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Hilton Head, SC 5+ Bedroom Vacation Rentals

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87 rentals found
424 Captains Walk has panoramic ocean vi...

This fourth floor penthouse in Captain's Walk is the ideal setting for your next vacation. Upon entering the unit, guests will appreciate expansive vistas of the Atlantic. The living room has two enormous couches, game table, and TV. The dining room...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 11
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 impressive...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Stunning oceanfront home offering privat...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.This striking 5-bedroom, 5.5-bathroom oceanfront home is located in the heart of North Forest Beach, offering an memorable coastal experience with sweeping...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
This home has all the modern comforts to...

4 Cockle Ct. is a Sensational Coastal Chic Home just a 5 min. walk to the beach!Upon entering this open concept home you will immediately notice the impressive architectural details of the archways and the high vaulted ceilings. When walking through...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 13
Beachfront home with private pool, expan...

Summary:Dunes HouseThe Space:Savor life at the beach at Dunes House! This home has impressive vistas of the beach and the Atlantic Ocean. The open living space on the second floor has living, dining, and a well-equipped kitchen that all look out to...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Elegant 5 Bedroom House

Step inside this gorgeously appointed five-bedroom home, where roomy interiors, thoughtful coastal details, and exceptional outdoor living come together to create the ideal setting for a Hilton Head Island hideaway.As you enter the home, you are...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
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
13 Moonshell, Close to Beach, Pool, Big ...

13 Moonshell Rd, Hilton Head is a ideal getaway for a coastal escape. With its five bedrooms and three bathrooms, it offers ample space for guests to relax and relax. The cavernous fenced backyard with a private pool and outdoor bar provides a...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Spacious Modern Getaway with Private Poo...

Summary:Full Sweep 66The Space:This elegant, modern home showcases high-end finishes throughout and is charmingly located just a 10-min. walk from the pristine beaches of Hilton Head Island. “Full Sweep” offers the ideal blend of comfort, style...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Large Home with Spectacular Panoramic Vi...

You're going to appreciate this huge home with spectacular expansive vistas of Robert Trent Jones Golf Course and the 11 Mile Lagoon! From when you first pull up to the home you'll notice it's very private with a modest fenced-in garden in the...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
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. Savor high-end finishes, a chef's kitchen, sunroom, covered deck, pool...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Fall Winter Escape: Value for Golf/Tenni...

This striking, 5 bedroom, 4.5 bathroom three story home is located in the most gorgeous area of Harbour Town. It sits between the Lighthouse and the 16th green of Harbour Town Links Golf Course, just off the 18th fairway and Calibogue Sound, in the...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Luxury 2nd Row Home, Chefs Kitchen, Pool...

19 Sand Dollar, Hilton Head Island. Welcome to this striking 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
Two-story home with pool, balcony, deck,...

Summary:Piping Plover 12The Space:Piping Plover 12 is an immaculate and impressive 2nd row home located near South Beach in beloved Sea Pines Plantation. Enter this handsome home into the open and inviting entry. You are immediately greeted with the...

  • Hilton Head
  • 6 Bedrooms
  • 5 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 pretty 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
44 Bradley Beach, Close to Beach, Large ...

**New Bonus Room Off of the Pool and Updated Bathrooms!!**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...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
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
5 Bedroom Near Ocean Home

Tucked away just four rows from the ocean and directly across from a beach access path, this cavernous 5 bedroom, 4 bathroom home offers the ideal blend of comfort, privacy, and unbeatable location.As you enter, you’re greeted by an open floor...

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