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Hilton Head, SC 5+ Bedroom Vacation Rentals

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101 rentals found
12 Whelk, Steps to the Beach, Private Po...
4.3
(12)

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 remodeled four-story property offers gorgeous ocean...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
18 Sand Dollar, Oceanfront, Pool, Hot Tu...
4.8
(32)

18 Sand Dollar, Hilton Head Island. Your search for the ideal vacation rental ends here! With 7 bedrooms, 7 bathrooms, and an open-concept floor plan, this property is sure to impress. The upsized chef's kitchen is ideal for cooking up delicious...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
Stunning oceanfront home with pool, priv...

Dune Lane 105Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you’ve been planning a group hideaway to Hilton Head but haven’t yet found the ideal...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
2 Collier Beach, Oceanfront, Dogs OK, Po...
3.8
(10)

2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this grand 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 private...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Spacious waterview haven with decks, fir...
4.8
(8)

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 cavernous haven in the Sound Villas community, this family-friendly home is a sure bet for...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Unbeatable views from private pool with ...
4.3
(12)

Wren Drive 18Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Savor waking up to the sights and sounds of this lush island in the Lowcountry. This home is...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
44 Mooring Buoy- 3rd Row (176 yard walk)...
4.7
(15)

You can practically feel the sand between your toes! This Palmetto Dunes island beauty is at the end of the beach path, so you’re just a few flip-flops or barefoot steps to the ocean and fun in the sun. The first-floor living area has a striking...

  • 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 impressive 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
6 Terra Bella, Oceanfront, Elevator, Pri...
4.7
(26)

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 impressive property features 6 bedrooms and 8 bathrooms. The chef's kitchen features...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
1 Shore Crest, Large Pool, Ping Pong, Be...
4.8
(4)

1 Shore Crest Lane, Hilton Head Island is a impressive home constructed in 2022 and offers 5 bedrooms & 5 bathrooms, a huge pool and a calming outdoor entertainment space. This splendid beach home is just a fast 3-5 min. walk to the Burkes Beach, is...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
2 Min Walk 2 Beach Pickleball Golf Tenni...
5.0
(110)

One of the very best located properties in Palmetto Dunes. Walk everywhere. Ideal vacation location! Two min. walk to tennis and pickleball courts, eateries and Trent Jones golf course on award winning Palmetto Dunes Plantation. Fazio and Arthur...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
4 Collier Ct, Oceanview, Pool, Elevator,...
4.5
(2)

4 Collier Court, Hilton Head Island is a property that is boasting fresh paint and décor enhancements updates, this home is a true gem. Just 50 feet from the beach path, it offers pretty vistas of the ocean and marsh. With 6 bedrooms, 6.5...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
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 entirely-equipped with everything you'll need to prepare a meal for your entire...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
New to the rental market, 4th row home!

This lagoon front Hilton Head Island home is located directly across the street from the beach access point and sits on one of the biggest tons in Palmetto Dunes Oceanfront Resort. The back deck is the ideal spot to appreciate the coastal breeze and...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Pet and Friendly Shipyard Home with 5 Be...
4.8
(4)

3 Port Au Prince is a excellent 5 bedroom, 3.5 bath, pet friendly home located in the gated community of Shipyard Plantation. The completely equipped kitchen has granite countertops, new range, island that seats 3, and breakfast table for six...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Views of both the George Fazio Golf Cour...
5.0
(1)

A very sizable and pretty 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 entryway. As you enter...

  • Hilton Head
  • 5 Bedrooms
  • 5 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 handsome professionally decorated coastal beach home. As a guest at Serenity Now you...

  • Hilton Head
  • 5 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Spacious Home - Private Pool & Big Deck ...
4.2
(20)

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