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Hilton Head, SC 5+ Bedroom Vacation Rentals

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96 rentals found
Luxury 6-Bedroom Home with Private Pool,...

Welcome to 99 Sandcastle Court, a extravagant coastal getaway constructed in 2020, located within the exclusive gated community of Sandcastles by the Sea on Hilton Head Island. Perfectly positioned just a short, breezy walk from the pristine sands...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
205 Jacana-\

**Luxurious 6-Bedroom Beach Home Just Steps from North Forest Beach!**Escape to your dream vacation in this roomy and delightfully designed 6-bedroom, 6.5-bath beach home, just a few sandy steps from the impressive North Forest Beach. Whether you're...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
2 Min Walk 2 Beach Pickleball Golf Tenni...

One of the very best located properties in Hilton Head. November and December are great for beach activities: golf, tennis, pickleball. Appreciate our private heated pool and spa.Book Christmas week and week before now while still available. Both...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Large Home with Panoramic Views of Rober...

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

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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
19 Sand Dollar, Luxury 2nd Row Home, Che...

19 Sand Dollar, Hilton Head Island. Welcome to this appealing second-row ocean home blending traditional coastal Carolina styling with high-end details for a memorable beach vacation! Located directly across from a semi private beach, appreciate...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
Oceanfront home with huge windows and a ...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This beautiful, nine-bedroom Beachcomber home sports a private pool and spa and provides broad living spaces, as well as astounding vistas of the beach and the...

  • Hilton Head
  • 9 Bedrooms
  • 10 Bathrooms
  • Sleeps 28
Lovely house with gourmet kitchen, scree...

Black SkimmerOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This property in the Sea Pines development sits among the natural beauty of Hilton Head Island's...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
Sandcastle by the Sea - brand-new, priva...

Sandcastle 97Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in a gated beachside community, Sandcastle by the Sea is a family-friendly 6BR/4BA...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Large Sprawling Home Very Close to the B...

This huge six bedroom and seven bathroom home has everything you'll need to provide a ideal vacation for your whole family! All furnishings in the entire home has been replaced and there are too many updates to name!The sprawling chef-style kitchen...

  • Hilton Head
  • 6 Bedrooms
  • 7 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 completely-equipped with everything you'll need to prepare a meal for your entire...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
44 Bradley Beach, Close to Beach, Large ...

44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 and has a huge 16' x 32' pool, and features an outdoor fire pit ideal for a nighttime hosting around the pool or a cool day in the fall! There is plenty of seating and...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Private home in Hilton Head Island with ...

Located within the esteemed Palmetto Dunes Oceanfront Resort on Hilton Head Island, this handsomely upgraded 5-bedroom, 3-bathroom home sits on a charming corner lot and offers the ideal blend of comfort, luxury, and coastal appeal.Step inside to an...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
60 Lawton Road, Sea Pines

Welcome to the BESTNEST at 60 Lawton Road in Sea Pines! Here's the skinny - just buzz us for more details: Our advertised prices are our very best rates and calendar shows real time availability. We encourage you to book online!• Charmingly...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Spacious Condo with WiFi, Wet Bar, & Wat...

Sound Villas 1458Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'It's hard to top this alluring and enormous island condo, offering striking vistas of the...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
Views of both the George Fazio Golf Cour...

A very sizable and beautiful home with extremely high vaulted ceilings with vistas of both the award winning George Fazio golf course and Palmetto Dunes' 11 mile lagoon system. Up the front steps you are greeted by a grandiose entry. As you enter...

  • Hilton Head
  • 5 Bedrooms
  • 5 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 elegantly decorated with comfort and the beach in mind. The kitchen is striking and...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Gorgeous 5 ?? custom home! 5 king suites...

Vacation in luxury in this alluring home! This 4500 square foot home is designed ideally for multiple families. Just a 3-5 min. walk to the beach, this home has everything you could ask for! With 7 bedrooms, 7 and 2 1/2 baths, 3 living rooms and...

  • Hilton Head
  • 7 Bedrooms
  • 8 Bathrooms
  • Sleeps 20