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Hilton Head, SC 5+ Bedroom Vacation Rentals

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93 rentals found
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
  • 5 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Luxurious home with private pool, centra...

Surf ScoterOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Surf Scoter offers luxury vacation rental at its best! This impressive multi-level home, located...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Sprawling coastal home with private pool...

Bradley Beach Road EstateOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Offering a memorable, family-friendly, coastal escape, this beautiful home is located...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
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, cavernous common areas, and plenty of beds to lay your head down at...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
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 huge staircase and wood floors leading to the kitchen, dining and living areas. The...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10
Ocean and Marsh View Home with private p...

Collier Court 4Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your dream hideaway in Hilton Head, SC! Just 50 feet from the beach path, this...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
Sunny & bright home near the beach w/ pr...

Sandhill Crane 3Our 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...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
31 Singleton  Oceanfront, Views, Luxury ...

***NOW OFFERING COMPLIMENTARY 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***31 Singleton Beach...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Second row to the ocean - 5 bedroom newl...

2nd Row Ocean! 5 Bedrooms, 4 Full baths, 2,500sq.ft. Next to Sea Pines Ocean gate.You will definitely fall in appreciate with this elegant South Forest Beach home! The property is located right outside the Sea Pines ocean gate and is second row to...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
5 Sandy Beach Trail- Beach House w/ Priv...

"Sail Away HHI" is a enormous 4500 square foot, 6 bedroom, 6 full bathroom (plus 1 half bath) home located steps away from the beach access. Located in the charming Burkes Beach community of Hilton Head Island, (rated as the best beaches in America...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 19
Amazing Oceanfront estate

New to Island GetawaySet along the shoreline with sweeping Atlantic vistas, this exceptional six-bedroom 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
Pet and Friendly Shipyard Home with 5 Be...

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
Spacious Home with Gourmet Kitchen, Priv...

Sea Oak Lane 5Our 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...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Private Oceanfront Home with Private Poo...

You'll adore this six bedroom oceanfront home located in esteemed Palmetto Dunes Oceanfront Resort. Boasting numerous sizable windows facing the oceanfront, this home provides oceanfront vistas from nearly every room! As you enter, you are first...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Beautiful ocean view house w/ private po...

Hidden in HiltonOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel beach living luxury at its best in this striking home located just 2 rows from the beach...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Large Private Home with Private Pool and...

You're going to be happy you chose this huge home with plenty of room for your family to spread out! The kitchen is very nice with dark wood cabinets, stainless steel appliances, granite countertops and bar seating for five. Adjacent to the...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Wonderful golf and lagoon views- Pet Fri...

VIEWS VIEW VIEWS! LOCATION! LOCATION! LOCATION!This near ocean home in Palmetto Dunes has it all, offering both privacy and painless access to the gorgeous coastline! As you enter the 2-story living room the sizable windows fill the room with...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Mediterranean Coastal 2nd Row 6 Bedroom ...

Located in the heart of Palmetto Dunes Oceanfront Resort on Hilton Head Island, this attractively refreshed 6-bedroom, second-row vacation home offers the ideal blend of luxury, space, and an unbeatable location. Just steps from the beach, guests...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 18