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'With a fireplace, a pool, roomy common areas, and plenty of beds to lay your head down at...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
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
Spacious 2nd Row Palmetto Dunes home wit...

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
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
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. Appreciate high-end finishes, a chef's kitchen, sunroom, covered deck...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Amazing Oceanfront estate

Set along the shoreline with sweeping Atlantic vistas, this exceptional six-bedroom, 6900 sq foot, oceanfront residence captures the enduring appeal of classic Nantucket style paired with refined coastal luxury. Thoughtfully designed interiors...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Newly remodeled home with private pool a...

Feel the ultimate beach hideaway at this freshly modernized 5-bedroom, 4-bathroom home, ideally located just a less than 5 min. walk from the sand. Designed for effortless indoor-outdoor living, this property offers everything you need for a calming...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 9
Large Home with Panoramic Views of Rober...

Savor sweeping expansive vistas of multiple greens of the Robert Trent Jones Golf Course and a huge part of the 11 mile lagoon system! See the sunrise over the iconic 10th hole of Robert Trent Jones every morning! There are impressive vistas from...

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