Hilton Head Island Vacation Rental Getaways


Refine Your Search
Check-In 
calendar

Check-Out
calendar
  • Property Options
  • Amenities
  • Location Type
  • Bed
  • Bath
  • Sleeps
Max Price Per Week $
  • Special Offers
  • Online Booking
  • Home/Villa
  • Cottage/Cabin
  • Condo/Townhome
  • Bed & Breakfast
  • Apt/Room/Suite
  • Air Conditioning
  • Washer/Dryer
  • Full Kitchen
  • Satellite/Cable TV
  • Handicap Access
  • High Speed Internet
  • Elevator
  • Maid Service
  • Garage Parking
  • Pets Allowed
  • Private Pool
  • Pool Access
  • Hot Tub
  • Fireplace
  • Smoking allowed
  • Beach Access
  • Beach Front
  • Golf on site
  • Golf nearby
  • Ocean Front
  • Ocean View
  • Lake Front
  • Lake View
  • Ski in/out
  • Walk to Slopes
  • Skiing nearby
 
Sort by: Type BR/BA/Sleeps Price

Beautiful Spotless 148 Windward Villa, Golf Views, Free B...

Hilton Head Island
Beautiful Spotless 148 Windward Villa, Golf Views, Free Bikes, Pool, Hot Tub This charming villa is...
Villa 2 / 2.5 / 4

*
Online booking available

$113 - $164
Per Night

$495 - $1095
Per Week

6 Portside- Fully Renovated / Fantastic views of Braddock...

Hilton Head Island
6 Portside- Fully Renovated / Fantastic views of Braddock Cove & Marina 6 Portside is one of only s...
Home 4 / 3 / 8

*
Online booking available

$1995 - $3895
Per Week

Seaside Villa 247 - 1 BR 1 BA Oceanside Flat Hilton Head, Sc

Hilton Head Island
Internet Access!!!! This villa offers a separate bedroom with a queen size bed, nicely equipped kit...
Condo 1 / 1 / 4

*
Online booking available

$89 - $165
Per Night

$345 - $825
Per Week

Racquet Club Villas 2330

Hilton Head Island
Racquet Club Villa 2330 is a one bedroom condo located just a short walk from Harbour Town in Sea Pi...
Condo 1 / 1 / 4

*
Online booking available

$130 - $355
Per Night

$665 - $2310
Per Week

Queens Grant 588

Hilton Head Island
Queens Grant 588 is a three bedroom condo located just a short walk from the beach and tennis center...
Condo 3 / 2 / 8

*
Online booking available

$180 - $370
Per Night

$910 - $1890
Per Week

Villamare 3133

Hilton Head Island
Villamare 3133 is an ocean view, three bedroom condo located in Palmetto Dunes. This condo is locate...
Villa 3 / 3 / 10

*
Online booking available

$430 - $925
Per Night

$2205 - $4655
Per Week

Island Club 5402, 2 Bedroom, Oceanfront, Large Pool, Slee...

Hilton Head Island
This 2 bedroom, 2 bathroom Island Club oceanfront 4th-floor villa also has one of the most awesome o...
Condo 2 / 2 / 8

*
Online booking available

$216 - $450
Per Night

$1195 - $2250
Per Week

Sand Dollar 31, 4 Bedrooms, Large Private Pool, Sleeps 12

Hilton Head Island
31 Sand Dollar Road in Folly Field is a Beach House with private pool only a 2-minute walk to the be...
Home 4 / 2 / 12

*
Online booking available

$319 - $784
Per Night

$1595 - $3921
Per Week

Moorings 71-72, 2 Bedrooms, Pool, Walk to Beach, Sleeps 8

Hilton Head Island
71-72 The Moorings in Palmetto Dunes is wonderfully located as it is a very short walk to the beach,...
Condo 2 / 2.5 / 8

*
Online booking available

$179 - $350
Per Night

$895 - $1750
Per Week

Fiddler's Cove 28C, 2 Bedroom, Sleeps 6, Pool

Hilton Head Island
Hilton Head Island's best-kept secret! You can experience an economic vacation near the beach, golf,...
Condo 2 / 2 / 6

*
Online booking available

$139 - $259
Per Night

$695 - $1295
Per Week

3 Braddock Cove Club-Beautiful View of Braddock Cove and ...

Hilton Head Island
3 Braddock Cove Club-Beautiful View of Braddock Cove and so much more..... This 4 Bedroom, 3.5 bath...
Villa 4 / 3.5 / 10

*
Online booking available

$995 - $2595
Per Week

2415 Seacrest-Wow Views! You can't beat these oceanviews.

Hilton Head Island
This beautiful 4th Floor 3 Bedroom, 3 Bath OCEANVIEW villa offers you a terrific view of the Atlanti...
Villa 3 / 3 / 9

*
Online booking available

$1395 - $3595
Per Week

77 Mooring Buoy-5th Row Ocean w/ Large pool & Lagoon View.

Hilton Head Island
Whippoorwill Cove - This 6,000 square foot 6 bedroom luxury home with **HEATED POOL and adjoining ca...
Home 6 / 6 / 14

*
Online booking available

$2995 - $8095
Per Week

Courtside 27 - Forest Beach Townhouse

Hilton Head Island
Courtside is an ocean-oriented complex with first-floor apartments, two-story and three-story townho...
Condo 2 / 2.5 / 6

*
Online booking available

$120 - $210
Per Night

$600 - $1050
Per Week

Sea Crest 2509 - Oceanview 5th Floor Condo

Hilton Head Island
Stay in an exceptional 5th floor oceanside condo within a newly built North Forest Beach oceanfront ...
Condo 3 / 3 / 9

*
Online booking available

$280 - $620
Per Night

$1400 - $3100
Per Week

2 Quail- 5th row ocean. Beautiful home! 7/8-15 Week Avail...

Hilton Head Island
2 Quail- 5th row ocean. Beautiful home! 7/8-15 Week Available Incredible custom built 5th Row to th...
Home 7 / 5.5 / 17

*
Online booking available

$3395 - $9295
Per Week

Seaside Villa 350 - 1 BR 1 BA Oceanside Flat Hilton Head, Sc

Hilton Head Island
Seaside 350 is a nicely furnished one bedroom, one bathroom Oceanside villa on the third floor of an...
Condo 1 / 1 / 6

*
Online booking available

$89 - $165
Per Night

$345 - $825
Per Week

2 BR Ocean View Villa with Spectacular Pool & Ocean Views!

Hilton Head Island
**Shorewood 536** This lovely villa offers all new furnishings, a top of the line Kitchen with Gr...
Villa 2 / 2 / 7

*
Online booking available

$240 - $350
Per Night

$1200 - $2500
Per Week

Village House 101, 2 Bedrooms, Pet Friendly, Pool, Sleeps 8

Hilton Head Island
101 Village House in Port Royal Plantation. This beautiful 2BR/2BA pet-friendly villa, located just ...
Condo 2 / 2 / 8

*
Online booking available

$114 - $241
Per Night

$750 - $1444
Per Week

St. Andrews Common 1751, 1 Bedroom, Ground Level, Large Pool

Hilton Head Island
St. Andrews Common 1751 in Palmetto Dunes. New to the program and ready to welcome you to your next ...
Condo 1 / 2 / 4

*
Online booking available

$119 - $230
Per Night

$595 - $1150
Per Week

Greens 102, 2 Bedroom, Large Pool, Golf View, Walk to Bea...

Hilton Head Island
The Greens 102 in Shipyard Plantation is a 2 bedroom, 2.5 bath villa that has been totally updated w...
Condo 2 / 2.5 / 6

*
Online booking available

$139 - $259
Per Night

$695 - $1295
Per Week

South Beach Lagoon 7, 5 Bedrooms, Ocean Front, Pool, Slee...

Hilton Head Island
Look no further, this is your Ocean Front Paradise! Nestled in the Heart of Sea Pine's Plantation, S...
Home 5 / 6.8 / 12

*
Online booking available

$742 - $2791
Per Night

$5195 - $16748
Per Week

Beachside Tennis 1895, 2 Bedrooms, Large Pool

Hilton Head Island
Beachside Tennis 1895 - The Ultimate Place for Vacation and Lovely Timeouts. Are you looking forwar...
Condo 2 / 2 / 6

*
Online booking available

$249 - $550
Per Night

$1350 - $2750
Per Week

77 Plantation Drive-Quick Walk to Harbour Town or Bike ri...

Hilton Head Island
77 Plantation Drive-Quick Walk to Harbour Town or Bike ride to the Beach. Beautifully decorated 4 b...
Home 4 / 4.5 / 8

*
Online booking available

$1495 - $14000
Per Week

Ocean One 307 - Oceanfront 3rd Floor Condo

Hilton Head Island
With decks off the living room and master bedroom, guests staying in Ocean One 307 enjoy panoramic v...
Condo 2 / 2 / 6

*
Online booking available

$220 - $460
Per Night

$1100 - $2300
Per Week

 

More Getaway Locations and Properties